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
ACS Publications. Most Trusted. Most Cited. Most Read
My Activity
CONTENT TYPES

Rapid Access to 3-(Aminomethyl)isoquinoline-Fused Polycyclic Compounds by Copper-Catalyzed Four-Component Coupling, Cascade Cyclization, and Oxidation

View Author Information
Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo-ku, Kyoto 606-8501, Japan
Cite this: J. Org. Chem. 2009, 74, 16, 6299–6302
Publication Date (Web):July 2, 2009
https://doi.org/10.1021/jo901090u
Copyright © 2009 American Chemical Society

    Article Views

    2734

    Altmetric

    -

    Citations

    LEARN ABOUT THESE METRICS
    Other access options
    Supporting Info (2)»

    Abstract

    Abstract Image

    A novel copper-catalyzed synthesis of 3-(aminomethyl)isoquinoline-fused polycyclic compounds, through four-component coupling, cyclization, and oxidation, has been developed. A Mannich-type reaction of 2-ethynylbenzaldehyde with paraformaldehyde and a secondary amine followed by treatment with a diamine component gave tricyclic isoquinolines through cascade cyclization and oxidation. Construction of fused isoquinolines of various ring sizes is also presented.

    Read this article

    To access this article, please review the available access options below.

    Get instant access

    Purchase Access

    Read this article for 48 hours. Check out below using your ACS ID or as a guest.

    Recommended

    Access through Your Institution

    You may have access to this article through your institution.

    Your institution does not have access to this content. You can change your affiliated institution below.

    Supporting Information

    ARTICLE SECTIONS
    Jump To

    Experimental procedures, full characterization, and 1H and 13C NMR charts of the 2-ethynylbenzaldehydes and cyclization products and a crystallographic information file for 12a. This material is available free of charge 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 63 publications.

