A Facile, Superacid-Promoted Sequential Domino One-Pot Dual C–C Bond Formation and Fischer Indole Synthesis: Rapid Access to 10-Phenyl-5,10-dihydroindeno[1,2-b]indoles

Abstract

A superacid-promoted sequential domino one-pot approach for the synthesis of novel 10-phenyl-5,10-dihydroindeno[1,2-b]indoles, ubiquitous core structure present in many alkaloid natural products, is presented. The entire sequential process involves a domino intermolecular Friedel–Crafts alkylation and intramolecular acylation of simple and easily accessible ethyl cinnamates, to furnish the corresponding indanones, followed by the Fischer indole reaction. Interestingly, this method enabled the synthesis of various dihydroindeno[1,2-b]indoles possessing tertiary or quaternary centers at the 10th position.

Key words

cinnamates - arenes - Friedel–Crafts reaction - Fischer indole synthesis - indoles - fused-ring systems

• References

• 1 Friedel C, Crafts JM. C. R. Hebd. Seances Acad. Sci. 1877; 84: 1450
• 2a Fischer E, Jourdan F. Ber. Dtsch. Chem. Ges. 1883; 16:  2241
• 2b Fischer E, Hess O. Ber. Dtsch. Chem. Ges. 1884; 17: 559
• 3a Sundberg RJ. The Chemistry of Indoles . Academic; New York: 1970
• 3b Zaimoku H, Taniguchi T, Ishibashi H. Org. Lett. 2012; 14: 1656
• 3c Humphrey GR, Kuethe JT. Chem. Rev. 2006; 106: 2875
• 3d Shiri M, Zolfigol MA, Kruger HG, Tanbakouchian Z. Chem. Rev. 2010; 110: 2250
• 3e Hibino S, Chozi T. Nat. Prod. Rep. 2001; 18: 66
• 3f Gribble GW. J. Chem. Soc., Perkin Trans. 1 2000; 1045
• 3g Kenda B, Quesnel Y, Ates A, Michel P, Turet L, Mercier J. WO2006128693, 2006
• 4a Hammartstrom M, Venemalm L, Bergman J, Eneroth P. Am. J. Chin. Med. 1990; 18: 1
• 4b Wenkert E, Moeller PD. R, Piettre SR. J. Org. Chem. 1988; 53: 3170
• 5a Campos KR, Journet M, Lee S, Grabowski EJ. J, Tillyer RD. J. Org. Chem. 2005; 70: 268
• 5b Sturino CF, O’Neill G, Lachance N, Boyd M, Berthelette C, Labelle M, Li L, Roy B, Scheigetz J, Tsou N. J. Med. Chem. 2007; 50: 794
• 6 Maynart G, Pousset JL, Mboup S, Denis F. C. R. Seances Soc. Biol. Ses Fil. 1980; 174: 925
• 7a Springer JP, Clardy J. Tetrahedron Lett. 1980; 21: 231
• 7b Smith AB, Mewshaw R. J. Am. Chem. Soc. 1985; 107: 1769
• 8a Lewis SE. Tetrahedron 2006; 62: 8655
• 8b Higuchi T, Kawasaki T. Nat. Prod. Rep. 2007; 24: 843
• 8c Lounasmaa M, Tolvanen A. Nat. Prod. Rep. 2000; 17: 175
• 8d Rongved P, Kirsch G, Bouaziz Z, Jose J, Le Borgne M. Eur. J. Med. Chem. 2013; 69: 465
• 8e Graham J, Ninan A, Reza K, Sainsbury M, Shertzer HG. Tetrahedron 1992; 48: 167
• 8f Brown DW, Mahon MF, Ninan A, Sainsbury M, Shertzer HG. Tetrahedron 1993; 49: 8919
• 8g Abbiati G, Canevari V, Rossi E, Ruggeri A. Synth. Commun. 2005; 35: 1845
• 8h Baran PS, Richter JM. J. Am. Chem. Soc. 2005; 127: 15394
• 8i Barolo SM, Rosales C, Guio JE. A, Rossi RA. J. Heterocycl. Chem. 2006; 43: 695
