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Palladium-Catalyzed Intermolecular Aerobic Oxidative Cyclization of 2-Ethynylanilines with Isocyanides: Regioselective Synthesis of 4-Halo-2-aminoquinolines

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School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou, Guangdong 510640, PR China
*E-mail: [email protected]
Cite this: J. Org. Chem. 2013, 78, 20, 10319–10328
Publication Date (Web):September 23, 2013
https://doi.org/10.1021/jo401707j
Copyright © 2013 American Chemical Society
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    Abstract

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    A robust and regioselective palladium-catalyzed intermolecular aerobic oxidative cyclization of 2-ethynylanilines with isocyanides to the synthesis of 4-halo-2-aminoquinolines is reported herein. The procedure constructs various 4-halo-2-aminoquinolines with moderate to excellent yields (47–94%) and broad substrates scope. Furthermore, this process can be easily extended to synthesis of various 6H-indolo[2,3-b]quinolines via an intramolecular Buchwald–Hartwig cross-coupling reaction in two-step one-pot manner.

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    2. Meng Li, Jia Zheng, Weigao Hu, Chunsheng Li, Jianxiao Li, Songjia Fang, Huanfeng Jiang, Wanqing Wu. Palladium-Catalyzed Cyclization of N-Acyl-o-alkynylanilines with Isocyanides Involving a 1,3-Acyl Migration: Rapid Access to Functionalized 2-Aminoquinolines. Organic Letters 2018, 20 (22) , 7245-7248. https://doi.org/10.1021/acs.orglett.8b03165
    3. Weigao Hu, Meng Li, Guangbin Jiang, Wanqing Wu, Huanfeng Jiang. Synthesis of 2,3-Difunctionalized Benzofuran Derivatives through Palladium-Catalyzed Double Isocyanide Insertion Reaction. Organic Letters 2018, 20 (12) , 3500-3503. https://doi.org/10.1021/acs.orglett.8b01277
    4. Yongjie Yang, ChengCheng Fei, Kai Wang, Bo Liu, Dingxin Jiang, Biaolin Yin. Access to Densely Functionalized Chalcone Derivatives with a 2-Pyridone Subunit via Pd/Cu-Catalyzed Oxidative Furan–Yne Cyclization of N-(2-Furanylmethyl) Alkynamides under Air. Organic Letters 2018, 20 (8) , 2273-2277. https://doi.org/10.1021/acs.orglett.8b00618
    5. Thangavel Selvi, Sivan Velmathi. Indium(III) Triflate-Catalyzed Reactions of Aza-Michael Adducts of Chalcones with Aromatic Amines: Retro-Michael Addition versus Quinoline Formation. The Journal of Organic Chemistry 2018, 83 (7) , 4087-4091. https://doi.org/10.1021/acs.joc.7b03151
    6. Teppei Sasaki, Katsuhiko Moriyama, and Hideo Togo . Preparation of 3-Iodoquinolines from N-Tosyl-2-propynylamines with Diaryliodonium Triflate and N-Iodosuccinimide. The Journal of Organic Chemistry 2017, 82 (22) , 11727-11734. https://doi.org/10.1021/acs.joc.7b01433
    7. Jianwen Peng, Yang Gao, Chuanle Zhu, Bifu Liu, Yinglan Gao, Miao Hu, Wanqing Wu, and Huanfeng Jiang . Synthesis of Polysubstituted 3-Amino Pyrroles via Palladium-Catalyzed Multicomponent Reaction. The Journal of Organic Chemistry 2017, 82 (7) , 3581-3588. https://doi.org/10.1021/acs.joc.7b00098
