Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2019; 51(12): 2506-2514
DOI: 10.1055/s-0037-1611795
DOI: 10.1055/s-0037-1611795
special topic
Ruthenium-Catalyzed Annulation of N-Cbz Hydrazones via C–H/N–N Bond Activation for the Rapid Synthesis of Isoquinolines
The author D. S. D. would like to thank the University Grants Commission (UGC), New Delhi, India for providing a Senior Research Fellowship under Basic Science Research (BSR) scheme [F.25-1/2014-15, F.7-227/2009, 16th Feb 2015].Further Information
Publication History
Received: 26 February 2019
Accepted: 19 March 2019
Publication Date:
10 April 2019 (online)
Published as part of the Special Topic Ruthenium in Organic Synthesis
Abstract
In this work, N-Cbz hydrazone has been employed as a rarely explored directing group for the synthesis of isoquinolines by annulation with internal alkynes via C–H/N–N activation using Ru catalyst. Additive as well as external oxidant-free rapid protocol has been established for the synthesis of isoquinolines using microwave strategy. Use of non-volatile and biodegradable PEG as a green solvent with lower catalyst loading makes the proposed protocol environmentally benign. Further, higher functional group tolerance and wide substrate scope has been observed under the stated methodology with higher yields.
Key words
C–H/N–N activation - ruthenium - microwave-assisted - isoquinolines - annulation - hydrazonesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1611795.
- Supporting Information
-
References
- 1a Dyker G. Angew. Chem. Int. Ed. 1999; 38: 1698
- 1b Yamaguchi J, Yamaguchi AD, Itami K. Angew. Chem. Int. Ed. 2012; 51: 8960
- 1c Chen DY.-K, Youn SW. Chem. Eur. J. 2012; 18: 9452
- 1d Kuhl N, Hopkinson MN, Wencel-Delord J, Glorius F. Angew. Chem. Int. Ed. 2012; 51: 10236
- 1e Engle KM, Mei T.-S, Wasa M, Yu J.-Q. Acc. Chem. Res. 2012; 45: 788
- 1f McMurray L, O’Hara F, Gaunt MJ. Chem. Soc. Rev. 2011; 40: 1885
- 1g Cho SH, Kim JY, Kwak J, Chang S. Chem. Soc. Rev. 2011; 40: 5068
- 1h Wencel-Delord J, Dröge T, Liu F, Glorius F. Chem. Soc. Rev. 2011; 40: 4740
- 1i Lyons T, Sanford M. Chem. Rev. 2010; 110: 1147
- 1j Wencel-Delord J, Glorius F. Nat. Chem. 2013; 5: 369
- 1k White MC. Science 2012; 335: 807
- 2a Sarkar SD, Liu W, Kozhushkov SI, Ackermann L. Adv. Synth. Catal. 2014; 356: 1461
- 2b Manikandan R, Jeganmohan M. Org. Biomol. Chem. 2015; 13: 10420
- 2c Leitch JA, Frost CG. Chem. Soc. Rev. 2017; 46: 7145
- 2d Arockiam PB, Bruneau C, Dixneuf PH. Chem. Rev. 2012; 112: 5879
- 2e Zhang Z, Jiang H, Huang Y. Org. Lett. 2014; 16: 5976
