ACS Publications. Most Trusted. Most Cited. Most Read

OR SEARCH CITATIONS

My Activity
Publications
CONTENT TYPES

Figure 1Loading Img
Download Hi-Res ImageDownload to MS-PowerPointCite This:J. Am. Chem. Soc. 2010, 132, 40, 14048-14051
RETURN TO ISSUEPREVCommunicationNEXT
ADDITION / CORRECTIONThis article has been corrected. View the notice.

Synthesis of Heterocycles via Pd-Ligand Controlled Cyclization of 2-Chloro-N-(2-vinyl)aniline: Preparation of Carbazoles, Indoles, Dibenzazepines, and Acridines

View Author Information
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139
[email protected]
Cite this: J. Am. Chem. Soc. 2010, 132, 40, 14048–14051
Publication Date (Web):September 21, 2010
https://doi.org/10.1021/ja107511g
Copyright © 2010 American Chemical Society
Request reuse permissions

    Article Views

    9049

    Altmetric

    -

    Citations

    175
    LEARN ABOUT THESE METRICS
    Read OnlinePDF (2 MB)
    Get e-Alerts
    Supporting Info (1)»
    SUBJECTS:

    Abstract

    Abstract Image

    The Pd-catalyzed condensation of 2-bromostyrene and 2-chloroaniline derivatives yields stable diphenylamine intermediates, which are selectively converted to five-, six-, or seven-membered heteroaromatics (indoles, carbazoles, acridines, and dibenzazepines). The selectivity of these intramolecular transformations is uniquely ligand-controlled and offers efficient routes to four important classes of heterocycles from a common precursor.

    Supporting Information

    ARTICLE SECTIONS
    Jump To

    Experimental details for the synthesis of all new compounds and spectral data. This information is available free via the Internet at http://pubs.acs.org.

    Terms & Conditions

    Most electronic Supporting Information files are available without a subscription to ACS Web Editions. Such files may be downloaded by article for research use (if there is a public use license linked to the relevant article, that license may permit other uses). Permission may be obtained from ACS for other uses through requests via the RightsLink permission system: http://pubs.acs.org/page/copyright/permissions.html.

    Cited By

    This article is cited by 175 publications.

