Regiodivergent cascade cyclization/alkoxylation of allenamides via N-protecting group driven rearrangement to access indole and indoline derivatives.

Autor:	Chaudhary D; Medicinal and Process Chemistry Division, CSIR-Central Drug Research Institute, Lucknow 226031, India. malleswara.kuram@cdri.res.in., Yadav S; Medicinal and Process Chemistry Division, CSIR-Central Drug Research Institute, Lucknow 226031, India. malleswara.kuram@cdri.res.in., Maurya NK; Medicinal and Process Chemistry Division, CSIR-Central Drug Research Institute, Lucknow 226031, India. malleswara.kuram@cdri.res.in.; Academy of Scientific and Innovative Research (AcSIR), Ghaziabad, 201002, India., Kumar D; Medicinal and Process Chemistry Division, CSIR-Central Drug Research Institute, Lucknow 226031, India. malleswara.kuram@cdri.res.in.; Academy of Scientific and Innovative Research (AcSIR), Ghaziabad, 201002, India., Ishu K; Medicinal and Process Chemistry Division, CSIR-Central Drug Research Institute, Lucknow 226031, India. malleswara.kuram@cdri.res.in., Kuram MR; Medicinal and Process Chemistry Division, CSIR-Central Drug Research Institute, Lucknow 226031, India. malleswara.kuram@cdri.res.in.; Academy of Scientific and Innovative Research (AcSIR), Ghaziabad, 201002, India.
Jazyk:	angličtina
Zdroj:	Chemical communications (Cambridge, England) [Chem Commun (Camb)] 2022 Oct 06; Vol. 58 (80), pp. 11300-11303. Date of Electronic Publication: 2022 Oct 06.
DOI:	10.1039/d2cc03174d
Abstrakt:	A mild, palladium-catalyzed domino Heck-cyclization/alkoxylation sequence of aryl halide tethered allenamides is described, providing regiodivergent indole and indoline derivatives controlled by the N-protecting group. This room temperature reaction provided a functionalizable olefinic moiety with broad substrate scope. Preliminary mechanistic studies support the rearrangement of an indoline-derived intermediate to indoles with the N -acetyl allenamides forming free (NH) indoles.
Databáze:	MEDLINE
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