    1. Shi-Yi Yuan, Qi-Qi Yan, Dan Wang, Ting-Ting Dan, Long He, Cheng-Yu He, Wen-Dao Chu, Quan-Zhong Liu. Asymmetric Synthesis of 3-Methyleneindolines via Rhodium(I)-Catalyzed Alkynylative Cyclization of N-(o-Alkynylaryl)imines. Organic Letters 2021, 23 (12) , 4823-4827. https://doi.org/10.1021/acs.orglett.1c01518
    2. Mariam A. Mehdi, Eric A. C. Bushnell, Sahar Nikoo, James W. Gauld, James R. Green. Generation and Reactions of a Benzodehydrotropylium Ion–Co2(CO)6 Complex. ACS Omega 2019, 4 (20) , 18600-18608. https://doi.org/10.1021/acsomega.9b02390
    3. Liangbin Huang, Matthias Arndt, Käthe Gooßen, Heinrich Heydt, and Lukas J. Gooßen . Late Transition Metal-Catalyzed Hydroamination and Hydroamidation. Chemical Reviews 2015, 115 (7) , 2596-2697. https://doi.org/10.1021/cr300389u
    4. Huangdi Feng, Huihui Jia, and Zhihua Sun . Mild and Catalyst-Free Petasis/Decarboxylative Domino Reaction: Chemoselective Synthesis of N-Benzyl Propargylamines. The Journal of Organic Chemistry 2014, 79 (23) , 11812-11818. https://doi.org/10.1021/jo502349a
    5. Akhilesh K. Verma, Deepak Choudhary, Rakesh K. Saunthwal, Vineeta Rustagi, Monika Patel, and Rakesh K. Tiwari . On Water: Silver-Catalyzed Domino Approach for the Synthesis of Benzoxazine/Oxazine-Fused Isoquinolines and Naphthyridines from o-Alkynyl Aldehydes. The Journal of Organic Chemistry 2013, 78 (13) , 6657-6669. https://doi.org/10.1021/jo4009639
    6. Akhilesh K. Verma, Siva K. Reddy Kotla, Deepak Choudhary, Monika Patel, and Rakesh K. Tiwari . Silver-Catalyzed Tandem Synthesis of Naphthyridines and Thienopyridines via Three-Component Reaction. The Journal of Organic Chemistry 2013, 78 (9) , 4386-4401. https://doi.org/10.1021/jo400400c
    7. Jinsong Peng, Guoning Shang, Chunxia Chen, Zhongshuo Miao, and Bin Li . Nucleophilic Addition of Benzimidazoles to Alkynyl Bromides/Palladium-Catalyzed Intramolecular C–H Vinylation: Synthesis of Benzo[4,5]imidazo[2,1-a]isoquinolines. The Journal of Organic Chemistry 2013, 78 (3) , 1242-1248. https://doi.org/10.1021/jo302471z
    8. Zhi-Xiong Ma, John B. Feltenberger, and Richard P. Hsung . Total Syntheses of Chelidonine and Norchelidonine via an Enamide–Benzyne–[2 + 2] Cycloaddition Cascade. Organic Letters 2012, 14 (11) , 2742-2745. https://doi.org/10.1021/ol300967a
    9. Yamato Suzuki, Saori Naoe, Shinya Oishi, Nobutaka Fujii, and Hiroaki Ohno . Gold-Catalyzed Three-Component Annulation: Efficient Synthesis of Highly Functionalized Dihydropyrazoles from Alkynes, Hydrazines, and Aldehydes or Ketones. Organic Letters 2012, 14 (1) , 326-329. https://doi.org/10.1021/ol203072u
    10. Huang-Che Ouyang, Ri-Yuan Tang, Ping Zhong, Xing-Guo Zhang, and Jin-Heng Li . CuI/I2-Promoted Electrophilic Tandem Cyclization of 2-Ethynylbenzaldehydes with ortho-Benzenediamines: Synthesis of Iodoisoquinoline-Fused Benzimidazoles. The Journal of Organic Chemistry 2011, 76 (1) , 223-228. https://doi.org/10.1021/jo102060j
    11. Roland E. Dolle, Bertrand Le Bourdonnec, Karin Worm, Guillermo A. Morales, Craig J. Thomas, and Wei Zhang . Comprehensive Survey of Chemical Libraries for Drug Discovery and Chemical Biology: 2009. Journal of Combinatorial Chemistry 2010, 12 (6) , 765-806. https://doi.org/10.1021/cc100128w
    12. Xingxin Yu, Zhiyuan Chen, Xiaodi Yang and Jie Wu . Tandem Reactions of N′-(2-Alkynylbenzylidene)hydrazides with Silyl Enolates: A Facile Route to H-Pyrazolo[5,1-a]isoquinolines. Journal of Combinatorial Chemistry 2010, 12 (3) , 374-378. https://doi.org/10.1021/cc1000314