• 9a Jewett JC, Sletten EM, Bertozzi CR. J. Am. Chem. Soc. 2010; 132: 3688
• 9b Jewett JC, Bertozzi CR. Org. Lett. 2011; 13: 5937
• 10 Kashyap M, Kandekar S, Baviskar AT, Das D, Preet R, Mohapatra P, Satapathy SR, Siddharth S, Guchhait SK, Kundu CN, Banerjee UC. Bioorg. Med. Chem. Lett. 2013; 23: 934
• 11 Kashyap M, Das D, Preet R, Mohapatra P, Satapathy SR, Siddharth S, Kundu CN, Guchhait SK. Bioorg. Med. Chem. Lett. 2012; 22: 2474
• 12 Talaz O, Gülçin I, Göksu S, Saracoglu N. Bioorg. Med. Chem. 2009; 17: 6583
• 13a Ferreira EM, Stoltz BM. J. Am. Chem. Soc. 2003; 125: 9578
• 13b Venkatesh C, Singh PP, Ila H, Junjappa H. Eur. J. Org. Chem. 2006; 5378
• 13c Balskus EP, Walsh CT. J. Am. Chem. Soc. 2009; 131: 14648
• 13d Yadav AK, Peruncheralathan S, Ila H, Junjappa H. J. Org. Chem. 2007; 72: 1388
• 13e Tseng N.-W, Lautens M. J. Org. Chem. 2009; 74: 1809
• 13f Chen B, Fan W, Chai G, Ma S. Org. Lett. 2012; 14: 3616
• 13g Saito K, Sogou H, Suga T, Kusama H, Iwasawa N. J. Am. Chem. Soc. 2011; 133: 689
• 13h Xu B, Guo Z.-L, Jin W.-Y, Wang Z.-P, Peng Y.-G, Guo Q.-X. Angew. Chem. Int. Ed. 2012; 51: 1059; Angew. Chem. 2012, 124, 1083
• 13i Chu X.-Q, Zi Y, Lu X.-M, Wang S.-Y, Ji S.-J. Tetrahedron 2014; 70: 232
• 13j Inman M, Moody CJ. Chem. Commun. 2011; 47: 788
• 13k Chernyak N, Tilly D, Li Z, Gevorgyan V. Chem. Commun. 2010; 46: 150
• 13l Ma Y, You J, Song F. Chem. Eur. J. 2013; 19: 1189
• 13m Brown RF. C, Coulston KJ, Eastwood FW, Moffat MR. Tetrahedron 1992; 48:  7763
• 14a Jiang B, Li Q.-Y, Tu S.-J, Li G. Org. Lett. 2012; 14: 5210
• 14b Yokosaka T, Nakayama H, Nemoto T, Hamada Y. Org. Lett. 2013; 15: 2978
• 14c Dethe DH, Erande RD, Ranjan A. J. Am. Chem. Soc. 2011; 133: 2864
• 14d Dethe DH, Erande RD, Ranjan A. J. Org. Chem. 2013; 78: 10106
• 14e Gore S, Baskaran S, König B. Org. Lett. 2012; 14: 4568
• 15a Reddy AG. K, Satyanarayana G. Tetrahedron 2012; 68: 8003
• 15b Mahendar L, Krishna J, Reddy AG. K, Ramulu BV. Org. Lett. 2012; 14: 628
• 15c Reddy AG. K, Krishna J, Satyanarayana G. Tetrahedron Lett. 2012; 53: 5635
• 15d Reddy AG. K, Krishna J, Satyanarayana G. Tetrahedron 2013; 69: 10098
• 15e Mahendar L, Satyanarayana G. J. Org. Chem. 2014; 79: 2059
• 15f Krishna J, Reddy AG. K, Satyanarayana G. Synlett 2013; 24: 967
• 15g Krishna J, Reddy AG. K, Satyanarayana G. Tetrahedron Lett. 2014; 55: 861
• 16 Ramulu BV, Reddy AG. K, Satyanarayana G. Synlett 2013; 24: 868
• 17a Walspurger S, Vasilyev AV, Sommera J, Palec P. Tetrahedron 2005; 61: 3559
• 17b Rudenko AP, Aristov SA, Vasilyev AV. Russ. J. Org. Chem. 2004; 40: 1221
• 17c Alkhafaji HM. H, Vasilyev AV, Ryabukhin DS, Rudenko AP, Muzalevskiy VM, Nenajdenko VG. Russ. J. Org. Chem. 2013; 49: 621
• 18 CCDC 990792 contains the supplementary crystallographic data for compound 13l in this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.