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
Author(s) -
Vaijinath Mane,
Thekke V. Baiju,
Irishi N. N. Namboothiri
Publication year - 2018
Publication title -
acs omega
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.779
H-Index - 40
ISSN - 2470-1343
DOI - 10.1021/acsomega.8b02147
Subject(s) - indoline , baylis–hillman reaction , adduct , chemistry , morita therapy , organic chemistry , medicinal chemistry , mathematics , pure mathematics
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.
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