    13. Zefeng Jin, Guodong Shen, Xin Lv. Recent Advances in Domino Synthesis of Fused Polycyclic N ‐Heterocycles Based on Intramolecular Alkyne Hydroamination under Copper Catalysis. Chinese Journal of Chemistry 2023, 41 (24) , 3751-3771. https://doi.org/10.1002/cjoc.202300449
    14. Wanfang Li, Xiao‐Feng Wu. Formaldehyde as C 1 Synthon in Organic Synthesis. 2022, 157-247. https://doi.org/10.1002/9783527831883.ch5
    15. Marko Hapke. Pyridines and Benzo Derivatives: Synthesis. 2022, 150-216. https://doi.org/10.1016/B978-0-12-818655-8.00108-6
    16. 伍超 翟. Bronsted Acid-Catalyzed One-Pot Synthesis of 3-Aminoindan-1-Ones through a Domino Reaction. Journal of Organic Chemistry Research 2022, 10 (02) , 39-49. https://doi.org/10.12677/JOCR.2022.102004
    17. Muthu Karuppasamy, B.S. Vachan, Vellaisamy Sridharan. Copper catalysis for the synthesis of quinolines and isoquinolines. 2021, 249-288. https://doi.org/10.1016/B978-0-12-821263-9.00007-2
    18. Jie-Ren Deng, Nathanael Chun-Him Lai, Karen Ka-Yan Kung, Bin Yang, Sai-Fung Chung, Alan Siu-Lun Leung, Man-Chung Choi, Yun-Chung Leung, Man-Kin Wong. N-Terminal selective modification of peptides and proteins using 2-ethynylbenzaldehydes. Communications Chemistry 2020, 3 (1) https://doi.org/10.1038/s42004-020-0309-y
    19. Jingxin Tian, Shanshan Yuan, Fuhong Xiao, Huawen Huang, Guo-Jun Deng. Concise synthesis of N -thiomethyl benzoimidazoles through base-promoted sequential multicomponent assembly. RSC Advances 2019, 9 (52) , 30570-30574. https://doi.org/10.1039/C9RA06144D
    20. Manisha Mishra, Dylan Twardy, Clifford Ellstrom, Kraig A. Wheeler, Roman Dembinski, Béla Török. Catalyst-free ambient temperature synthesis of isoquinoline-fused benzimidazoles from 2-alkynylbenzaldehydes via alkyne hydroamination. Green Chemistry 2019, 21 (1) , 99-108. https://doi.org/10.1039/C8GC02520G
    21. Zheng Xu, Hui Wu, Huaigui Li, Zhengyin Du, Ying Fu. Copper‐Catalyzed Highly Efficient Acetylene‐Mannich Reaction of Secondary Amines, Paraformaldehyde and Terminal Alkynes. ChemistrySelect 2018, 3 (48) , 13629-13631. https://doi.org/10.1002/slct.201803313
    22. Azusa Kondoh, Masahiro Terada. Brønsted Base‐Catalyzed Umpolung Intramolecular Cyclization of Alkynyl Imines. Chemistry – A European Journal 2018, 24 (16) , 3998-4001. https://doi.org/10.1002/chem.201800219
    23. Valentin D. Gvozdev, Konstantin N. Shavrin, Mikhail P. Egorov, Oleg M. Nefedov. New selective cyclizations of alk-4-ynals with primary amines and azoles:one-pot synthesis of 2-azolylpyrrolidines and 3-iminocyclopentenes. Mendeleev Communications 2018, 28 (2) , 123-125. https://doi.org/10.1016/j.mencom.2018.03.002
    24. Run Sun, Yu Jiang, Xiang‐Ying Tang, Min Shi. Rhodium(II)‐Catalyzed and Thermally Induced Intramolecular Migration of N ‐Sulfonyl‐1,2,3‐triazoles: New Approaches to 1,2‐Dihydroisoquinolines and 1‐Indanones. Chemistry – A European Journal 2016, 22 (16) , 5727-5733. https://doi.org/10.1002/chem.201504914
    25. Jun He, Yinping Shi, Wanli Cheng, Zengming Man, Dongdong Yang, Chuan‐Ying Li. Rhodium‐Catalyzed Synthesis of 4‐Bromo‐1,2‐dihydroisoquinolines: Access to Bromonium Ylides by the Intramolecular Reaction of a Benzyl Bromide and an α‐Imino Carbene. Angewandte Chemie 2016, 128 (14) , 4633-4637. https://doi.org/10.1002/ange.201512015
