A convenient and atom-economic one-pot SeCl2-mediated synthesis of 2-arylselenopheno[2,3-b]indoles and their antifungal activity

MARTINS, GUILHERME A. M.; KAUFMAN, TEODORO S.; DO CARMO, GABRIELE; SILVEIRA, CLAUDIO C.; MOREL, ADEMIR F.

Asian Journal of Organic Chemistry

Wiley

Lugar: Nueva York; Año: 2019 vol. 8 p. 369 - 375

A facile and convenient atom-economic protocolfor the one-pot synthesis of 2-aryl selenopheno[2,3-b]indoles,by an electrophilic cyclization of 3-(arylalkynyl)indoles withSeCl2 prepared in situ as the selenium source, is reported. Thetricyclic products were obtained in moderate to very goodyields. The reaction was optimized, and its scope andlimitations were systematically studied. It was observed thatits performance was affected by the steric and electronicproperties of the substituent attached to the nitrogen atomand to a lesser extent by the nature and position of thesubstituents of the pending aryl moiety. Halogen atomslocated para to the alkynyl group caused an average of 20%yield reduction. The reaction was unsuccessful with substratesbearing an alkyl chain attached to one of the sides ofthe alkynyl moiety. The antifungal activity of selected tricycliccompounds was tested against a panel of clinically relevantyeasts, and one of the heterocycles was exceptionallyeffective against Cryptococcus neoformans and C. Gatti.