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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.

SUBMITTER: Mane V

PROVIDER: S-EPMC6643647 | biostudies-literature | 2018 Dec

REPOSITORIES: biostudies-literature

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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.

Mane Vaijinath V Baiju Thekke V TV Namboothiri Irishi N N INN

ACS omega 20181218 12

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 elaborat ...[more]

PMID: 31458362

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