    8. Weigao Hu, Jiawei Li, Yanli Xu, Jianxiao Li, Wanqing Wu, Haiyang Liu, and Huanfeng Jiang . Palladium-Catalyzed Redox-Neutral N–O/C(sp3)–H Functionalization of Aryl Oximes with Isocyanides. Organic Letters 2017, 19 (3) , 678-681. https://doi.org/10.1021/acs.orglett.6b03852
    9. Ling Fan, Meilin Liu, Yu Ye, and Guodong Yin . Synthesis of 6-Substituted 6H-Indolo[2,3-b]quinolines from Isoindigos. Organic Letters 2017, 19 (1) , 186-189. https://doi.org/10.1021/acs.orglett.6b03484
    10. Weigao Hu, Jia Zheng, Jianxiao Li, Bifu Liu, Wanqing Wu, Haiyang Liu, and Huanfeng Jiang . Assembly of Polysubstituted Maleimides via Palladium-Catalyzed Cyclization Reaction of Alkynes with Isocyanides. The Journal of Organic Chemistry 2016, 81 (24) , 12451-12458. https://doi.org/10.1021/acs.joc.6b02227
    11. Jianwen Peng, Yang Gao, Weigao Hu, Yinglan Gao, Miao Hu, Wanqing Wu, Yanwei Ren, and Huanfeng Jiang . Palladium-Catalyzed Multicomponent Reaction (MCR) of Propargylic Carbonates with Isocyanides. Organic Letters 2016, 18 (22) , 5924-5927. https://doi.org/10.1021/acs.orglett.6b02999
    12. Christine M. Le, Theresa Sperger, Rui Fu, Xiao Hou, Yong Hwan Lim, Franziska Schoenebeck, and Mark Lautens . Stereoselective Synthesis of Methylene Oxindoles via Palladium(II)-Catalyzed Intramolecular Cross-Coupling of Carbamoyl Chlorides. Journal of the American Chemical Society 2016, 138 (43) , 14441-14448. https://doi.org/10.1021/jacs.6b08925
    13. 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
    14. James D. Neuhaus, Sarah M. Morrow, Michael Brunavs, and Michael C. Willis . Diversely Substituted Quinolines via Rhodium-Catalyzed Alkyne Hydroacylation. Organic Letters 2016, 18 (7) , 1562-1565. https://doi.org/10.1021/acs.orglett.6b00390
    15. Yuan-Yuan Pan, Ya-Nan Wu, Zhen-Zhen Chen, Wen-Juan Hao, Guigen Li, Shu-Jiang Tu, and Bo Jiang . Synthesis of 3-Iminoindol-2-amines and Cyclic Enaminones via Palladium-Catalyzed Isocyanide Insertion-Cyclization. The Journal of Organic Chemistry 2015, 80 (11) , 5764-5770. https://doi.org/10.1021/acs.joc.5b00727
    16. Yalla Kiran Kumar, Gadi Ranjith Kumar, Thota Jagadeshwar Reddy, Balasubramanian Sridhar, and Maddi Sridhar Reddy . Synthesis of 3-Sulfonylamino Quinolines from 1-(2-Aminophenyl) Propargyl Alcohols through a Ag(I)-Catalyzed Hydroamination, (2 + 3) Cycloaddition, and an Unusual Strain-Driven Ring Expansion. Organic Letters 2015, 17 (9) , 2226-2229. https://doi.org/10.1021/acs.orglett.5b00832
    17. Mohammad Rehan, Gurupada Hazra, and Prasanta Ghorai . Synthesis of Polysubstituted Quinolines via Transition-Metal-Free Oxidative Cycloisomerization of o-Cinnamylanilines. Organic Letters 2015, 17 (7) , 1668-1671. https://doi.org/10.1021/acs.orglett.5b00419
    18. Zhenming Zhang, Lu Ouyang, Wanqing Wu, Jianxiao Li, Zhicai Zhang, and Huanfeng Jiang . Palladium-Catalyzed Intermolecular Oxyvinylcyclization of Alkenes with Alkynes: An Approach to 3-Methylene γ-Lactones and Tetrahydrofurans. The Journal of Organic Chemistry 2014, 79 (22) , 10734-10742. https://doi.org/10.1021/jo501606c