    1. Yuan-Yang Guo, Ze-Hua Tian, Luying Wang, Zheng-De Lai, Lingjun Li, Yong-Quan Li. Chemoenzymatic Synthesis of Phenol Diarylamine Using Non-Heme Diiron N-Oxygenase. ACS Catalysis 2023, 13 (2) , 1412-1417. https://doi.org/10.1021/acscatal.2c05190
    2. Kairui Yue, Simin Sun, Geng Jia, Mengting Qin, Xiaohan Hou, C. James Chou, Chao Huang, Xiaoyang Li. First-in-Class Hydrazide-Based HDAC6 Selective Inhibitor with Potent Oral Anti-Inflammatory Activity by Attenuating NLRP3 Inflammasome Activation. Journal of Medicinal Chemistry 2022, 65 (18) , 12140-12162. https://doi.org/10.1021/acs.jmedchem.2c00853
    3. Jiaping Wu, Yanfei Liu, Baiyang Qian, Haitao Yang, Lili Lu, Jitan Zhang, Yongjia Shang. Catalytic Ring Expansion of Indole toward Dibenzoazepine Analogues Enabled by Cationic Palladium(II) Complexes. ACS Catalysis 2022, 12 (10) , 6216-6226. https://doi.org/10.1021/acscatal.1c06021
    4. Qian Li, Chady Moussallem, Frédéric Castet, Luca Muccioli, Marie-Anne Dourges, Thierry Toupance, Yohann Nicolas. Direct Triple Annulations: A Way to Design Large Triazastarphenes with Intertwined Hexagonal Packing. Organic Letters 2022, 24 (1) , 344-348. https://doi.org/10.1021/acs.orglett.1c04001
    5. Santosh J. Gharpure, Pankaj E. Hande, Surya K. Pandey, Ganesh Samala. TMSOTf-Mediated Formal [4 + 2] Cycloaddition–Retro-aza-Michael Cascade of Vinylogous Carbamates for the Synthesis of Highly Fluorescent Pyridocarbazoles. The Journal of Organic Chemistry 2021, 86 (23) , 16652-16665. https://doi.org/10.1021/acs.joc.1c01927
    6. Min-Jie Zhou, Lei Zhang, Guixia Liu, Chen Xu, Zheng Huang. Site-Selective Acceptorless Dehydrogenation of Aliphatics Enabled by Organophotoredox/Cobalt Dual Catalysis. Journal of the American Chemical Society 2021, 143 (40) , 16470-16485. https://doi.org/10.1021/jacs.1c05479
    7. Su San Jang, Young Ho Kim, So Won Youn. Divergent Syntheses of Indoles and Quinolines Involving N1–C2–C3 Bond Formation through Two Distinct Pd Catalyses. Organic Letters 2020, 22 (23) , 9151-9157. https://doi.org/10.1021/acs.orglett.0c02898
    8. Andrew N. Dinh, Sean M. Maddox, Sagar D. Vaidya, Mirza A. Saputra, Christopher J. Nalbandian, Jeffrey L. Gustafson. Catalyst-Controlled Regioselective Chlorination of Phenols and Anilines through a Lewis Basic Selenoether Catalyst. The Journal of Organic Chemistry 2020, 85 (21) , 13895-13905. https://doi.org/10.1021/acs.joc.0c01917
    9. Xuanzeng Ye, Beihang Xu, Jiani Sun, Ling Dai, Yinlin Shao, Yetong Zhang, Jiuxi Chen. Pd-Catalyzed Approach for Assembling 9-Arylacridines via a Cascade Tandem Reaction of 2-(Arylamino)benzonitrile with Arylboronic Acids in Water. The Journal of Organic Chemistry 2020, 85 (20) , 13004-13014. https://doi.org/10.1021/acs.joc.0c01654
    10. Jacob M. Ganley, Philip R. D. Murray, Robert R. Knowles. Photocatalytic Generation of Aminium Radical Cations for C–N Bond Formation. ACS Catalysis 2020, 10 (20) , 11712-11738. https://doi.org/10.1021/acscatal.0c03567
    11. Xu Chen, Jin Lin, Biao Wang, Xu Tian. Nickel-Catalyzed Mizoroki–Heck/Amination Cascade Reactions of o-Dihaloarenes with Allylamines: Synthesis of Indoles. Organic Letters 2020, 22 (19) , 7704-7708. https://doi.org/10.1021/acs.orglett.0c02909
    12. Zifeng Cao, Yuan Zhu, Xiaoman Li, Yang He, Jinli Zhang, Liang Xu, Yu Wei. tert-Butyl Bromide-Promoted Intramolecular Cyclization of 2-Arylamino Phenyl Ketones and Its Combination with Cu-Catalyzed C–N Coupling: Synthesis of Acridines at Room Temperature. The Journal of Organic Chemistry 2020, 85 (15) , 10167-10174. https://doi.org/10.1021/acs.joc.0c00137
    13. Ryoya Miura, Shinsuke Goto, Takahide Hashimoto, Iwao Hachiya. Synthesis of 2,3-Disubstituted 4-Ethoxycarbonyl-β-carbolin-1-ones: Application to the Synthesis of SL651498 and Its Analogue. ACS Omega 2020, 5 (25) , 15631-15656. https://doi.org/10.1021/acsomega.0c01854
    14. Mamoru Ito, Moeka Okamura, Kyalo Stephen Kanyiva, Takanori Shibata. Catalytic Enantioselective Synthesis of Azepine-Fused Planar-Chiral Ferrocenes by Pt-Catalyzed Cycloisomerization. Organometallics 2019, 38 (20) , 4029-4035. https://doi.org/10.1021/acs.organomet.9b00422