- 2f Zha G.-F, Qin H.-L, Kantchev EA. B. RSC Adv. 2016; 6: 30875
- 2g Keim W, Dahmen G, Deckers G, Kranenburg P. Russ. Chem. Bull. 1994; 43: 543
- 2h Gollapelli KK, Kallepu S, Govindappa N, Nanubolu JB, Chegondi R. Chem. Sci. 2016; 7: 4748
- 2i Das R, Kapur M. Chem. Asian J. 2015; 10: 1505
- 2j Park Y, Jeon I, Shin S, Min J, Lee PH. J. Org. Chem. 2013; 78: 10209
- 3a Chen Z, Wang B, Zhang J, Yu W, Liu Z, Zhang Y. Org. Chem. Front. 2015; 2: 1107
- 3b Zhang M, Zhang Y, Jie X, Zhao H, Li G, Su W. Org. Chem. Front. 2014; 1: 843
- 3c Sun H, Guimond N, Huang Y. Org. Biomol. Chem. 2016; 14: 8389
- 3d Wang K, Hu F, Zhang Y, Wang J. Sci. China Chem. 2015; 58: 1252
- 4a Wang Z, Xie P, Xia Y. Chin. Chem. Lett. 2018; 29: 47
- 4b Huang X, Huang J, Du C, Zhang X, Song F, You J. Angew. Chem. Int. Ed. 2013; 52: 12970
- 4c Mo J, Wang L, Cui X. Org. Lett. 2015; 17: 4960
- 4d Kalsi D, Sundararaju B. Org. Lett. 2015; 17: 6118
- 4e Raju S, Annamalai P, Chen P.-L, Liu Y.-H, Chuang S.-C. Org. Lett. 2017; 19: 4134
- 4f Li XG, Liu K, Zou G, Liu PN. Adv. Synth. Catal. 2014; 356: 1496
- 4g Lu Q, Greßies S, Cembellin S, Klauck FJ. R, Daniliuc CG, Glorius F. Angew. Chem. Int. Ed. 2017; 56: 12778
- 4h Huang H, Ji X, Wua W, Jiang H. Chem. Soc. Rev. 2015; 44: 1155
- 4i Zhang S, Huang D, Xu G, Cao S, Wang R, Peng S, Sun J. Org. Biomol. Chem. 2015; 13: 7920
- 4j Huang H, Cai J, Deng G.-J. Org. Biomol. Chem. 2016; 14: 1519
- 4k Kaishap PP, Sarmab B, Gogoi S. Chem. Commun. 2016; 52: 9809
- 4l Zhang Q.-R, Huang J.-R, Zhang W, Dong L. Org. Lett. 2014; 16: 1684
- 4m Patureau FW, Glorius F. Angew. Chem. Int. Ed. 2011; 50: 1977
- 4n Petrova E, Rasina D, Jirgensons A. Eur. J. Org. Chem. 2017; 1773
- 4o Mo J, Wang L, Liu Y, Cui X. Synthesis 2015; 47: 439
- 4p Zheng L, Hua R. Chem. Eur. J. 2014; 20: 2352
- 5a Zhou HF, Fan QH, Tang WJ, Xu LJ, He YM, Deng GJ, Zhao LW, Gu LQ, Chan AS. C. Adv. Synth. Catal. 2006; 348: 2172
- 5b Sharma U, Kumar N, Verma PK, Kumar V, Singh B. Green Chem. 2012; 14: 2289
- 5c Kidwai M, Mishra NK, Bhardwaj S, Jahan A, Kumar A, Mozumdar S. ChemCatChem 2010; 2: 1312
- 5d Konda SG, Humne VT, Lokhande PD. Green Chem. 2011; 13: 2354
- 5e Zhao H, Cheng M, Zhang J, Cai M. Green Chem. 2014; 16: 2515
- 5f Fischmeister C, Doucet H. Green Chem. 2011; 13: 741
- 5g Cecchini MM, Charnay C, De Angelis F, Lamaty F, Martinez J, Colacino E. ChemSusChem 2014; 7: 45
- 5h Chen J, Spear SK, Huddleston JG, Rogers RD. Green Chem. 2005; 7: 64
- 5i Vafaeezadeh M, Hashemi MM. J. Mol. Liq. 2015; 207: 73
- 5j Li J.-H, Liu W.-J, Xie Y.-X. J. Org. Chem. 2005; 70: 5409
- 5k Burley GA, Davies DL, Griffith GA, Lee M, Singh K. J. Org. Chem. 2010; 75: 980