    19. Xiaochen Ji, Huawen Huang, Wenfang Xiong, Kunbo Huang, Wanqing Wu, and Huanfeng Jiang . Palladium-Catalyzed Oxidative C–N Bond Coupling Involving a Solvent-Controlled Regioselective Bromination Process. The Journal of Organic Chemistry 2014, 79 (15) , 7005-7011. https://doi.org/10.1021/jo501171c
    20. Nuligonda Thirupathi, Madala Hari Babu, Vikas Dwivedi, Ruchir Kant, and Maddi Sridhar Reddy . Palladium-Catalyzed Tandem Intramolecular Oxy/Amino-Palladation/Isocyanide Insertion: Synthesis of α-Benzofuranyl/Indolylacetamides. Organic Letters 2014, 16 (11) , 2908-2911. https://doi.org/10.1021/ol501048x
    21. Ahanthem Priyanca Devi, Keshav Lalit Ameta, Andrea Penoni, Vnira R. Akhmetova, Rajendra P. Pawar, Is Fatimah. An Overview of Palladium-Catalyzed Fabrication of Some Heterocyclic Frameworks. Mini-Reviews in Organic Chemistry 2023, 20 (5) , 455-482. https://doi.org/10.2174/1570193X19666220615095645
    22. Rana Chatterjee, Mohanreddy Pothireddy, Rambabu Dandela. Copper-Catalyzed Decarboxylative Cascade Cyclization for the Synthesis of 2-Arylquinolines. Synlett 2023, 34 (09) , 1058-1062. https://doi.org/10.1055/a-1990-3283
    23. Qiongwen Kang, Mengdan Wang, Zongkang Wang, Lu Cheng, Yilin Zhu, Chengyu Wang, Yanzhong Li. Base-promoted selective C2–N1 ring-expansion reaction of indolones toward substituted quinolines. Organic Chemistry Frontiers 2023, 22 https://doi.org/10.1039/D3QO00818E
    24. Meng Li, Ruixue Zhang, Qiushan Gao, Huanfeng Jiang, Ming Lei, Wanqing Wu. Divergent Synthesis of Fused Tetracyclic Heterocycles from Diarylalkynes Enabled by the Selective Insertion of Isocyanide. Angewandte Chemie International Edition 2022, 61 (42) https://doi.org/10.1002/anie.202208203
    25. Meng Li, Ruixue Zhang, Qiushan Gao, Huanfeng Jiang, Ming Lei, Wanqing Wu. Divergent Synthesis of Fused Tetracyclic Heterocycles from Diarylalkynes Enabled by the Selective Insertion of Isocyanide. Angewandte Chemie 2022, 134 (42) https://doi.org/10.1002/ange.202208203
    26. Ben‐Jie Jiang, Song‐Lin Zhang. Synthesis of Quinolines and 2‐Functionalized Quinolines by Difluorocarbene Incorporation. Advanced Synthesis & Catalysis 2022, 364 (13) , 2157-2162. https://doi.org/10.1002/adsc.202200263
    27. Vivek Kumar Singh, S. N. R. Donthireddy, Vipin K. Pandey, Arnab Rit. Ru II -Complexes of heteroditopic chelating NHC ligands: effective catalysts for the β-alkylation of secondary alcohols and the synthesis of 2-alkylaminoquinoline derivatives following the dehydrogenative protocol. Organic & Biomolecular Chemistry 2022, 20 (9) , 1945-1951. https://doi.org/10.1039/D2OB00034B
    28. Qiushan Gao, Meng Li, Wanqing Wu. Recent Advances in Transition Metal-Catalyzed Isocyanide Insertion Reactions. Chinese Journal of Organic Chemistry 2022, 42 (9) , 2659. https://doi.org/10.6023/cjoc202204007
