Zinc Chloride Catalyzed Amino Claisen Rearrangement of 1-N-Allylindolines: An Expedient Protocol for the Synthesis of Functionalized 7-Allylindolines

IF 1.3 3区化学 Q3 CHEMISTRY, ORGANIC

Heterocyclic Communications Pub Date : 2019-01-01 DOI:10.1515/hc-2019-0010

S. Jain

引用次数: 3

Abstract

Abstract 7-Allylindolines are valuable synthons for designing biologically active molecular libraries. Lewis acid catalyzed amino-Claisen rearrangement provides a one pot synthetic entry to these heteroarenes. In this context, Zinc chloride (ZnCl2)–N,N-dimethylformamide system efficiently catalyzed amino-Claisen rearrangements of 1-N-allylindolines to 7-allylindolines. The rearrangement is influenced by stereoelectronic effects of substituents present in 1-N-allylindolines. The substrates containing electron donating functionalities underwent rearrangement at lower temperature than substrates with electron withdrawing functional groups. The regioselectivity of the process is governed by the substitution pattern on allyl moiety in 1-N-allylindoline as well as ZnCl2 catalyst loading in the reaction system.

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氯化锌催化1-N-烯丙基吲哚的氨基克莱森重排反应：合成官能化7-烯丙基吲哚

摘要7-烯丙基吲哚是设计生物活性分子文库的有价值的合成子。路易斯酸催化的氨基克莱森重排为这些杂芳烃提供了一个一锅合成入口。在这种情况下，氯化锌（ZnCl2）–N，N-二甲基甲酰胺体系有效地催化了1-N-烯丙基吲哚啉的氨基克莱森重排为7-烯丙基吲哚。重排受到1-N-烯丙基吲哚中存在的取代基的立体电子效应的影响。与具有吸电子官能团的底物相比，含有给电子官能团的基质在较低的温度下发生重排。该方法的区域选择性由1-N-烯丙基吲哚中烯丙基部分的取代模式以及反应体系中ZnCl2催化剂的负载量决定。

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

Heterocyclic Communications 化学-有机化学

CiteScore

3.80

自引率

4.30%

发文量

审稿时长

1.4 months

期刊介绍： Heterocyclic Communications (HC) is a bimonthly, peer-reviewed journal publishing preliminary communications, research articles, and reviews on significant developments in all phases of heterocyclic chemistry, including general synthesis, natural products, computational analysis, considerable biological activity and inorganic ring systems. Clear presentation of experimental and computational data is strongly emphasized. Heterocyclic chemistry is a rapidly growing field. By some estimates original research papers in heterocyclic chemistry have increased to more than 60% of the current organic chemistry literature published. This explosive growth is even greater when considering heterocyclic research published in materials science, physical, biophysical, analytical, bioorganic, pharmaceutical, medicinal and natural products journals. There is a need, therefore, for a journal dedicated explicitly to heterocyclic chemistry and the properties of heterocyclic compounds.