    26. Jun He, Yinping Shi, Wanli Cheng, Zengming Man, Dongdong Yang, Chuan‐Ying Li. Rhodium‐Catalyzed Synthesis of 4‐Bromo‐1,2‐dihydroisoquinolines: Access to Bromonium Ylides by the Intramolecular Reaction of a Benzyl Bromide and an α‐Imino Carbene. Angewandte Chemie International Edition 2016, 55 (14) , 4557-4561. https://doi.org/10.1002/anie.201512015
    27. Xiufang Cheng, Huamin Wang, Fuhong Xiao, Guo-Jun Deng. Lewis acid-catalyzed 2-arylquinazoline formation from N′-arylbenzimidamides and paraformaldehyde. Green Chemistry 2016, 18 (21) , 5773-5776. https://doi.org/10.1039/C6GC02319C
    28. Pawan K. Mishra, Akhilesh K. Verma. Metal-free regioselective tandem synthesis of diversely substituted benzimidazo-fused polyheterocycles in aqueous medium. Green Chemistry 2016, 18 (23) , 6367-6372. https://doi.org/10.1039/C6GC02330D
    29. Wanfang Li, Xiao‐Feng Wu. The Applications of (Para)formaldehyde in Metal‐Catalyzed Organic Synthesis. Advanced Synthesis & Catalysis 2015, 357 (16-17) , 3393-3418. https://doi.org/10.1002/adsc.201500753
    30. Valentin D. Gvozdev, Konstantin N. Shavrin, Mikhail P. Egorov, Oleg M. Nefedov. One-pot synthesis of 1-arylmethylidene-1,2,3,3a-tetrahydro-5H-pyrrolo[1,2-a]-[3,1]benzoxazines and 1-arylmethylidene-1,2,3,3a,4,5-hexahydropyrrolo[1,2-a]-quinazolines from 5-arylalk-4-ynals and o-aminobenzylic alcohol/amine. Mendeleev Communications 2015, 25 (5) , 329-331. https://doi.org/10.1016/j.mencom.2015.09.002
    31. Nandigama Satish Kumar, L. Chandrasekhara Rao, N. Jagadeesh Babu, H. M. Meshram. A domino green method for the rapid synthesis of novel fused isoquinoline derivatives via Knoevenagel/Michael/cyclization reactions on aqueous media and their photophysical properties. RSC Advances 2015, 5 (116) , 95539-95544. https://doi.org/10.1039/C5RA15948B
    32. Zhuo Xin, Søren Kramer, Jacob Overgaard, Troels Skrydstrup. Access to 1,2‐Dihydroisoquinolines through Gold‐Catalyzed Formal [4+2] Cycloaddition. Chemistry – A European Journal 2014, 20 (26) , 7926-7930. https://doi.org/10.1002/chem.201403290
    33. Rajeev Ranjan Jha, Trapti Aggarwal, Akhilesh Kumar Verma. Stereoselective tandem synthesis of oxazolo-fused pyrroloquinolines from o-alkynylaldehydes via Ag(I)-catalyzed regioselective 5-exo-dig ring closure. Tetrahedron Letters 2014, 55 (16) , 2603-2608. https://doi.org/10.1016/j.tetlet.2014.02.103
    34. Rajeev Ranjan Jha, Abhinandan Kumar Danodia, Sushil Kumar, Akhilesh Kumar Verma. Au(III)-catalyzed regio- and stereoselective tandem synthesis of oxazolo fused naphthyridines and isoquinolines from o-alkynylaldehydes. Tetrahedron Letters 2014, 55 (3) , 610-615. https://doi.org/10.1016/j.tetlet.2013.11.072
    35. Rajeev R. Jha, Rakesh K. Saunthwal, Akhilesh K. Verma. Stereoselective tandem synthesis of thiazolo fused naphthyridines and thienopyridines from o-alkynylaldehydes via Au( iii )-catalyzed regioselective 6-endo-dig ring closure. Org. Biomol. Chem. 2014, 12 (4) , 552-556. https://doi.org/10.1039/C3OB42035C
    36. Sudipta Kumar Manna, Gautam Panda. Microwave assisted [RuCl 2 (p-cymene) 2 ] 2 catalyzed regioselective endo-tandem cyclization involving imine and alkyne activation: an approach to benzo[4,5]imidazo[2,1-a]pyridine scaffold. RSC Adv. 2014, 4 (40) , 21032-21041. https://doi.org/10.1039/C4RA02581D
    37. Giorgio Abbiati, Elisabetta Rossi. Silver and gold-catalyzed multicomponent reactions. Beilstein Journal of Organic Chemistry 2014, 10 , 481-513. https://doi.org/10.3762/bjoc.10.46
    38. Pradip Kumar Maji, Rafique Ul Islam, Sujit Kumar Bera. RECENT PROGRESS IN METAL ASSISTED MULTICOMPONENT SYNTHESES OF HETEROCYCLES. HETEROCYCLES 2014, 89 (4) , 869. https://doi.org/10.3987/REV-13-781