    29. Haruyasu Asahara, Yusuke Mukaijo, Kengo Muragishi, Kento Iwai, Akitaka Ito, Nagatoshi Nishiwaki. Metal‐Free and syn ‐Selective Hydrohalogenation of Alkynes through a Pseudo‐Intramolecular Process. European Journal of Organic Chemistry 2021, 2021 (42) , 5747-5755. https://doi.org/10.1002/ejoc.202101134
    30. Balaji Ganesan, Karthick Govindan, Gopal Chandru Senadi, Mohanraj Kandasamy, Wei-Yu Lin. Copper-catalyzed synthesis of aminoquinolines from β-(2-aminophenyl)-α,β-ynones using DMF as dual synthon. Chemical Communications 2020, 56 (48) , 6488-6491. https://doi.org/10.1039/D0CC03033C
    31. Pradip Debnath. Recent Advances in the Hofmann Rearrangement and Its Application to Natural Product Synthesis. Current Organic Chemistry 2020, 23 (22) , 2402-2435. https://doi.org/10.2174/1385272823666191021115508
    32. Chieh-Kai Chan, Chien-Yu Lai, Wei-Chih Lo, Yu-Ting Cheng, Meng-Yang Chang, Cheng-Chung Wang. p -TsOH-mediated synthesis of substituted 2,4-diaryl-3-sulfonylquinolines from functionalized 2-aminobenzophenones and aromatic β-ketosulfones under microwave irradiation. Organic & Biomolecular Chemistry 2020, 18 (2) , 305-315. https://doi.org/10.1039/C9OB02445J
    33. José Sebastião Santos Neto, Gilson Zeni. Ten years of progress in the synthesis of six-membered N-heterocycles from alkynes and nitrogen sources. Tetrahedron 2020, 76 (4) , 130876. https://doi.org/10.1016/j.tet.2019.130876
    34. Lu Ouyang, Wanqing Wu, Huanfeng Jiang. Green Oxidative Synthesis of Ethers, Esters, and Organic Halides. 2019, 79-121. https://doi.org/10.1002/9781119304197.ch3
    35. Yu-Zhao Wang, Heng-Rui Zhang, Li Zhou, Jun-Dan Fang, Xue-Yuan Liu. Photoredox-catalyzed sulfenylation/cyclization of N-aryl-N-tosylpropargylamine with disulfide: A concise route to 3-phenylthioquinoline. Tetrahedron 2019, 75 (20) , 2893-2899. https://doi.org/10.1016/j.tet.2019.04.017
    36. Nagaraju Marepu, Mahesh Gosi, Santhoshi Sumana Vedula, Sunandamma Yeturu, Manojit Pal. Ultrasound-assisted Synthesis of 6-substituted indolo[2,3-b]quinolines: their Evaluation as Potential Cytotoxic Agents. Mini-Reviews in Medicinal Chemistry 2019, 19 (7) , 599-608. https://doi.org/10.2174/1389557518666180727170055
    37. Vladimir V. Kouznetsov, Carlos M. Meléndez Gómez, José Luis Valencia Peña, Leonor Y. Vargas-Méndez. Natural and synthetic quinoline molecules against tropical parasitic pathologies: an analysis of activity and structural evolution for developing new quinoline-based antiprotozoal agents. 2019, 87-164. https://doi.org/10.1016/B978-0-12-815723-7.00004-3
    38. Jun‐Ho Choi, Cheol‐Min Park. Three‐Component Synthesis of Quinolines Based on Radical Cascade Visible‐Light Photoredox Catalysis. Advanced Synthesis & Catalysis 2018, 360 (18) , 3553-3562. https://doi.org/10.1002/adsc.201800734
    39. Weigao Hu, Jia Zheng, Meng Li, Wanqing Wu, Haiyang Liu, Huanfeng Jiang. Palladium‐Catalyzed Intermolecular Oxidative Coupling Reactions of ( Z )‐Enamines with Isocyanides through Selective β‐C(sp 2 )‐H and/or C=C Bond Cleavage. Chinese Journal of Chemistry 2018, 36 (8) , 712-715. https://doi.org/10.1002/cjoc.201800127