    15. Iratxe Barbolla, Nuria Sotomayor, Esther Lete. Carbopalladation/Suzuki Coupling Cascade for the Generation of Quaternary Centers: Access to Pyrrolo[1,2-b]isoquinolines. The Journal of Organic Chemistry 2019, 84 (16) , 10183-10196. https://doi.org/10.1021/acs.joc.9b01357
    16. Anton S. Makarov, Maxim G. Uchuskin, Vladimir Gevorgyan. Intramolecular Palladium-Catalyzed Oxidative Amination of Furans: Synthesis of Functionalized Indoles. The Journal of Organic Chemistry 2018, 83 (22) , 14010-14021. https://doi.org/10.1021/acs.joc.8b02470
    17. Hao Wu, Zhiguo Zhang, Nana Ma, Qingfeng Liu, Tongxin Liu, Guisheng Zhang. Synthesis of Acridines from o-Aminoaryl Ketones and Arylboronic Acids by Copper Trifluoroacetate-Mediated Relay Reactions. The Journal of Organic Chemistry 2018, 83 (20) , 12880-12886. https://doi.org/10.1021/acs.joc.8b01828
    18. Alexandre A. Mikhailine, Gabriela A. Grasa Mannino, Thomas J. Colacot. Catalyst-Directed Chemoselective Double Amination of Bromo-chloro(hetero)arenes: A Synthetic Route toward Advanced Amino-aniline Intermediates. Organic Letters 2018, 20 (8) , 2301-2305. https://doi.org/10.1021/acs.orglett.8b00646
    19. Jixiang Ni, Yong Jiang, Zhenyu An, Rulong Yan. Cleavage of C–C Bonds for the Synthesis of C2-Substituted Quinolines and Indoles by Catalyst-Controlled Tandem Annulation of 2-Vinylanilines and Alkynoates. Organic Letters 2018, 20 (6) , 1534-1537. https://doi.org/10.1021/acs.orglett.8b00260
    20. Ruixia Yu, Dejun Li, and Fanlong Zeng . Palladium-Catalyzed Sequential Vinylic C–H Arylation/Amination of 2-Vinylanilines with Aryl boronic Acids: Access to 2-Arylindoles. The Journal of Organic Chemistry 2018, 83 (1) , 323-329. https://doi.org/10.1021/acs.joc.7b02728
    21. Heather Lam, Jennifer Tsoung, and Mark Lautens . Synthesis of Pyridobenzazepines Using a One-Pot Rh/Pd-Catalyzed Process. The Journal of Organic Chemistry 2017, 82 (12) , 6089-6099. https://doi.org/10.1021/acs.joc.7b00568
    22. Borja Cendón, Noelia Casanova, Cezar Comanescu, Rebeca García-Fandiño, Andrés Seoane, Moisés Gulías, and José L. Mascareñas . Palladium-Catalyzed Formal (5 + 2) Annulation between ortho-Alkenylanilides and Allenes. Organic Letters 2017, 19 (7) , 1674-1677. https://doi.org/10.1021/acs.orglett.7b00467
    23. Shilpi Pal, Deepak Choudhary, Mohit Jainth, Sonu Kumar, Rakesh K. Tiwari, and Akhilesh K. Verma . Regio- and Stereoselective Domino Synthesis of Oxazolo Fused Pyridoindoles and Benzofurooxazolo Pyridines from ortho-Alkynylarylaldehydes. The Journal of Organic Chemistry 2016, 81 (19) , 9356-9371. https://doi.org/10.1021/acs.joc.6b02062
    24. Jia Zheng, Zun Li, Liangbin Huang, Wanqing Wu, Jianxiao Li, and Huanfeng Jiang . Palladium-Catalyzed Intermolecular Aerobic Annulation of o-Alkenylanilines and Alkynes for Quinoline Synthesis. Organic Letters 2016, 18 (15) , 3514-3517. https://doi.org/10.1021/acs.orglett.6b01008
    25. Firouz Matloubi Moghaddam, Ghazal Tavakoli, Borna Saeednia, Peter Langer, and Behzad Jafari . Palladium-Catalyzed Carbamate-Directed Regioselective Halogenation: A Route to Halogenated Anilines. The Journal of Organic Chemistry 2016, 81 (9) , 3868-3876. https://doi.org/10.1021/acs.joc.6b00329
    26. Yelena Mostinski, Viviana Valerio, David Lankri, and Dmitry Tsvelikhovsky . Synthesis of Tricyclic Spiranoid Lactones via I2/Sm(II)- and I2/Pd(0)-Mediated Cyclizations of a Common Cycloalkylmethylene Precursor. The Journal of Organic Chemistry 2015, 80 (21) , 10464-10473. https://doi.org/10.1021/acs.joc.5b01278
    27. Alberto Hernán-Gómez, Emma Herd, Marina Uzelac, Thomas Cadenbach, Alan R. Kennedy, Ivana Borilovic, Guillem Aromı́, and Eva Hevia . Zincate-Mediated Arylation Reactions of Acridine: Pre- and Postarylation Structural Insights. Organometallics 2015, 34 (11) , 2614-2623. https://doi.org/10.1021/om501251q
    28. Stefan Ortgies and Alexander Breder . Selenium-Catalyzed Oxidative C(sp2)–H Amination of Alkenes Exemplified in the Expedient Synthesis of (Aza-)Indoles. Organic Letters 2015, 17 (11) , 2748-2751. https://doi.org/10.1021/acs.orglett.5b01156
