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Paper | Special issue | Vol 80, No. 1, 2010, pp.251-258
Published online, 2nd February, 2009
DOI: 10.3987/COM-08-S(S)3
Synthesis of 4-Azachromeno[2,3-b]indol-11(6H)-one and Its Derivatives as Analogues of Ellipticine

Yanhong Chen, Chunhao Yang,* and Yuyuan Xie*

*State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, SIBS, Chinese Academy of Science, 555 Zu Chong Zhi Road, Shanghai 201203, China

Abstract

4-Azachromeno[2,3-b]indol-11(6H)-ones (4) and their derivatives (5) as analogues of ellipticine were synthesized through a straightforward, two or three-step process. Tetracyclic heterocycles (4) were obtained by facile cyclization of indolin-2-ones (2) or (3) and 2-chloronicotinoyl chloride under the condition of the ‘Jensen’-reaction. Alkylation of the compounds (4) afforded 6-substituted 4-azachromeno[2,3-b]indol-11(6H)-ones.