    40. Rashmi Sharma, Parteek Kour, Anil Kumar. A review on transition-metal mediated synthesis of quinolines. Journal of Chemical Sciences 2018, 130 (6) https://doi.org/10.1007/s12039-018-1466-8
    41. Kyohei Yonekura, Mika Shinoda, Yuko Yonekura, Teruhisa Tsuchimoto. Indium-Catalyzed Annulation of o-Acylanilines with Alkoxyheteroarenes: Synthesis of Heteroaryl[b]quinolines and Subsequent Transformation to Cryptolepine Derivatives. Molecules 2018, 23 (4) , 838. https://doi.org/10.3390/molecules23040838
    42. Ghazwan Ali Salman, Sophie Janke, Ngo Nghia Pham, Peter Ehlers, Peter Langer. Convenient synthesis of 10 H -indolo[3,2- b ]quinolines and 6 H -indolo[2,3- b ]quinolines by sequential chemoselective Suzuki reaction followed by double C-N coupling. Tetrahedron 2018, 74 (10) , 1024-1032. https://doi.org/10.1016/j.tet.2018.01.010
    43. Vijai K. Rai, Fooleswar Verma, Ganeshwar P. Sahu, Manorama Singh, Ankita Rai. One‐Pot Allan–Robinson/Friedländer Route to Chromen‐/Quinolin‐4‐ones through the Domino Acetylative Cyclisation of 2‐Hydroxy‐/2‐Aminobenzaldehydes. European Journal of Organic Chemistry 2018, 2018 (4) , 537-544. https://doi.org/10.1002/ejoc.201701435
    44. Zineb Imene Dehimat, Sedat Yaşar, Dahmane Tebbani, İsmail Özdemir. Sonogashira cross-coupling reaction catalyzed by N-heterocyclic carbene-Pd(II)-PPh3 complexes under copper free and aerobic conditions. Inorganica Chimica Acta 2018, 469 , 325-334. https://doi.org/10.1016/j.ica.2017.09.048
    45. Deli Sun, Kun Yin, Ronghua Zhang. Visible-light-induced multicomponent cascade cycloaddition involving N -propargyl aromatic amines, diaryliodonium salts and sulfur dioxide: rapid access to 3-arylsulfonylquinolines. Chemical Communications 2018, 54 (11) , 1335-1338. https://doi.org/10.1039/C7CC09410H
    46. He Zhao, Xiuwen Chen, Huanfeng Jiang, Min Zhang. Copper-catalysed dehydrogenative α-C(sp 3 )–H amination of tetrahydroquinolines with O -benzoyl hydroxylamines. Organic Chemistry Frontiers 2018, 5 (4) , 539-543. https://doi.org/10.1039/C7QO00794A
    47. Xi Zhang, Tong-Lin Wang, Cong-De Huo, Xi-Cun Wang, Zheng-Jun Quan. Base-controlled chemoselectivity reaction of vinylanilines with isothiocyanates for synthesis of quinolino-2-thione and 2-aminoquinoline derivatives. Chemical Communications 2018, 54 (25) , 3114-3117. https://doi.org/10.1039/C8CC00062J
    48. Wanqing Wu, Meng Li, Jia Zheng, Weigao Hu, Chunsheng Li, Huanfeng Jiang. Tandem cyclization of o -alkynylanilines with isocyanides triggered by intramolecular nucleopalladation: access to heterocyclic fused 2-aminoquinolines. Chemical Communications 2018, 54 (50) , 6855-6858. https://doi.org/10.1039/C8CC02028K
    49. Jiwei Wu, Zhixiong Liao, Dong Liu, Chien‐Wei Chiang, Zheng Li, Zhonghao Zhou, Hong Yi, Xu Zhang, Zixin Deng, Aiwen Lei. From Anilines to Quinolines: Iodide‐ and Silver‐Mediated Aerobic Double C−H Oxidative Annulation–Aromatization. Chemistry – A European Journal 2017, 23 (63) , 15874-15878. https://doi.org/10.1002/chem.201703218