    29. Yin-Long Li, Jian Li, Ai-Lun Ma, Ya-Nan Huang, and Jun Deng . Metal-Free Synthesis of Indole via NIS-Mediated Cascade C–N Bond Formation/Aromatization. The Journal of Organic Chemistry 2015, 80 (8) , 3841-3851. https://doi.org/10.1021/acs.joc.5b00090
    30. Shivaji B. Markad and Narshinha P. Argade . Diversity Oriented Convergent Access for Collective Total Synthesis of Bioactive Multifunctional Carbazole Alkaloids: Synthesis of Carbazomycin A, Carbazomycin B, Hyellazole, Chlorohyellazole, and Clausenaline D. Organic Letters 2014, 16 (20) , 5470-5473. https://doi.org/10.1021/ol502721r
    31. Ju Hyun Kim, Suh Young Choi, Jean Bouffard, and Sang-gi Lee . Tandem One-Pot Synthesis of Polysubstituted NH-Pyrroles Involving the Palladium-Catalyzed Intramolecular Oxidative Amination of the Zinc Bromide Complex of β-Enamino Esters. The Journal of Organic Chemistry 2014, 79 (19) , 9253-9261. https://doi.org/10.1021/jo501672c
    32. Young Ho Jang and So Won Youn . Metal-Free C–H Amination for Indole Synthesis. Organic Letters 2014, 16 (14) , 3720-3723. https://doi.org/10.1021/ol5015398
    33. Vanessa Narbonne, Pascal Retailleau, Giovanni Maestri, and Max Malacria . Diastereoselective Synthesis of Dibenzoazepines through Chelation on Palladium(IV) Intermediates. Organic Letters 2014, 16 (2) , 628-631. https://doi.org/10.1021/ol403525c
    34. Qing Su, Pei Li, Mina He, Qiaolin Wu, Ling Ye, and Ying Mu . Facile Synthesis of Acridine Derivatives by ZnCl2-Promoted Intramolecular Cyclization of o-Arylaminophenyl Schiff Bases. Organic Letters 2014, 16 (1) , 18-21. https://doi.org/10.1021/ol402732n
    35. Jennifer Tsoung, Jane Panteleev, Matthias Tesch, and Mark Lautens . Multicomponent-Multicatalyst Reactions (MC)2R: Efficient Dibenzazepine Synthesis. Organic Letters 2014, 16 (1) , 110-113. https://doi.org/10.1021/ol4030925
    36. Hai-Ming Guo, Run-Ze Mao, Qiao-Tian Wang, Hong-Ying Niu, Ming-Sheng Xie, and Gui-Rong Qu . Pd(II)-Catalyzed One-Pot, Three-Step Route for the Synthesis of Unsymmetrical Acridines. Organic Letters 2013, 15 (21) , 5460-5463. https://doi.org/10.1021/ol402596g
    37. Takanori Matsuda and Shinya Sato . Synthesis of Dibenzoheteropines of Group 13–16 Elements via Ring-Closing Metathesis. The Journal of Organic Chemistry 2013, 78 (7) , 3329-3335. https://doi.org/10.1021/jo4001993
    38. Gong M. Chu, Israel Fernández, and Miguel A. Sierra . Control over the E/Z Selectivity of the Catalytic Dimerization of Group 6 (Fischer) Metal Carbene Complexes. The Journal of Organic Chemistry 2013, 78 (3) , 865-871. https://doi.org/10.1021/jo302130h
    39. Daniel Solé, Francesco Mariani, Israel Fernández, and Miguel A. Sierra . Intramolecular Pd(0)-Catalyzed Reactions of (2-Iodoanilino)-aldehydes: A Joint Experimental–Computational Study. The Journal of Organic Chemistry 2012, 77 (22) , 10272-10284. https://doi.org/10.1021/jo301924e
    40. Thomas M. Gøgsig, Jonatan Kleimark, Sten O. Nilsson Lill, Signe Korsager, Anders T. Lindhardt, Per-Ola Norrby, and Troels Skrydstrup . Mild and Efficient Nickel-Catalyzed Heck Reactions with Electron-Rich Olefins. Journal of the American Chemical Society 2012, 134 (1) , 443-452. https://doi.org/10.1021/ja2084509
    41. Chin-Chau Chen, Shyh-Chyun Yang, and Ming-Jung Wu . Iodine-Mediated Cascade Cyclization of Enediynes to Iodinated Benzo[a]carbazoles. The Journal of Organic Chemistry 2011, 76 (24) , 10269-10274. https://doi.org/10.1021/jo201795t
    42. Emma-Claire Elliott, Elizabeth R. Bowkett, James L. Maggs, John Bacsa, B. Kevin Park, Sophie L. Regan, Paul M. O’Neill, and Andrew V. Stachulski . Convenient Syntheses of Benzo-Fluorinated Dibenz[b,f]azepines: Rearrangements of Isatins, Acridines, and Indoles. Organic Letters 2011, 13 (20) , 5592-5595. https://doi.org/10.1021/ol202318w
    43. So Won Youn, Joon Hyung Bihn, and Byung Seok Kim . Pd-Catalyzed Intramolecular Oxidative C–H Amination: Synthesis of Carbazoles. Organic Letters 2011, 13 (14) , 3738-3741. https://doi.org/10.1021/ol201416u