    39. Susanta Kumar Manna, Suresh Kumar Mondal, Atiur Ahmed, Arabinda Mandal, Atanu Jana, Mohammed Ikbal, Shubhankar Samanta, Jayanta K. Ray. One-pot synthesis of highly fluorescent polycyclic benzimidazole derivatives. RSC Advances 2013, 4 (5) , 2474-2481. https://doi.org/10.1039/C3RA44521F
    40. V. D. Gvozdev, K. N. Shavrin, O. M. Nefedov. Synthesis of bicyclic N,N-enaminals by cyclization of alk-4-ynals with aliphatic diamines in DMSO upon treatment with KOH. Russian Chemical Bulletin 2013, 62 (11) , 2430-2437. https://doi.org/10.1007/s11172-013-0351-3
    41. Hiroaki Chiba, Yuki Sakai, Ayako Ohara, Shinya Oishi, Nobutaka Fujii, Hiroaki Ohno. Convergent Synthesis of (−)‐Quinocarcin Based on the Combination of Sonogashira Coupling and Gold(I)‐Catalyzed 6‐ endo ‐ dig Hydroamination. Chemistry – A European Journal 2013, 19 (27) , 8875-8883. https://doi.org/10.1002/chem.201300687
    42. Sisi Li, Ziyong Li, Shuyuan Huang, Jun Yin, Sheng Hua Liu. Synthesis, Photochromism, and Effects of Metal Ions on Fluorescence of Dithienylethenes Containing Imidazo[2,1-a]isoquinoline. Synthetic Communications 2013, 43 (11) , 1530-1537. https://doi.org/10.1080/00397911.2011.644845
    43. Konstantin N. Shavrin, Valentin D. Gvozdev, Oleg M. Nefedov. Synthesis of 6-(arylmethylidene)octahydropyrrolo[1,2-a]pyrimidines and 5-(arylmethylidene)hexahydropyrrolo[1,2-a]imidazoles by the interaction of alk-4-ynals with a,?-diaminoalkanes in DMSO in the presence of KOH. Mendeleev Communications 2013, 23 (3) , 140-141. https://doi.org/10.1016/j.mencom.2013.05.006
    44. Mingming Li, Ping Xing, Zuogang Huang, Biao Jiang. One‐pot Synthesis of Aromatic Fused 2,3‐Dihydroindanone by Tandem Pauson‐Khand/Michael/Henry Reaction. Chinese Journal of Chemistry 2013, 31 (1) , 49-54. https://doi.org/10.1002/cjoc.201201118
    45. Kazuhiro Kobayashi, Kosuke Ezaki, Toshihide Komatsu. Convenient Synthesis of 6-Amino-3,4-dihydro-2H-pyrimido[2,1-a]isoquinoline-7-carbonitriles and 5-Amino-2,3-dihydroimidazo[2,1-a]isoquinoline-6-carbonitriles. HETEROCYCLES 2013, 87 (9) , 1925. https://doi.org/10.3987/COM-13-12777
    46. Hiroaki Chiba, Shinya Oishi, Nobutaka Fujii, Hiroaki Ohno. Total Synthesis of (−)‐Quinocarcin by Gold(I)‐Catalyzed Regioselective Hydroamination. Angewandte Chemie 2012, 124 (36) , 9303-9306. https://doi.org/10.1002/ange.201205106
    47. Hiroaki Chiba, Shinya Oishi, Nobutaka Fujii, Hiroaki Ohno. Total Synthesis of (−)‐Quinocarcin by Gold(I)‐Catalyzed Regioselective Hydroamination. Angewandte Chemie International Edition 2012, 51 (36) , 9169-9172. https://doi.org/10.1002/anie.201205106
    48. Vineeta Rustagi, Rakesh Tiwari, Akhilesh Kumar Verma. Ag I ‐Catalyzed Cascade Strategy: Regioselective Access to Diversely Substituted Fused Benzimidazo[2,1‐ a ]isoquinolines, Naphthyridines, Thienopyridines, and Quinoxalines in Water. European Journal of Organic Chemistry 2012, 2012 (24) , 4590-4602. https://doi.org/10.1002/ejoc.201200546
    49. Meng-Yang Chang, Ming-Hao Wu, Yeh-Long Chen. Synthesis of dihydrobenzoimidazo[2,1-a]isoquinolines. Tetrahedron Letters 2012, 53 (32) , 4156-4160. https://doi.org/10.1016/j.tetlet.2012.05.132
    50. Long Lin, Qiongyou Wu, Shaowei Huang, Guangfu Yang. Facile Synthesis of 3‐Substituted Isoquinolines Derivatives via Microwave‐assisted Tandem Three‐component Coupling Cyclization. Chinese Journal of Chemistry 2012, 30 (5) , 1075-1082. https://doi.org/10.1002/cjoc.201100560