    50. Weigao Hu, Zun Li, Jiawei Li, Wanqing Wu, Haiyang Liu, Huanfeng Jiang. Palladium‐Catalyzed Cross‐Coupling of Alkynyl Carboxylic Acids with Isocyanides: Solvent‐Controlled Selective Synthesis of 5‐Iminofuranones and 5‐Iminopyrrolones. Advanced Synthesis & Catalysis 2017, 359 (20) , 3509-3514. https://doi.org/10.1002/adsc.201700533
    51. S.S. Devkule, S.S. Chavan. Copper(I) complexes of N-(2-quinolynylmethylene)-1H-benzimidazole and triphenylphosphine: Synthesis, characterization, luminescence and catalytic properties. Inorganica Chimica Acta 2017, 466 , 122-129. https://doi.org/10.1016/j.ica.2017.05.076
    52. Anindita Dewan, Manashi Sarmah, Utpal Bora, Ashim J. Thakur. In situ generation of palladium nanoparticles using agro waste and their use as catalyst for copper-, amine- and ligand-free Sonogashira reaction. Applied Organometallic Chemistry 2017, 31 (7) , e3646. https://doi.org/10.1002/aoc.3646
    53. Wan Lv, Biao Xiong, Huanfeng Jiang, Min Zhang. Synthesis of 2-Alkylaminoquinolines and 1,8-Naphthyridines by Successive Ruthenium-Catalyzed Dehydrogenative Annulation and N -Alkylation Processes. Advanced Synthesis & Catalysis 2017, 359 (7) , 1202-1207. https://doi.org/10.1002/adsc.201601287
    54. Morteza Shiri, Maryam Ranjbar, Zahra Yasaei, Fatemeh Zamanian, Behrouz Notash. Palladium-catalyzed tandem reaction of 2-chloroquinoline-3-carbaldehydes and isocyanides. Organic & Biomolecular Chemistry 2017, 15 (47) , 10073-10081. https://doi.org/10.1039/C7OB02043K
    55. Zun Li, Jia Zheng, Weigao Hu, Jianxiao Li, Wanqing Wu, Huanfeng Jiang. Synthesis of 1,4-enyne-3-ones via palladium-catalyzed sequential decarboxylation and carbonylation of allyl alkynoates. Organic Chemistry Frontiers 2017, 4 (7) , 1363-1366. https://doi.org/10.1039/C7QO00082K
    56. Hongming Jin, Bin Tian, Xinlong Song, Jin Xie, Matthias Rudolph, Frank Rominger, A. Stephen K. Hashmi. Gold‐Catalyzed Synthesis of Quinolines from Propargyl Silyl Ethers and Anthranils through the Umpolung of a Gold Carbene Carbon. Angewandte Chemie International Edition 2016, 55 (41) , 12688-12692. https://doi.org/10.1002/anie.201606043
    57. Hongming Jin, Bin Tian, Xinlong Song, Jin Xie, Matthias Rudolph, Frank Rominger, A. Stephen K. Hashmi. Gold‐katalysierte Synthese von Chinolinen aus Propargylsilylethern und Anthranilen über die Umpolung eines Goldcarben‐Kohlenstoffatoms. Angewandte Chemie 2016, 128 (41) , 12880-12884. https://doi.org/10.1002/ange.201606043
    58. Anindita Dewan, Manashi Sarmah, Utpal Bora, Ashim J. Thakur. A green protocol for ligand, copper and base free Sonogashira cross-coupling reaction. Tetrahedron Letters 2016, 57 (33) , 3760-3763. https://doi.org/10.1016/j.tetlet.2016.07.021
    59. Xinxing Gong, Mo Chen, Liangqing Yao, Jie Wu. Facile Assembly of Benzo[ b ]naphtho[2,3‐ d ]azocin‐6(5  H )‐ones by a Palladium‐Catalyzed Double Carbometalation. Chemistry – An Asian Journal 2016, 11 (10) , 1613-1617. https://doi.org/10.1002/asia.201600211