    44. Yameng Wan, Xiaoqiang Gao, Ruiai Wang, Fanfan Li, Yanxun Li, Haixia He. Research on solubility behavior of iminostilbene in twelve mono-solvents: Measurement, modeling, molecular simulation and thermodynamic properties. The Journal of Chemical Thermodynamics 2024, 188 , 107182. https://doi.org/10.1016/j.jct.2023.107182
    45. Suman Bhatta, Bidyut Kumar Senapati, Sanjib Kumar Patra, Samik Nanda. A sequential Friedländer and anionic benzannulation strategy for the regiodefined assembly of unsymmetrical acridines. Organic & Biomolecular Chemistry 2023, 21 (43) , 8727-8738. https://doi.org/10.1039/D3OB01470C
    46. Hideto Ito, Kou P. Kawahara, Kenichiro Itami. Heteroatom-Embedding Annulative π-Extension (Hetero-APEX) Reactions: An Overview. Synthesis 2023, 117 https://doi.org/10.1055/a-2169-4078
    47. Carmen Margaret White, Naranchimeg Zorigt, Tianning Deng, Tom G. Driver. Iodine(III)‐Mediated Oxidation of Anilines to Construct Dibenzazepines**. Chemistry – A European Journal 2023, 29 (37) https://doi.org/10.1002/chem.202301141
    48. Xin‐Chen Zhan, Guo‐Qiang Lin, Jian‐Guo Fu, Xiao‐Ming Ji, Shu‐Sheng Zhang, Chen‐Guo Feng. Synthesis of Dibenzo[ b , f ]azepines via Palladium‐Catalyzed Cascade [4 + 3] Annulation of o ‐Alkenyl Bromoarenes and o ‐Bromoaniline Derivatives. Advanced Synthesis & Catalysis 2023, 57 https://doi.org/10.1002/adsc.202300336
    49. David Irving Hermann Maier, Barend Christiaan Buurman Bezuidenhoudt, Charlene Marais. Strategies in the synthesis of dibenzo[ b,f ]heteropines. Beilstein Journal of Organic Chemistry 2023, 19 , 700-718. https://doi.org/10.3762/bjoc.19.51
    50. Zahra Souri, Mahmood Masoudi Khoram, Davood Nematollahi, Mohammad Mazloum-Ardakani, Hojjat Alizadeh. A green protocol for the electrochemical synthesis of a fluorescent dye with antibacterial activity from imipramine oxidation. Scientific Reports 2022, 12 (1) https://doi.org/10.1038/s41598-022-08770-4
    51. Jingran Zhang, Beibei Zhang, Jiaxin He, Haofeng Shi, Yunfei Du. Divergent synthesis of 2-methylthioindole and 2-unsubstituted indole derivatives mediated by SOCl 2 and dimethyl/diethyl sulfoxides. Organic & Biomolecular Chemistry 2022, 20 (40) , 7886-7890. https://doi.org/10.1039/D2OB01580C
    52. Morad Avarsaji, Zinatossadat Hossaini, Ali Varasteh Moradi, Hamid Reza Jalilian, Ramin Zafar Mehrabian. Synthesis and Biological Activity Investigation of New Oxazolopyrimidoazepine Derivatives: Application of Ag/Fe 3 O 4 /TiO 2 /CuO@MWCNTs MNCs in the Reduction of Organic Pollutants. Polycyclic Aromatic Compounds 2022, 6 , 1-22. https://doi.org/10.1080/10406638.2022.2110903
    53. Ryoko Tanaka, Ayana Nabae, Koki Yamane, Kosho Makino, Hidetsugu Tabata, Tetsuta Oshitari, Hideaki Natsugari, Hideyo Takahashi. Atropisomeric Properties of N-Alkyl/Aryl 5H-Dibenz[b,f]azepines. Chemical and Pharmaceutical Bulletin 2022, 70 (8) , 573-579. https://doi.org/10.1248/cpb.c22-00265
    54. Liuyang Deng, Ranran Guo, Lianjie Wang, Cao Yang, Zechao Wang. Rapid construction of acridines via BF3•Et2O promoted cyclization of 2-phenylamino benzophenones. Tetrahedron Letters 2022, 105 , 154044. https://doi.org/10.1016/j.tetlet.2022.154044
    55. Hiroyoshi Masuda, Hiroki Morishita, Rikuto Sasaki, Kaito Takahata, Kento Uemura, Iwao Hachiya. Synthesis of 2,3,6‐Trisubstituted β‐Carbolin‐1‐ones Utilizing 3‐Amino‐2‐pyridone Synthesis. ChemistrySelect 2022, 7 (21) https://doi.org/10.1002/slct.202201737
    56. Kota Fukuoka, Katsutoshi Imai, Kotaro Hirano, Shinsuke Goto, Ryoya Miura, Iwao Hachiya. Synthesis of 3,6‐Disubstituted 4‐Ethoxycarbonylpyranoindol‐1‐ones Utilizing 3‐Amino‐2‐pyrone Synthesis. Asian Journal of Organic Chemistry 2022, 11 (6) https://doi.org/10.1002/ajoc.202200110
    57. Rumpa Sarkar, Surya Kanta Samanta, Avantika Hasija, Deepak Chopra, Debabani Ganguly, Mrinal K. Bera. A practical route to arylated dihydroacridine derivatives via nickel boride mediated intramolecular reductive cyclization-concomitant dehydration. New Journal of Chemistry 2022, 46 (15) , 7168-7176. https://doi.org/10.1039/D1NJ05196B
