Rhodium-Catalyzed Oxidative Coupling of Aryl Hydrazones with Internal Alkynes: Efficient Synthesis of Multisubstituted Isoquinolines

Abstract

An efficient rhodium-catalyzed oxidative coupling reaction has been developed that gives high yields of multisubstituted isoquinolines from easily accessible aryl hydrazones and internal alkynes. Indenone hydrazone can also be synthesized in high yield from the corresponding benzaldehyde hydrazone by using this approach.

Key words

alkynes - cyclization - hydrazones - heterocycles - rhodium - catalysis

• References


For selected books, see:
• 1a Eicher T, Hauptmann S. The Chemistry of Heterocycles: Structures, Reactions, Synthesis, and Applications. 2nd ed. Wiley-VCH; Weinheim: 2003
• 1b Joule JA, Mills K. Heterocyclic Chemistry . 4th ed. Blackwell Science; Oxford: 2000
• 1c Alajarín R, Burgos C In Modern Heterocyclic Chemistry . Vol. 1. Alvarez-Builla J, Vaquero JJ, Barluenga J. Wiley-VCH; Weinheim: 2011. Chap. 17; 1527

For selected examples, see:
• 2a Beasley SC, Cooper N, Gowers L, Gregory JP, Haughan AF, Hellewell PG, Macari D, Miotla J, Montana JG, Morgan T, Naylor R, Runcie KA, Tuladhar B, Warneck JB. H. Bioorg. Med. Chem. Lett. 1998; 8: 2629
• 2b van Muijlwijk-Koezen JE, Timmerman H, van der Goot H, Menge WM. P. B, Frijtag von Drabbe Künzel J, de Groote M, IJzerman AP. J. Med. Chem. 2000; 43: 2227
• 2c Reux B, Nevalainen T, Raitio KH, Koskinen AM. P. Bioorg. Med. Chem. 2009; 17: 4441
• 2d Chen Y, Sajjad M, Wang Y, Batt C, Nabi HA, Pandey RK. ACS Med. Chem. Lett. 2010; 2: 136
• 3a Herz W, Tocker S. J. Am. Chem. Soc. 1955; 77: 6355
• 3b Brown EV. J. Org. Chem. 1977; 42: 3208
• 3c Ishikawa T, Shimooka K, Narioka T, Noguchi S, Saito T, Ishikawa A, Yamazaki E, Harayama T, Seki H, Yamaguchi K. J. Org. Chem. 2000; 65: 9143
• 3d Youn SW. J. Org. Chem. 2006; 71: 2521
• 3e Xu X, Guo S, Dang Q, Chen J, Bai X. J. Comb. Chem. 2007; 9: 773
• 4a Dai G, Larock RC. Org. Lett. 2001; 4: 193
• 4b Roesch KR, Larock RC. J. Org. Chem. 2001; 67: 86
• 4c Huang Q, Hunter JA, Larock RC. J. Org. Chem. 2002; 67: 3437
• 4d Huang Q, Larock RC. J. Org. Chem. 2002; 68: 980
• 4e Huang Q, Larock RC. Tetrahedron Lett. 2002; 43: 3557
• 4f Dai G, Larock RC. J. Org. Chem. 2003; 68: 920
• 4g Konno T, Chae J, Miyabe T, Ishihara T. J. Org. Chem. 2005; 70: 10172
• 4h Korivi RP, Cheng C.-H. Org. Lett. 2005; 7: 5179
• 4i Gao H, Zhang J. Adv. Synth. Catal. 2009; 351: 85
• 4j Hwang S, Lee Y, Lee PH, Shin S. Tetrahedron Lett. 2009; 50: 2305

For recent reviews, see:
• 5a Larock RC, Zhang XX. Handbook of C–H Transformations . Vol. 1. Dyker G. Wiley-VCH; Weinheim: 2005: 309
• 5b Dick AR, Sanford MS. Tetrahedron 2006; 62: 2439
• 5c Daugulis O, Zaitsev VG, Shabashov D, Pham Q.-N, Lazareva A. Synlett 2006; 3382
• 5d Yu J.-Q, Giri R, Chen X. Org. Biomol. Chem. 2006; 4: 4041
• 5e Godula K, Sames D. Science 2006; 312: 67
• 5f Alberico D, Scott ME, Lautens M. Chem. Rev. 2007; 107: 174
• 5g Bergman RG. Nature 2007; 446: 391
• 5h Campos KR. Chem. Soc. Rev. 2007; 36: 1069
• 5i Deprez NR, Sanford MS. Inorg. Chem. 2007; 46: 1924
• 5j Lewis JC, Bergman RG, Ellman JA. Acc. Chem. Res. 2008; 41: 1013
• 5k Park YJ, Park J.-W, Jun C.-H. Acc. Chem. Res. 2008; 41: 222
• 5l Li B.-J, Yang S.-D, Shi Z.-J. Synlett 2008; 949
• 5m Chen X, Engle KM, Wang D.-H, Yu J.-Q. Angew. Chem. Int. Ed. 2009; 48: 5094
• 5n Lyons TW, Sanford MS. Chem. Rev. 2010; 110: 1147
• 5o Colby DA, Bergman RG, Ellman JA. Chem. Rev. 2010; 110: 624
• 5p Sun C.-L, Li B.-J, Shi Z.-J. Chem. Commun. 2010; 46: 677
• 5q Mkhalid IA. I, Barnard JH, Marder TB, Murphy JM, Hartwig JF. Chem. Rev. 2010; 110: 890
• 5r Ackermann L. Chem. Commun. 2010; 46: 4866
• 5s Jazzar R, Hitce J, Renaudat A, Sofack-Kreutzer J, Baudoin O. Chem. Eur. J. 2010; 16: 2654
• 5t Satoh T, Miura M. Chem. Eur. J. 2010; 16: 11212
• 5u Yeung CS, Dong VM. Chem. Rev. 2011; 111: 1215
• 5v McMurray L, Hara FO, Gaunt MJ. Chem. Soc. Rev. 2011; 40: 1885
• 5w Gutekunst WR, Baran PS. Chem. Soc. Rev. 2011; 40: 1976
• 5x Hartwig JF. Chem. Soc. Rev. 2011; 40: 1992
• 5y Wencel-Delord J, Droge T, Liu F, Glorius F. Chem. Soc. Rev. 2011; 40: 4740
• 5z Cho SH, Kim JY, Kwak J, Chang S. Chem. Soc. Rev. 2011; 40: 5068