    60. Qiang Zheng, Qiuping Ding, Cong Wang, Wenfan Chen, Yiyuan Peng. Synthesis of 2-aminoquinolines via palladium-catalyzed intermolecular oxidative cyclization of 2-vinylanilines with isocyanides. Tetrahedron 2016, 72 (7) , 952-958. https://doi.org/10.1016/j.tet.2015.12.060
    61. Nuligonda Thirupathi, Surendra Puri, Thota Jagadeshwar Reddy, Balasubramanian Sridhar, Maddi Sridhar Reddy. Palladium(II)‐Catalyzed Sequential Aminopalladation and Oxidative Coupling with Acetylenes/Enones: Synthesis of Newly Substituted Quinolines from 2‐Aminophenyl Propargyl Alcohols. Advanced Synthesis & Catalysis 2016, 358 (2) , 303-313. https://doi.org/10.1002/adsc.201500805
    62. Song-Lin Zhang, Zhu-Qin Deng. Synthesis of quinolines and naphthyridines via catalytic retro-aldol reaction of β-hydroxyketones with ortho-aminobenzaldehydes or nicotinaldehydes. Organic & Biomolecular Chemistry 2016, 14 (38) , 8966-8970. https://doi.org/10.1039/C6OB01452F
    63. Samahe Sadjadi, Majid M. Heravi, Niousha Nazari. Isocyanide-based multicomponent reactions in the synthesis of heterocycles. RSC Advances 2016, 6 (58) , 53203-53272. https://doi.org/10.1039/C6RA02143C
    64. Shiv Dhiman, Hitesh Kumar Saini, Nitesh Kumar Nandwana, Dalip Kumar, Anil Kumar. Copper-catalyzed synthesis of quinoline derivatives via tandem Knoevenagel condensation, amination and cyclization. RSC Advances 2016, 6 (29) , 23987-23994. https://doi.org/10.1039/C6RA03798D
    65. Peng Zhou, Weibing Liu, Huihua Qiu. Synthesis of Functionalized 3-Bromoindenes via Pd(II)-catalyzed Tandem Reactions of o -(Alkynyl)styrenes: Taking Dioxygen as Sole Oxidant. Chemistry Letters 2015, 44 (12) , 1637-1639. https://doi.org/10.1246/cl.150756
    66. Jianquan Liu, Zhenhua Liu, Peiqiu Liao, Lin Zhang, Tao Tu, Xihe Bi. Silver-Catalyzed Cross-Coupling of Isocyanides and Active Methylene Compounds by a Radical Process. Angewandte Chemie 2015, 127 (36) , 10764-10768. https://doi.org/10.1002/ange.201504254
    67. Jianquan Liu, Zhenhua Liu, Peiqiu Liao, Lin Zhang, Tao Tu, Xihe Bi. Silver-Catalyzed Cross-Coupling of Isocyanides and Active Methylene Compounds by a Radical Process. Angewandte Chemie International Edition 2015, 54 (36) , 10618-10622. https://doi.org/10.1002/anie.201504254
    68. Ouldouz Ghashghaei, Marc Revés, Nicola Kielland, Rodolfo Lavilla. Modular Access to Tetrasubstituted Imidazolium Salts through Acid-Catalyzed Addition of Isocyanides to Propargylamines. European Journal of Organic Chemistry 2015, 2015 (20) , 4383-4388. https://doi.org/10.1002/ejoc.201500502
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    71. Qian Gao, Peng Zhou, Feng Liu, Wen-Juan Hao, Changsheng Yao, Bo Jiang, Shu-Jiang Tu. Cobalt( ii )/silver relay catalytic isocyanide insertion/cycloaddition cascades: a new access to pyrrolo[2,3-b]indoles. Chemical Communications 2015, 51 (46) , 9519-9522. https://doi.org/10.1039/C5CC02754C
