Multiheterocyclic Motifs via Three-Component Reactions of Benzynes, Cyclic Amines, and Protic Nucleophiles

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2017-12-14 DOI:10.1021/acs.orglett.7b03458

Sean P. Ross, Thomas R. Hoye*

引用次数: 21

Abstract

A broadly general, three-component reaction strategy for the construction of compounds containing multiple heterocycles is described. Thermal benzyne formation (by the hexadehydro-Diels–Alder (HDDA) reaction) in the presence of tertiary cyclic amines and a protic nucleophile (HNu) gives, via ring-opening of intermediate ammonium ion/Nu^– ion pairs, heterocyclic products. Many reactions are efficient even when the stoichiometric loading of the three reactants approaches unity. Use of HOSO₂CF₃ as the HNu gives ammonium triflate intermediates, which can then be ring opened by an even wider variety of nucleophiles.

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苯、环胺和亲核试剂三组分反应中的多杂环基序

描述了一种广泛通用的三组分反应策略，用于构建含有多个杂环的化合物。在叔环胺和亲核试剂(HNu)的存在下(通过六氢- diels - alder (HDDA)反应)生成热苯，通过中间铵离子/努离子对开环生成杂环产物。许多反应即使在三种反应物的化学计量负荷接近统一时也是有效的。使用HOSO2CF3作为HNu产生三酸铵中间体，然后可以被更广泛的亲核试剂开环。

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.