Synthesis of Spiro- and Fused Heterocycles via (4+4) Annulation of Sulfonylphthalide witho-Hydroxystyrenyl Derivatives

Suresh, Alati ; Baiju, Thekke V. ; Kumar, Tarun ; Namboothiri, Irishi N. N. (2019) Synthesis of Spiro- and Fused Heterocycles via (4+4) Annulation of Sulfonylphthalide witho-Hydroxystyrenyl Derivatives Journal of Organic Chemistry, 84 (6). pp. 3158-3168. ISSN 0022-3263

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Official URL: http://doi.org/10.1021/acs.joc.8b03039

Related URL: http://dx.doi.org/10.1021/acs.joc.8b03039

Abstract

An expedient one-pot protocol for the synthesis of functionalized benzofuran containing fused and spiro-heterocycles has been accomplished by the modified Hauser–Kraus (HK) annulation of sulfonylphthalide with o-hydroxychalcones and o-hydroxynitrostyrylisoxazoles. The multicascade process involves Michael addition, Dieckmann cyclization, and a series of cyclizations, eliminations, and rearrangements to deliver the fused and spiro-heterocyclic products. An unusual transformation of fused indenofuran to naphthoquinone, the classical HK adduct, unraveled a novel pathway for the synthesis unsymmetrical naphthoquinones.

Item Type:Article
Source:Copyright of this article belongs to American Chemical Society.
Keywords:Cyclization; Silica,Chemical Reactions; Annulations, Reactivity.
ID Code:121312
Deposited On:14 Jul 2021 09:10
Last Modified:14 Jul 2021 09:10

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