    58. Frank Hochberger-Roa, Perla H. García-Ríos, José G. López-Cortés, M. Carmen Ortega-Alfaro, Jean-Claude Daran, Maryse Gouygou, Martine Urrutigoïty. Interrupted Intramolecular Hydroaminomethylation of N-Protected-2-vinyl Anilines: Novel Access to 3-Substitued Indoles or Indoline-2-ols. Molecules 2022, 27 (3) , 1074. https://doi.org/10.3390/molecules27031074
    59. Alexander Haydl, Arne Geissler, Dino Berthold. Metal-Catalyzed Amination: C N Bond Formation. 2022, 294-331. https://doi.org/10.1016/B978-0-12-820206-7.00091-3
    60. Yuliya O. Kuchkovska, Oleksandr O. Grygorenko. Azepines and Their Fused-Ring Derivatives. 2022, 1-93. https://doi.org/10.1016/B978-0-12-818655-8.00073-1
    61. Liuyang Deng, Ranran Guo, Lianjie Wang, Cao Yang, Zechao Wang. Rapid Construction of Acridines Via Bf3•Et2o Promoted Cyclization of 2−Phenylamino Benzophenones. SSRN Electronic Journal 2022, 53 https://doi.org/10.2139/ssrn.4133493
    62. Ghabi Amira, Souissi Salma, Gabsi Wahiba, Boubaker Taoufik. Nucleophilicities of para‐substituted aniline radical cations in acetonitrile: Kinetic investigation and structure–reactivity relationships. International Journal of Chemical Kinetics 2021, 53 (12) , 1262-1271. https://doi.org/10.1002/kin.21531
    63. Teng Liu, Yuqi Fang, Linhong Zuo, Yulian Yang, Yin Liu, Weipeng Chen, Li Dang, Wusheng Guo. Pd/LA-catalyzed decarboxylation enabled exclusive [5 + 2] annulation toward N -aryl azepanes and DFT insights. Organic Chemistry Frontiers 2021, 8 (9) , 1902-1909. https://doi.org/10.1039/D1QO00070E
    64. Francisco Garnes-Portolés, Rossella Greco, Judit Oliver-Meseguer, Jorge Castellanos-Soriano, M. Consuelo Jiménez, Miguel López-Haro, Juan Carlos Hernández-Garrido, Mercedes Boronat, Raúl Pérez-Ruiz, Antonio Leyva-Pérez. Regioirregular and catalytic Mizoroki–Heck reactions. Nature Catalysis 2021, 4 (4) , 293-303. https://doi.org/10.1038/s41929-021-00592-3
    65. Manvinder Kaur, Sonali Garg, Dharambeer S. Malhi, Harvinder S. Sohal. A Review on Synthesis, Reactions and Biological Properties of Seven Membered Heterocyclic Compounds: Azepine, Azepane, Azepinone. Current Organic Chemistry 2021, 25 (4) , 449-506. https://doi.org/10.2174/1385272825999210104222338
    66. Jingran Zhang, Xiaoxian Li, Xuemin Li, Haofeng Shi, Fengxia Sun, Yunfei Du. DMSO/SOCl 2 -mediated C(sp 2 )–H amination: switchable synthesis of 3-unsubstituted indole and 3-methylthioindole derivatives. Chemical Communications 2021, 57 (4) , 460-463. https://doi.org/10.1039/D0CC07453E
    67. Najeh Tka, Mohamed Adnene Hadj Ayed, Mourad Ben Braiek, Mahjoub Jabli, Noureddine Chaaben, Kamel Alimi, Stefan Jopp, Peter Langer. 2,4-Bis(arylethynyl)-9-chloro-5,6,7,8-tetrahydroacridines: synthesis and photophysical properties. Beilstein Journal of Organic Chemistry 2021, 17 , 1629-1640. https://doi.org/10.3762/bjoc.17.115
    68. Sarah Zeghada, Ghenia Bentabed-Ababsa, Olivier Mongin, William Erb, Laurent Picot, Valérie Thiéry, Thierry Roisnel, Vincent Dorcet, Florence Mongin. 2-Aminobenzaldehyde, a common precursor to acridines and acridones endowed with bioactivities. Tetrahedron 2020, 76 (38) , 131435. https://doi.org/10.1016/j.tet.2020.131435
    69. Viktor A. Zapol’skii, Ursula Bilitewski, Sören R. Kupiec, Isabell Ramming, Dieter E. Kaufmann. Polyhalonitrobutadienes as Versatile Building Blocks for the Biotargeted Synthesis of Substituted N-Heterocyclic Compounds. Molecules 2020, 25 (12) , 2863. https://doi.org/10.3390/molecules25122863
    70. Susanta Mandal, Karan Chhetri, Samuzal Bhuyan, Biswajit G. Roy. Efficient iron catalyzed ligand-free access to acridines and acridinium ions. Green Chemistry 2020, 22 (10) , 3178-3185. https://doi.org/10.1039/D0GC00617C
    71. Ha-Jeong Song, Eunyoung Yoon, Jung-Nyoung Heo. Efficient synthesis of dibenzazepine lactams via a sequential Pd-catalyzed amination and aldol condensation reaction. Tetrahedron Letters 2020, 61 (9) , 151536. https://doi.org/10.1016/j.tetlet.2019.151536
    72. Pietro Capurro, Andrea Basso. Chemical reactions for building small molecules. 2020, 35-82. https://doi.org/10.1016/B978-0-12-818349-6.00002-9