For selected reviews, see:
• 6a Thansandote P, Lautens M. Chem. Eur. J. 2009; 15: 5874
• 6b Satoh T, Miura M. Synthesis 2010; 3395
• 6c Colby DA, Tsai AS, Bergman RG, Ellman JA. Acc. Chem. Res. 2011; 45: 814
• 6d Guimond N, Gorelsky SI, Fagnou K. J. Am. Chem. Soc. 2011; 133: 6449
• 6e Song G, Wang F, Li X. Chem. Soc. Rev. 2012; 41: 3651
• 6f Zhu C, Wang R, Falck JR. Chem. Asian J. 2012; 7: 1502
• 7a Lim S.-G, Lee JH, Moon CW, Hong J.-B, Jun C.-H. Org. Lett. 2003; 5: 2759
• 7b Colby DA, Bergman RG, Ellman JA. J. Am. Chem. Soc. 2008; 130: 3645
• 7c Parthasarathy K, Cheng C.-H. J. Org. Chem. 2009; 74: 9359
• 7d Guimond N, Fagnou K. J. Am. Chem. Soc. 2009; 131: 12050
• 7e Fukutani T, Umeda N, Hirano K, Satoh T, Miura M. Chem. Commun. 2009; 5141
• 7f Too PC, Wang Y.-F, Chiba S. Org. Lett. 2010; 12: 5688
• 7g Too PC, Chua SH, Wong SH, Chiba S. J. Org. Chem. 2011; 76: 6159
• 7h Wang Y.-F, Toh KK, Lee J.-Y, Chiba S. Angew. Chem. Int. Ed. 2011; 50: 5927
• 7i Wei X, Zhao M, Du Z, Li X. Org. Lett. 2011; 13: 4636
• 7j Zhang X, Chen D, Zhao M, Zhao J, Jia A, Li X. Adv. Synth. Catal. 2011; 353: 719
• 7k Yoshida Y, Kurahashi T, Matsubara S. Chem. Lett. 2011; 40: 1140
• 7l Jayakumar J, Parthasarathy K, Cheng C.-H. Angew. Chem. Int. Ed. 2012; 51: 197
• 8a Chinnagolla RK, Pimparkar S, Jeganmohan M. Org. Lett. 2012; 14: 3032
• 8b Kornhaaß C, Li J, Ackermann L. J. Org. Chem. 2012; 77: 9190
• 9 Li G, Ding Z, Xu B. Org. Lett. 2012; 14: 5338
• 10a Sun CY, Xu B. J. Org. Chem. 2008; 73: 7361
• 10b Ye WC, Mo J, Zhao TK, Xu B. Chem. Commun. 2009; 3246
• 10c Zhao TK, Xu B. Org. Lett. 2010; 12: 212
• 10d Wang CM, Sun CY, Weng F, Gao MC, Liu BX, Xu B. Tetrahedron Lett. 2011; 52: 2984
• 10e Shao J, Huang XM, Hong XH, Liu BX, Xu B. Synthesis 2012; 44: 1798
• 10f Liu BX, Hong XH, Yan D, Xu SG, Huang XM, Xu B. Org. Lett. 2012; 14: 4398
• 10g Xu SG, Huang XM, Hong XH, Xu B. Org. Lett. 2012; 14: 4614
• 10h Sun J, Liu BX, Xu B. RSC Adv. 2013; 3: 5824
• 11 Gareev M, Pudovik A. J. Gen. Chem. USSR (Engl. Transl.) 1976; 46: 1678
• 12 Gupta AK, Dubey DK, Parashar BD, Kaushik MP. Phosphorus, Sulfur Silicon Relat. Elem. 2008; 183: 1892
• 13 Sauro VA, Workentin MS. J. Org. Chem. 2001; 66: 831
• 14 Crystallographic data for compounds 3ha and 3la have been deposited with the accession numbers CCDC 917602 and 917601, respectively, and can be obtained free of charge from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; Fax: [phone]; E-mail: [e-mail]; Web site: www.ccdc.cam.ac.uk/conts/retrieving.html.