A straightforward, efficient indole synthesis based on thermolysis of 2-(2-azidobenzyl)furans with attack of the formed nitrene moiety onto the ipso position of furan ring has been developed. The cyclization is accompanied by furan ring opening and affords indoles with a 2-acylvinyl substituent suitable for further modifications.

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A Simple Route to Polysubstituted Indoles Exploiting Azide Induced Furan Ring Opening. -An efficient indole synthesis based on thermolysis of 2-(2-azidobenzyl)furans (III) and (VI) with attack of the formed nitrene moiety onto the ipso position of furan ring is developed. The cyclization is accompanied by furan ring opening and affords indoles with a 2-acylvinyl substituent (IV) and (VII) suitable for further modifications. -(ABAEV*, V. T.; PLIEVA, A. T.; CHALIKIDI, P. N.; UCHUSKIN, M. G.; TRUSHKOV, I. V.; BUTIN, A. V.; Org. Lett. 16 (2014) 16, 4150-4153, http://dx.