    51. Jiangtao Zhu, Haibo Xie, Zixian Chen, Shan Li, Yongming Wu. A detailed study of the intramolecular hydroamination of N-(ortho-alkynyl)aryl-N′-substituted trifluoroacetamidines and bromodifluoroacetamidines. Org. Biomol. Chem. 2012, 10 (3) , 516-523. https://doi.org/10.1039/C1OB06528A
    52. T. Krishna Chaitanya, K.S. Prakash, Rajagopal Nagarajan. Metal-free synthesis of benzimidazo[2,1-a]ellipticines via tandem inter and intramolecular cyclization. Tetrahedron 2011, 67 (36) , 6934-6938. https://doi.org/10.1016/j.tet.2011.06.076
    53. Yusuke Tokimizu, Yusuke Ohta, Hiroaki Chiba, Shinya Oishi, Nobutaka Fujii, Hiroaki Ohno. Direct synthesis of highly fused perimidines by copper(I)-catalyzed hydroamination of 2-ethynylbenzaldehydes. Tetrahedron 2011, 67 (29) , 5168-5175. https://doi.org/10.1016/j.tet.2011.05.051
    54. Xingxin Yu, Xiaolin Pan, Jie Wu. An efficient route to diverse H-pyrazolo[5,1-a]isoquinolines via sequential multi-component/cross-coupling reactions. Tetrahedron 2011, 67 (6) , 1145-1149. https://doi.org/10.1016/j.tet.2010.12.005
    55. Kamaraj Balamurugan, Veerappan Jeyachandran, Subbu Perumal, J. Carlos Menéndez. A three-component domino protocol for the facile synthesis of highly functionalized tetrahydroisoquinolines by creation of their benzene ring. Tetrahedron 2011, 67 (7) , 1432-1437. https://doi.org/10.1016/j.tet.2010.12.052
    56. Philip E. Alford. Six-Membered Ring Systems: Pyridines and Benzo Derivatives. 2011, 349-391. https://doi.org/10.1016/S0959-6380(11)22012-9
    57. Vineeta Rustagi, Trapti Aggarwal, Akhilesh K. Verma. Highly efficient Ag(i)-catalyzed regioselective tandem synthesis of diversely substituted quinoxalines and benzimidazoles in water. Green Chemistry 2011, 13 (7) , 1640. https://doi.org/10.1039/c1gc15346c
    58. Bo Jiang, Trideep Rajale, Walter Wever, Shu‐Jiang Tu, Guigen Li. Multicomponent Reactions for the Synthesis of Heterocycles. Chemistry – An Asian Journal 2010, 5 (11) , 2318-2335. https://doi.org/10.1002/asia.201000310
    59. Weijun Fu, Mei Zhu, Guanglong Zou. An efficient synthesis of ring‐fused indoles via copper‐catalyzed tandem reaction of N ‐( o ‐alkynylphenyl)imines. Applied Organometallic Chemistry 2010, 24 (7) , 499-502. https://doi.org/10.1002/aoc.1648
    60. Yusuke OHTA. Construction of Indole- and Isoquinoline-fused Nitrogen-containing Heterocycles through Copper-catalyzed Multi-component Reaction. YAKUGAKU ZASSHI 2010, 130 (7) , 925-936. https://doi.org/10.1248/yakushi.130.925
    61. Nitin T. Patil, Anil Kumar Mutyala, Pediredla G. V. V. Lakshmi, Penmatcha V. K. Raju, Balasubramanian Sridhar. Facile Assembly of Fused Isoquinolines by Gold(I)‐Catalyzed Coupling–Cyclization Reactions between o ‐Alkynylbenzaldehydes and Aromatic Amines Containing Tethered Nucleophiles. European Journal of Organic Chemistry 2010, 2010 (10) , 1999-2007. https://doi.org/10.1002/ejoc.200901364
    62. Yusuke Ohta, Yushi Kubota, Tsuyoshi Watabe, Hiroaki Chiba, Shinya Oishi, Nobutaka Fujii, Hiroaki Ohno. ChemInform Abstract: Rapid Access to 3‐(Aminomethyl)isoquinoline‐Fused Polycyclic Compounds by Copper‐Catalyzed Four‐Component Coupling, Cascade Cyclization, and Oxidation.. ChemInform 2010, 41 (2) https://doi.org/10.1002/chin.201002181
    63. Shengqing Ye, Xiaodi Yang, Jie Wu. Silver triflate-catalyzed three-component reaction of 2-alkynylbenzaldehyde, sulfonohydrazide, and α,β-unsaturated carbonyl compound. Chemical Communications 2010, 46 (29) , 5238. https://doi.org/10.1039/c0cc00905a