    73. A.S.G. Prasad, T. Bhaskara Rao, D. Rambabu, M.V. Basaveswara Rao, Manojit Pal. Ultrasound assisted Mizoroki–Heck coupling/C–H amination in a single pot: Direct synthesis of indole derivatives. Arabian Journal of Chemistry 2019, 12 (8) , 4320-4330. https://doi.org/10.1016/j.arabjc.2016.06.004
    74. Oleg N. Chupakhin, Alexander V. Shchepochkin, Valery N. Charushin, Anna V. Maiorova, Tatyana V. Kulikova, Konstantin Yu. Shunyaev, Andrey N. Enyashin, Pavel A. Slepukhin, Anna I. Suvorova. Electrochemical Oxidative Aromatizationof 9-Substituted 9,10-Dihydroacridines: Cleavage of C–H vs C–X Bond. Chemistry of Heterocyclic Compounds 2019, 55 (10) , 956-963. https://doi.org/10.1007/s10593-019-02562-x
    75. Carmen Nájera, Irina P. Beletskaya, Miguel Yus. Metal-catalyzed regiodivergent organic reactions. Chemical Society Reviews 2019, 48 (16) , 4515-4618. https://doi.org/10.1039/C8CS00872H
    76. Aminur Khan, Rejaul Karim, Hamid Dhimane, Safiul Alam. Mild and Efficient Synthesis of Functionalized Carbazoles via a DBU‐Assisted Sequence Involving Cu‐ and Pd‐Catalyzed Coupling Reactions. ChemistrySelect 2019, 4 (21) , 6598-6605. https://doi.org/10.1002/slct.201900788
    77. Vishnu Ji Ram, Arun Sethi, Mahendra Nath, Ramendra Pratap. Seven-Membered Heterocycles. 2019, 393-425. https://doi.org/10.1016/B978-0-12-819210-8.00003-5
    78. Kristen Berger, Grant McCormick, Joseph Jaye, Christina Rozeske, Eric Fort. Synthesis of Acridines through Alkyne Addition to Diarylamines. Molecules 2018, 23 (11) , 2867. https://doi.org/10.3390/molecules23112867
    79. Alessandra Casnati, Marco Fontana, Giovanni Coruzzi, Brunella Maria Aresta, Nicola Corriero, Raimondo Maggi, Giovanni Maestri, Elena Motti, Nicola Della Ca'. Enhancing Reactivity and Selectivity of Aryl Bromides: A Complementary Approach to Dibenzo[ b,f ]azepine Derivatives. ChemCatChem 2018, 10 (19) , 4346-4352. https://doi.org/10.1002/cctc.201800940
    80. Jayanta Ghorai, Angula Chandra Shekar Reddy, Pazhamalai Anbarasan. Divergent Functionalization of N ‐Alkyl‐2‐alkenylanilines: Efficient Synthesis of Substituted Indoles and Quinolines. Chemistry – An Asian Journal 2018, 13 (17) , 2499-2504. https://doi.org/10.1002/asia.201800441
    81. Yen‐Chun Lee, Kamal Kumar, Herbert Waldmann. Ligand‐Directed Divergent Synthesis of Carbo‐ and Heterocyclic Ring Systems. Angewandte Chemie International Edition 2018, 57 (19) , 5212-5226. https://doi.org/10.1002/anie.201710247
    82. Yen‐Chun Lee, Kamal Kumar, Herbert Waldmann. Ligandengesteuerte divergente Synthese von carbo‐ und heterocyclischen Ringsystemen. Angewandte Chemie 2018, 130 (19) , 5308-5322. https://doi.org/10.1002/ange.201710247
    83. Yuki Kanase, Takafumi Kitada, Hidetsugu Tabata, Kosho Makino, Tetsuta Oshitari, Hiromi Ohashi, Takashi Yoshinaga, Hideaki Natsugari, Hideyo Takahashi. 4-Substituted carbamazepine derivatives: Conformational analysis and sodium channel-blocking properties. Bioorganic & Medicinal Chemistry 2018, 26 (9) , 2508-2513. https://doi.org/10.1016/j.bmc.2018.04.013
    84. Wenjing Li, Yongjun Gao, Pei Tang, Yao Xu, Ding Ma. One-step synthesis of carbon-supported copper nanoparticles from biomass for N-arylation of pyrazole. Journal of Energy Chemistry 2018, 27 (3) , 859-865. https://doi.org/10.1016/j.jechem.2017.06.003
    85. Nahida Mokhtari Brikci-Nigassa, Ghenia Bentabed-Ababsa, William Erb, Floris Chevallier, Laurent Picot, Lucille Vitek, Audrey Fleury, Valérie Thiéry, Mohamed Souab, Thomas Robert, Sandrine Ruchaud, Stéphane Bach, Thierry Roisnel, Florence Mongin. 2-Aminophenones, a common precursor to N-aryl isatins and acridines endowed with bioactivities. Tetrahedron 2018, 74 (15) , 1785-1801. https://doi.org/10.1016/j.tet.2018.02.038
    86. Lina M. Acosta Quintero, Isidro Burgos, Alirio Palma, Justo Cobo, Christopher Glidewell. A concise, efficient and versatile synthesis of amino-substituted benzo[ b ]pyrimido[5,4- f ]azepines: synthesis and spectroscopic characterization, together with the molecular and supramolecular structures of three products and one intermediate. Acta Crystallographica Section C Structural Chemistry 2018, 74 (3) , 312-320. https://doi.org/10.1107/S2053229618002176
