One-Pot Synthesis of Indolo[2,3-c]quinolin-6-ones by Sequential Photocyclizations of 3-(2-Azidophenyl)-N-phenylacrylamides

Abstract

A one-pot synthesis of indolo[2,3-c]quinolin-6(7H)-ones was achieved by sequential photocyclizations of 3-(2-azidophenyl)-N-phenylacrylamides in moderate to high yields. The reactions proceeded via photochemical cyclization of aryl azides to form N-phenylindol-2-carbamides and subsequent 6π-electrocyclic reaction and oxidative aromatization to afford the corresponding indolo[2,3-c]quinolin-6(7H)-ones.

Key words

indolo[2,3-c]quinolin-6(7H)-ones - photocyclization - 3-(2-azidophenyl)-N-phenylacrylamides - aryl azides - 6π-electrocyclic reaction

• References and Notes



• 1a Cimanga K, De Bruyne T, Pieters L, Claeys M, Vlietinck A. Tetrahedron Lett. 1996; 37: 1703
• 1b Sharaf MH. M, Schiff PL, Tackie AN, Phoebe CH, Martin GE. J. Heterocycl. Chem. 1996; 33: 239
• 1c Pousset J.-L, Martin M.-T, Jossang A, Bodo B. Phytochemistry 1995; 39: 735
• 1d Kirby GC, Paine A, Warhurst DC, Noamese BK, Phillipson JD. Phytother. Res. 1995; 9: 359
• 2a Onyeibor O, Croft SL, Dodson HI, Feiz-Haddad M, Kendrick H, Millington NJ, Parapini S, Phillips RM, Seville S, Shnyder SD, Taramelli D, Wright CW. J. Med. Chem. 2005; 48: 2701
• 2b Lisgarten JN, Coll M, Portugal J, Wright CW, Aymami J. Nat. Struct. Biol. 2002; 9: 57
• 2c Wright CW, Addae-Kyereme J, Breen AG, Brown JE, Cox MF, Croft SL, Gökçek Y, Kendrick H, Phillips RM, Pollet PL. J. Med. Chem. 2001; 44: 3187
• 2d Bierer DE, Dubenko LG, Zhang P, Lu Q, Imbach PA, Garofalo AW, Phuan P.-W, Fort DM, Litvak J, Gerber RE, Sloan B, Luo J, Cooper R, Reaven GM. J. Med. Chem. 1998; 41: 2754
• 3a Van Miert S, Hostyn S, Maes BU. W, Cimanga K, Brun R, Kaiser M, Mátyus P, Dommisse R, Lemière G, Vlietinck A, Pieters L. J. Nat. Prod. 2005; 68: 674
• 3b Cimanga K, De Bruyne T, Lasure A, Van Poel B, Pieters L, Claeys M, Vanden Berghe D, Kambu K, Tona L, Vlietinck AJ. Planta Med. 1996; 62: 22
• 3c Cimanga K, De Bruyne T, Pieters L, Claeys M, Vlietinck A. Tetrahedron Lett. 1996; 37: 1703
• 3d Cimanga K, De Bruyne T, Pieters L, Vlietinck AJ, Turger CA. J. Nat. Prod. 1997; 60: 688
• 3e Grellier P, Ramiaramanana L, Millerioux V, Deharo E, Schrével J, Frappier F, Trigalo F, Bodo B, Pousset J.-L. Phytother. Res. 1996; 10: 317
• 4a Kadam HK, Parvatkar PT, Tilve SG. Synthesis 2012; 44: 1339
• 4b Parvatkar TP, Parameswaran SP, Tilve GS. Curr. Org. Chem. 2011; 15: 1036
• 4c Kraus GA, Guo H. Tetrahedron Lett. 2010; 51: 4137
• 4d Mori T, Ichikawa J. Synlett 2007; 1169
• 4e Amiri-Attou O, Terme T, Vanelle P. Synlett 2005; 3047
• 4f Fresneda PM, Molina P. Synlett 2004; 1
• 5a Fukushima K, Teller MN, Mountain IM, Tarnowski GS, Stock CC. J. Reticuloendoth. Soc. 1979; 26: 187
• 5b Grunberg E, Kramer MJ, Buck M, Trown PW. Chemotherapy 1978; 24: 77
• 6a Putey A, Popowycz F, Do Q.-T, Bernard P, Talapatra SK, Kozielski F, Galmarini CM, Joseph B. J. Med. Chem. 2009; 52: 5916
• 6b Hostyn S, Maes BU. W, Baelen GV, Gulevskaya A, Meyers C, Smits K. Tetrahedron 2006; 62: 4676
• 6c Vaillard VA, Budén ME, Martín SE, Rossi RA. Tetrahedron Lett. 2009; 50: 3829
• 6d Tokmakov GP, Zemlyanova TG, Grandberg II. Chem. Heterocycl. Comp. 1994; 30: 434
• 6e Kanaoka Y, Itoh K. Synthesis 1972; 36
• 7 Shi Z, Ren Y, Li B, Lu S, Zhang W. Chem. Commun. 2010; 46: 3973
• 8a Evans DA, Black WC. J. Am. Chem. Soc. 1993; 115: 4497
• 8b Sun K, Liu S, Bec PM, Driver TG. Angew. Chem. Int. Ed. 2011; 50: 1702
• 9a Ferrini S, Ponticelli F, Taddei M. J. Org. Chem. 2006; 71: 9217
• 9b Mayouf AM, Park Y.-T. J. Photochem. Photobiol. A: Chem. 2002; 150: 115
• 10a Winterfeldt E, Altmann HJ. Angew. Chem. 1986; 80: 486
• 10b Hoboken NJ. Org. React. (N. Y.) 1984; 30: 457
• 11 Typical Experimental Procedure: A solution 1a (128 mg, 0.5 mmol) in a mixture of anhyd benzene (54 mL) and anhyd CH₂Cl₂ (6 mL) was bubbled with oxygen for 10 min and irradiated at λ ≥280 nm with a medium-pressure mercury lamp (500 W) in three 25-mL Pyrex flasks at ambient temperature. The progress of reaction was monitored by TLC at regular intervals. After the solvent was removed under reduced pressure, the residue was separated by silica gel column chromatography eluted with hexane–EtOAc (5:1) to yield the product 3a. Selected spectroscopic data for compounds: 3a: pale yellow solid; mp 294–298 °C. IR (KBr): 3430, 3147, 2921, 1655, 1617, 735 cm^–1. ¹H NMR (400 MHz, DMSO): δ = 7.30–7.36 (m, 2 H), 7.41 (td, J = 8.4, 1.6 Hz, 1 H), 7.45–7.52 (m, 2 H), 7.64 (d, J = 8.0 Hz, 1 H), 8.45 (d, J = 8.0 Hz, 1 H). 8.48 (d, J = 8.4 Hz, 1 H), 11.86 (s, 1 H), 12.35 (s, 1 H). ¹³C NMR (100 MHz, DMSO): δ = 155.67, 138.81, 134.93, 127.59, 125.88, 125.62, 122.97, 122.31, 122.29, 122.22, 120.64, 118.17, 118.01, 116.06, 113.02. ESI–HRMS: m/z [M + H⁺] calcd for C₁₅H₁₁N₂O: 235.0871; found: 235.0870.
• 12a Rowe PA. S. C. D, Hansen DW. Tetrahedron Lett. 1983; 47: 5169
• 12b Kanaoka Y, Nakao S, Hatanaka Y. Heterocycles 1976; 261