Selective Construction of Diverse Polycyclic Spirooxindoles via a Three-Component Reaction of Cyclic Mercapto-Substituted β‑Enamino Esters, Isatins, and Cyclic 1,3-Diketones

The three-component reaction of alkyl 2-(benzo­[b]­[1,4]­thiazin-3-ylidene)­acetates, isatins, and 1,3-indanedione (1,3-cyclopentanedione) in ethanol in the presence of acetic acid conveniently afforded spiro­[indeno­[1,2-b]­phenothiazine-6,3′-indolines] or spiro­[cyclopenta­[b]­phenothiazine-4,3′-i...

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Published in:Journal of organic chemistry 2020-10, Vol.85 (19), p.12117-12127
Main Authors: Sun, Quan-Shun, Sun, Jing, Pan, Liu-Na, Yan, Chao-Guo
Format: Article
Language:English
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Summary:The three-component reaction of alkyl 2-(benzo­[b]­[1,4]­thiazin-3-ylidene)­acetates, isatins, and 1,3-indanedione (1,3-cyclopentanedione) in ethanol in the presence of acetic acid conveniently afforded spiro­[indeno­[1,2-b]­phenothiazine-6,3′-indolines] or spiro­[cyclopenta­[b]­phenothiazine-4,3′-indolines] in good yields and with high diastereoselectivity. More interestingly, a similar three-component reaction with 4-hydroxychromen-2-one resulted in the unexpected polycyclic spiro­[benzo­[b]­chromeno­[3′,4′:5,6]­pyrano­[2,3-e]­[1,4]­thiazine-7,3′-indolines] in satisfactory yields. A plausible reaction mechanism was rationally proposed for formation of different kinds of the spiro compounds, and the stereochemistries of the various spiro compounds were clearly elucidated.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.0c01290