Synthesis of Functionalized Thieno[2,3-b]indoles via One-Pot Reaction of Indoline-2-thiones with Morita-Baylis-Hillman and Rauhut-Currier Adducts of Nitroalkenes.

Abstract

A straightforward protocol for the synthesis of functionalized thieno[2,3-b]indoles by base-mediated [3 + 2]-annulation of indoline-2-thione with Morita–Baylis–Hillman and Rauhut–Currier adducts of nitroalkenes is described. Complete regioselectivity, broad substrate scope, and mild reaction conditions make this strategy very valuable. Moreover, the thieno[2,3-b]indoles comprising functional groups such as hydrazine and ketoalkyl moieties are amenable for further synthetic elaboration.