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通过炔基芳醛的亲电环化反应合成异色烯和萘。

Syntheses of isochromenes and naphthalenes by electrophilic cyclization of acetylenic arenecarboxaldehydes.

作者信息

Yue Dawei, Della Ca Nicola, Larock Richard C

机构信息

Department of Chemistry, Iowa State University, Ames, Iowa 50011, USA.

出版信息

J Org Chem. 2006 Apr 28;71(9):3381-8. doi: 10.1021/jo0524573.

DOI:10.1021/jo0524573
PMID:16626117
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC2586152/
Abstract

Highly substituted 1H-isochromenes, isobenzofurans, and pyranopyridines can be prepared by allowing o-(1-alkynyl)arenecarboxaldehydes and ketones to react with I2, ICl, NIS, Br2, NBS, p-O2NC6H4SCl, or PhSeBr and various alcohols or carbon-based nucleophiles at room temperature. Naphthyl ketones and iodides are also readily prepared by the reaction of 2-(1-alkynyl)arenecarboxaldehydes with I2 and simple olefins or alkynes.

摘要

高度取代的1H-异苯并呋喃、异苯并呋喃和吡喃并吡啶可通过使邻（1-炔基）芳醛和酮与I2、ICl、NIS、Br2、NBS、对硝基苯磺酰氯或苯硒溴以及各种醇或碳基亲核试剂在室温下反应来制备。萘基酮和碘化物也可通过2-（1-炔基）芳醛与I2和简单烯烃或炔烃的反应轻松制备。

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Synthesis of highly substituted furans by the electrophile-induced coupling of 2-(1-alkynyl)-2-alken-1-ones and nucleophiles.通过亲电试剂诱导的2-(1-炔基)-2-烯-1-酮与亲核试剂的偶联反应合成高度取代的呋喃。
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