Silver Nitrate Mediated Cyclization/N–N Bond-Cleavage Reaction for the Synthesis of 3-Arylisoquinolines

Abstract

An unprecedented silver nitrate mediated novel transformation of aromatic hydrazones into various isoquinolines has been developed. This method involves a silver nitrate promoted cyclization of aromatic hydrazones followed by N–N bond cleavage, and has wide substrate scope under mild conditions.

Key words

isoquinolines - bond cleavage - hydrazones - silver nitrate - alkynals - domino reactions

• References and Notes

• 1a Chrzanowska M, Rozwadowska MD. Chem. Rev. 2004; 104: 3341
• 1b Giri P, Kumar GS. Mini-Rev. Med. Chem. 2010; 10: 568
• 2a Negishi E.-i, Copéret C, Ma S, Liou S.-Y, Liu F. Chem. Rev. 1996; 96: 365
• 2b Aoki S, Watanabe Y, Sanagawa M, Setiawan A, Kotoku N, Kobayashi M. J. Am. Chem. Soc. 2006; 128: 3148
• 2c Wada Y, Nishida N, Kurono N, Ohkuma T, Orito K. Eur. J. Org. Chem. 2007; 4320
• 2d Sun Y, Xun K, Wang Y, Chen X. Anti-Cancer Drugs 2009; 20: 757
• 2e Li Y.-H, Yang P, Kong W.-J, Wang Y.-X, Hu C.-Q, Zuo Z.-Y, Wang Y.-M, Gao H, Gao L.-M, Feng Y.-C, Du N.-N, Liu Y, Song D.-Q, Jiang J.-D. J. Med. Chem. 2009; 52: 492
• 2f Zhang S, Huang D, Xu G, Cao S, Wang R, Peng S, Sun J. Org. Biomol. Chem. 2015; 13: 7920
• 3a Nakamura I, Yamamoto Y. Chem. Rev. 2004; 104: 2127
• 3b Zeni G, Larock RC. Chem. Rev. 2004; 104: 2285
• 3c Uchiyama M, Furuyama T, Kobayashi M, Matsumoto Y, Tanaka K. J. Am. Chem. Soc. 2006; 128: 8404
• 3d Furuyama T, Yonehara M, Arimoto S, Kobayashi M, Matsumoto Y, Uchiyama M. Chem. Eur. J. 2008; 14: 10348
• 3e Seomoon D, Lee PH. J. Org. Chem. 2008; 73: 1165
• 3f Korivi RP, Cheng C.-H. Chem. Eur. J. 2010; 16: 282
• 3g Lee K, Kim H, Mo J, Lee PH. Chem. Asian J. 2011; 6: 2147
• 3h Liu Y, Zeng R, Pan J, Zou J. Chin. J. Chem. 2014; 32: 883
• 3i Shi L, Ji Y, Huang W, Zhou Y. Acta Chim. Sin. 2014; 72: 820 ; DOI: 10.6023/A14050391
• 4a Vachhani DD, Mehta VP, Modha SG, Van Hecke K, VanMeervelt L, Van der Eycken E. Adv. Synth. Catal. 2012; 354: 1593
• 4b Roesch KR, Larock RC. J. Org. Chem. 2002; 67: 86
• 5a Chen Z, Gao L, Ye S, Ding Q, Wu J. Chem. Commun. 2012; 48: 3975
• 5b Xiao Q, Sheng J, Ding Q, Wu J. Adv. Synth. Catal. 2013; 355: 2321
• 6a He R, Huang Z.-T, Zheng Q.-Y, Wang C. Angew. Chem. Int. Ed. 2014; 53: 4950
• 6b Zhou B, Chen H, Wang C. J. Am. Chem. Soc. 2013; 135: 1264
• 6c Dell’Acqua M, Abbiati G, Rossi E. Synlett 2010; 2672
• 7a Salvatore RN, Yoon CH, Jung KW. Tetrahedron 2001; 57: 7785
• 7b Kienle M, Dubbaka SR, Brade K, Knochel P. Eur. J. Org. Chem. 2007; 4166
• 8a Han W, Zhang G, Li G, Huang H. Org. Lett. 2014; 16: 3532
• 8b Huang X.-C, Yang X.-H, Song R.-J, Li J.-H. J. Org. Chem. 2014; 79: 1025
• 8c Chuang S.-C, Gandeepan P, Cheng C.-H. Org. Lett. 2013; 15: 5750
• 8d Subbarao KP. V, Reddy GR, Muralikrishna A, Reddy KV. J. Heterocycl. Chem. 2014; 51: 1045
• 9a Verma AK, Kotla SK. R, Choudhary D, Patel M, Tiwari RK. J. Org. Chem. 2013; 78: 4386
• 9b Verma AK, Choudhary D, Saunthwal RK, Rustagi V, Patel M, Tiwari RK. J. Org. Chem. 2013; 78: 6657
• 10a Zhao Y.-H, Li Y, Guo T, Tang Z, Deng K, Zhao G. Synth. Commun. 2016; 46: 355
• 10b Zhao Y.-H, Li Y, Guo T, Tang Z, Xie W, Zhao G. Tetrahedron Lett. 2016; 57: 2257
• 10c Li Y, Zhao Y, Luo M, Tang Z, Cao C, Deng K. Chin. J. Org. Chem. 2016; DOI: 10.6023/cjoc201604031.
• 11 Ghavtadze N, Fröhlich R, Würthwein E.-U. Eur. J. Org. Chem. 2010; 1787
• 12 3-Phenylisoquinolines (2a); ¹³ Typical ProcedureTo a solution of 2-(phenylethynyl)benzaldehyde (1a; 62.0 mg, 0.3 mmol) in EtOH (5 mL) was added N₂H₄·HCl (30.6 mg, 0.45 mmol), and the mixture was stirred at r.t. for 3 h. The solid was then collected by filtration and used in the next step without further purification. The crude aromatic hydrazones 3a was dissolved in DMSO (3 mL) and AgNO₃ (51.0 mg, 0.3 mmol) was added. The mixture was stirred at 100 °C until all starting material was consumed. The solvent was evaporated and the residue was purified by column chromatography, eluting with ­hexanes/EtOAc (5:1) to give a white solid; yield: 35 mg (57%); mp 97–99 °C; ¹H NMR (500 MHz, CDCl₃): δ = 9.37 (s, 1 H), 8.16 (d, J = 7.5 Hz, 2 H), 8.10 (s, 1 H), 8.02 (d, J = 8.0 Hz, 1 H), 7.91–7.89 (d, J = 8.0 Hz, 1 H), 7.75–7.70 (m, 1 H), 7.63–7.60 (m, 1 H), 7.56–7.53 (m, 2 H), 7.47–7.44 (m, 1 H); ¹³C NMR (125 MHz, CDCl₃): δ = 152.5 , 151.3, 139.6, 136.7, 130.6, 128.8, 128.6, 127.8, 127.6, 127.1, 127.0, 126.9, 116.6. The NMR data agreed with those previously reported.
• 13 Niu Y.-N, Yan Z.-Y, Gao G.-L, Wang H.-L, Shu X.-Z, Ji K.-G, Liang Y.-M. J. Org. Chem. 2009; 74: 2893