- 5l Chandrasekhar S, Narsihmulu C, Sultana SS, Reddy NR. Org. Lett. 2002; 4: 4399
- 6a Sawant D, Wagh Y, Bhatte K, Panda A, Bhanage B. Tetrahedron Lett. 2011; 52: 2390
- 6b Patil NM, Bhanage BM. ChemCatChem 2016; 8: 3458
- 6c Mane RS, Bhanage BM. Adv. Synth. Catal. 2017; 359: 2621
- 6d Gautam P, Bhanage BM. ChemistrySelect 2016; 1: 5463
- 6e Tiwari AR, Bhanage BM. Green Chem. 2016; 18: 144
- 7a Pineiro M, Dias LD, Damas L, Aquino GL.B, Calvete MJ. F, Pereira MM. Inorg. Chim. Acta 2017; 455: 364
- 7b Lidstrom P, Tierney J, Wathey B, Westman J. Tetrahedron 2001; 57: 9225
- 7c Strauss CR, Varma RS. In Microwave Methods in Organic Synthesis, Vol. 266. Larhed M, Olofssonq K. Springer; Berlin: 2006: 199
- 7d Martínez-Palou R. Mol. Diversity 2010; 14: 3
- 7e McBurney RT, Portela-Cubillo F, Walton JC. RSC Adv. 2012; 2: 1264
- 7f Dallinger D, Kappe CO. Chem. Rev. 2007; 107: 2563
- 7g Kaur N. Synth. Commun. 2015; 45: 1
- 8a The Chemistry and Biology of Isoquinoline Alkaloids . Phillipson JD, Roberts MF, Zenk MH. Springer Verlag; Berlin: 1985
- 8b Croisy-Delcey M, Croisy A, Carrez D, Huel C, Chiaroni A, Ducrot P, Bisagni E, Jin L, Leclercq G. Bioorg. Med. Chem. 2000; 8: 2629
- 8c Kashiwada Y, Aoshima A, Ikeshiro Y, Chen YP, Furukawa H, Itoigawa M, Fujioka T, Mihashi K, Cosentino LM, Morris-Natschke SL, Lee K.-H. Bioorg. Med. Chem. 2005; 13: 443
- 8d Reux B, Nevalainen T, Raitio KH, Koskinen AM. P. Bioorg. Med. Chem. 2009; 17: 4441
- 8e Khan AY, Kumar GS. Biophys. Rev. 2015; 7: 407
- 8f Giri P, Kumar GS. Mini-Rev. Med. Chem. 2010; 10: 568
- 8g Van Muijlwijk-Koezen JE, Timmerman H, Van Der Goot H, Menge WM. P. B, Von Drabbe Künzel JF, De Groote M, Jzerman AP. I. J. Med. Chem. 2000; 43: 2227
- 8h Kartsev VG. Med. Chem. Res. 2004; 13: 325
- 8i Bhadra K, Kumar GS. Med. Res. Rev. 2011; 31: 821
- 9a Fang K.-H.-Wu L.-L, Huang Y.-T, Yang C.-H, Sun I.-W. Inorg. Chim. Acta 2006; 359: 441
- 9b Sweetman BA, Müller-Bunz H, Guiry PJ. Tetrahedron Lett. 2005; 46: 4643
- 9c Bentley KW. Nat. Prod. Rep. 2006; 23: 444
- 9d Zhao Q, Liu S, Shi M, Wang C, Yu M, Li L, Li F, Yi T, Huang C. Inorg. Chem. 2006; 45: 6152
- 9e Park GY, Kim Y, Ha Y. Mol. Cryst. Liq. Cryst. 2007; 462: 179
- 9f Tsuboyama A, Iwawaki H, Furugori M, Mukaide T, Kamatani J, Igawa S, Moriyama T, Miura S, Takiguchi T, Okada S, Hoshino M, Ueno K. J. Am. Chem. Soc. 2003; 125: 12971
- 9g Chen Y, Sajjad M, Wang Y, Batt C, Nabi HA, Pandey RK. ACS Med. Chem. Lett. 2011; 2: 136
- 9h Lim CW, Tissot O, Mattison A, Hooper MW, Brown JM, Cowley AR, Hulmes DI, Blacker AJ. Org. Process Res. Dev. 2003; 7: 379
