Catalytic Cycloisomerization–Oxidative Cyclization Reaction Sequence of Enyne Diesters Derived from 2-Propargyloxyarylaldehydes

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2024-11-07 DOI:10.1021/acs.orglett.4c0385610.1021/acs.orglett.4c03856

Karmdeo Prajapati, Manoj Kumar Saini, Rajesh G. Gonnade and Ashok K. Basak*,

引用次数: 0

Abstract

Enyne diesters derived from 2-propargyloxyarylaldehydes are converted into 2-oxopyranochromenes via In(OTf)₃-catalyzed cycloisomerization and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ)-mediated oxidative cyclization reaction sequence in one pot. The process possesses broad substrate scope and good functional group compatibility and generates various 4-(hetero)aryl-substituted 2-oxopyranochromenes in 32–79% yields (over two steps). 2-Oxopyranochromenes undergo selective decarboxylation under Krapcho conditions. When treated with aliphatic secondary amines in DMF, 2-oxopyranochromenes undergo decarboxylative amination at ambient temperature to generate 2-amino-substituted functionalized chromenes in good yields.

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2-Propargyloxyaryldealhydes 衍生的炔二酯的催化环异构化-氧化环化反应序列

通过 In(OTf)3 催化的环异构化反应和 2,3-二氯-5,6-二氰基-1,4-苯醌 (DDQ) 介导的氧化环化反应顺序，在一锅内将 2-丙炔氧基芳醛衍生的炔二酯转化为 2-氧代吡喃色烯。该工艺具有广泛的底物范围和良好的官能团兼容性，可生成各种 4-（杂）芳基取代的 2-氧代吡喃色烯，收率为 32-79%（分两步进行）。在 Krapcho 条件下，2-氧代吡喃苯并吡喃会发生选择性脱羧反应。当在 DMF 中用脂肪族仲胺处理时，2-氧代吡喃苯并吡喃会在常温下发生脱羧胺化反应，生成 2-氨基取代的官能化苯并吡喃，收率很高。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.