    87. Daniel Solé, Israel Fernández. Controlling Selectivities in Palladium-Catalyzed Cyclization Reactions Leading to Heterocycles. 2018, 311-337. https://doi.org/10.1016/B978-0-12-811651-7.00008-X
    88. Botla Vinayak, Pardhi Vishal Ravindrakumar, Daggupati V. Ramana, Malapaka Chandrasekharam. Revisiting 1-chloro-1,2-benziodoxol-3-one: efficient ortho -chlorination of aryls under aqueous conditions. New Journal of Chemistry 2018, 42 (11) , 8953-8959. https://doi.org/10.1039/C8NJ00530C
    89. Wan‐Lu Mu, Meirong Wang, Hui‐Jing Li, Deng‐Ming Huang, Yi‐Yun Zhang, Chao‐Yi Li, Ying Liu, Yan‐Chao Wu. Palladium‐Catalyzed Regioselective Oxidative Annulation of Cyclohexanones and 2‐Aminophenyl Ketones Using Molecular Oxygen as the Sole Oxidant. Advanced Synthesis & Catalysis 2017, 359 (23) , 4250-4257. https://doi.org/10.1002/adsc.201700715
    90. Zhanhui Yang, Shiyi Yang, Muhammad Sohail Haroone, Wei He, Jiaxi Xu. Sulfur-mediated C(sp 2 )–H imidation and 1,2-imidofluorination of vinyl sulfides. Tetrahedron 2017, 73 (24) , 3338-3346. https://doi.org/10.1016/j.tet.2017.04.057
    91. John P. Wolfe, David W. Old, Sikervar Vikas, Pabba Jagadish, Dasgupta Mayukh. 2-Dicyclohexylphosphino-2′-( N , N -dimethylamino)biphenyl. 2017, 1-13. https://doi.org/10.1002/047084289X.rn00133.pub3
    92. Tse‐Lok Ho, Mary Fieser, Louis Fieser. Tris(dibenzylideneacetone)dipalladium. 2017https://doi.org/10.1002/9780471264194.fos11451.pub5
    93. Tse‐Lok Ho, Mary Fieser, Louis Fieser. Tris(dibenzylideneacetone)dipalladium. 2017https://doi.org/10.1002/9780471264194.fos11451.pub6
    94. Xiangui Chen, Yanjun Xie, Cheng Li, Fuhong Xiao, Guo‐Jun Deng. Synthesis of Substituted Acridines through a Palladium‐Catalyzed Condensation/Cyclization/Tautomerization Sequence. European Journal of Organic Chemistry 2017, 2017 (3) , 577-581. https://doi.org/10.1002/ejoc.201601553
    95. Jan Ježek, Jan Hlaváček, Jaroslav Šebestík. Syntheses. 2017, 9-45. https://doi.org/10.1007/978-3-319-63953-6_3
    96. Bo Cao, Marwan Simaan, Ilan Marek, Yin Wei, Min Shi. Palladium-catalyzed oxidative cyclization of aniline-tethered alkylidenecyclopropanes with O 2 : a facile protocol to selectively synthesize 2- and 3-vinylindoles. Chemical Communications 2017, 53 (1) , 216-219. https://doi.org/10.1039/C6CC08731K
    97. Soumitra Agasti, Aniruddha Dey, Debabrata Maiti. Palladium-catalyzed benzofuran and indole synthesis by multiple C–H functionalizations. Chemical Communications 2017, 53 (49) , 6544-6556. https://doi.org/10.1039/C7CC02053H
    98. Rui Wang, Ruo-Xing Jin, Zi-Yang Qin, Kang-Jie Bian, Xi-Sheng Wang. Novel and facile synthesis of 1-benzazepines via copper-catalyzed oxidative C(sp 3 )–H/C(sp 2 )–H cross-coupling. Chemical Communications 2017, 53 (90) , 12229-12232. https://doi.org/10.1039/C7CC07027F
    99. Wubing Yao, Bin Zhang, Rongrong Li, Huajiang Jiang, Xiaoying Chen, Fang Li. A general and mild Cu-catalytic N-arylation of iminodibenzyls and iminostilbenes using unactivated aryl halides. RSC Adv. 2017, 7 (78) , 49600-49604. https://doi.org/10.1039/C7RA07437A
    100. Tanu Gupta, Jay Bahadur Singh, Kalpana Mishra, Radhey M. Singh. Active methylene compounds (AMCs) controlled facile synthesis of acridine and phenanthridine from morita Baylis–Hillman acetate. RSC Advances 2017, 7 (86) , 54581-54585. https://doi.org/10.1039/C7RA09447G
    Load all citations
    Download PDF

    Pair your accounts.

    Export articles to Mendeley

    Get article recommendations from ACS based on references in your Mendeley library.

    Pair your accounts.

    Export articles to Mendeley

    Get article recommendations from ACS based on references in your Mendeley library.

    You’ve supercharged your research process with ACS and Mendeley!

    STEP 1:
    Click to create an ACS ID

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    MENDELEY PAIRING EXPIRED
    Your Mendeley pairing has expired. Please reconnect