- 9i Pike VW, Halldin C, Crouzel C, Barré L, Nutt DJ, Osman S, Shah F, Turton DR, Waters SL. Nucl. Med. Biol. 1993; 20: 503
- 9j Skarydova L, Hofman J, Chlebek J, Havrankova J, Kosanova K, Skarka A, Hostalkova A, Plucha T, Cahlikova L, Wsol V. J. Steroid Biochem. Mol. Biol. 2014; 143: 250
- 10 Diaz G, Miranda IL, Diaz MA. N. In Phytochemicals - Isolation, Characterisation and Role in Human Health . Rao AV, Rao LG. IntechOpen Limited; London: 2015. Chap. 6
- 11a Gupta S, Han J, Kim Y, Lee SW, Rhee YH, Park J. J. Org. Chem. 2014; 79: 9094
- 11b Arambasic MJ, Hooper F, Willis MC. Org. Lett. 2013; 15: 5162
- 11c Pilgrim BS, Gatland AE, Esteves CH. A, McTernan CT, Jones GR, Tatton MR, Procopiou PA, Donohoe TJ. Org. Biomol. Chem. 2016; 14: 1065
- 11d Grigorjeva L, Daugulis O. Angew. Chem. Int. Ed. 2014; 53: 10209
- 11e Huang H, Li F, Xu Z, Cai J, Ji X, Deng G.-J. Adv. Synth. Catal. 2017; 359: 3102
- 12a Too PC, Wang Y.-F, Chiba S. Org. Lett. 2010; 12: 5688
- 12b Parthasarathy K, Cheng C.-H. J. Org. Chem. 2009; 74: 9359
- 12c Too PC, Chua SH, Wong SH, Chiba S. J. Org. Chem. 2011; 76: 6159
- 12d Zheng L, Ju J, Bin Y, Hua R. J. Org. Chem. 2012; 77: 5794
- 12e Zhang J, Qian H, Liu Z, Xiong C, Zhang Y. Eur. J. Org. Chem. 2014; 8110
- 12f Zhang X, Chen D, Zhao M, Zhao J, Jia A, Li X. Adv. Synth. Catal. 2011; 353: 719
- 12g Han W, Zhang G, Li G, Huang H. Org. Lett. 2014; 16: 3532
- 12h Liu W, Hong X, Xu B. Synthesis 2013; 45: 2137
- 12i Chuang S.-C, Gandeepan P, Cheng C.-H. Org. Lett. 2013; 15: 5750
- 12j Huang X.-C, Yang X.-H, Song R.-J, Li J.-H. J. Org. Chem. 2014; 79: 1025
- 12k Zhang S, Huang D, Xu G, Cao S, Wang R, Peng S, Sun J. Org. Biomol. Chem. 2015; 13: 7920
- 12l Wang Y.-F, Toh KK, Lee J.-Y, Chiba S. Angew. Chem. Int. Ed. 2011; 50: 5927
- 13a Wang J, Zha S, Chen K, Zhu J. Org. Chem. Front. 2016; 3: 1281
- 13b Muralirajan K, Kuppusamy R, Prakash S, Cheng C.-H. Adv. Synth. Catal. 2016; 358: 774
- 13c Wang H, Koeller J, Liu W, Ackermann L. Chem. Eur. J. 2015; 21: 15525
- 13d Sen M, Kalsi D, Sundararaju B. Chem. Eur. J. 2015; 21: 15529
- 13e Zhou S, Wang M, Wang L, Chen K, Wang J, Song C, Zhu J. Org. Lett. 2016; 18: 5632
- 13f Pawar AB, Agarwal D, Lade DM. J. Org. Chem. 2016; 81: 11409
- 14a Kornhaaß C, Li J, Ackermann L. J. Org. Chem. 2012; 77: 9190
- 14b Deshmukh DS, Bhanage BM. Org. Biomol. Chem. 2018; 16: 4864
- 15a Cheng H, Dong W, Dannenberg CA, Dong S, Guo Q, Bolm C. ACS Catal. 2015; 5: 2770
- 15b Yu Q, Hu L, Wang Y, Zheng S, Huang J. Angew. Chem. Int. Ed. 2015; 54: 15284
- 16 Deshmukh DS, Bhanage BM. Synlett 2018; 29: 979