    72. Pieter Mampuys, Yanping Zhu, Tjøstil Vlaar, Eelco Ruijter, Romano V. A. Orru, Bert U. W. Maes. Sustainable Three-Component Synthesis of Isothioureas from Isocyanides, Thiosulfonates, and Amines. Angewandte Chemie 2014, 126 (47) , 13063-13068. https://doi.org/10.1002/ange.201406717
    73. Pieter Mampuys, Yanping Zhu, Tjøstil Vlaar, Eelco Ruijter, Romano V. A. Orru, Bert U. W. Maes. Sustainable Three-Component Synthesis of Isothioureas from Isocyanides, Thiosulfonates, and Amines. Angewandte Chemie International Edition 2014, 53 (47) , 12849-12854. https://doi.org/10.1002/anie.201406717
    74. Suravi Chakrabarty, Shruti Choudhary, Arpit Doshi, Fa-Qiang Liu, Rishabh Mohan, Manasa P. Ravindra, Dhruv Shah, Xun Yang, Fraser F. Fleming. Catalytic Isonitrile Insertions and Condensations Initiated by RNC-X Complexation. Advanced Synthesis & Catalysis 2014, 356 (10) , 2135-2196. https://doi.org/10.1002/adsc.201400017
    75. Tjøstil Vlaar, Lisa Bensch, Jasper Kraakman, Christophe M. L. Vande Velde, Bert U. W. Maes, Romano V. A. Orru, Eelco Ruijter. Synthesis of Diverse Azolo[ c ]quinazolines by Palladium(II)- Catalyzed Aerobic Oxidative Insertion of Isocyanides. Advanced Synthesis & Catalysis 2014, 356 (6) , 1205-1209. https://doi.org/10.1002/adsc.201301129
    76. Bifu Liu, Hanling Gao, Yue Yu, Wanqing Wu, Huanfeng Jiang. ChemInform Abstract: Palladium-Catalyzed Intermolecular Aerobic Oxidative Cyclization of 2-Ethynylanilines with Isocyanides: Regioselective Synthesis of 4-Halo-2-aminoquinolines.. ChemInform 2014, 45 (13) , no-no. https://doi.org/10.1002/chin.201413156
    77. Jia Zheng, Min Zhang, Liangbin Huang, Xiaohan Hu, Wanqing Wu, Huawen Huang, Huangfeng Jiang. Regioselective synthesis of oxazole derivatives via palladium-catalyzed and copper-mediated cascade oxidative cyclization. Chem. Commun. 2014, 50 (27) , 3609-3611. https://doi.org/10.1039/C3CC49788G
    78. Huanfeng Jiang, Hanling Gao, Bifu Liu, Wanqing Wu. Palladium-catalyzed selective aminoamidation and aminocyanation of alkenes using isonitrile as amide and cyanide sources. Chem. Commun. 2014, 50 (97) , 15348-15351. https://doi.org/10.1039/C4CC07743A
    79. Baishan Jiang, Langxi Hu, Weijun Gui. Facile synthesis of 2-amino-3-bromoquinolines by palladium-catalyzed isocyanide insertion and cyclization of gem-dibromovinylanilines. RSC Adv. 2014, 4 (27) , 13850-13853. https://doi.org/10.1039/C4RA00821A
    80. Langxi Hu, Weijun Gui, Zichen Liu, Baishan Jiang. Synthesis of 3-aryl-2-aminoquinolines: palladium-catalyzed cascade reactions of gem-dibromovinylanilines with tert-butyl isocyanide and arylboronic acids. RSC Adv. 2014, 4 (72) , 38258-38262. https://doi.org/10.1039/C4RA05670A
    81. Gadi Ranjith Kumar, Yalla Kiran Kumar, Ruchir Kant, Maddi Sridhar Reddy. Tandem Cu-catalyzed ketenimine formation and intramolecular nucleophile capture: Synthesis of 1,2-dihydro-2-iminoquinolines from 1-( o -acetamidophenyl)propargyl alcohols. Beilstein Journal of Organic Chemistry 2014, 10 , 1255-1260. https://doi.org/10.3762/bjoc.10.125
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