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钯催化的 N-对甲苯磺酰基氮丙啶和 2-碘代噻酚的串联环开/羧酰胺化反应:一种制备 1,4-苯并噻嗪-5-酮的简便高效方法。

Palladium-catalyzed domino ring-opening/carboxamidation reactions of N-tosyl aziridines and 2-iodothiophenols: a facile and efficient approach to 1,4-benzothiazepin-5-ones.

机构信息

Centre for Catalysis Research and Innovation, Department of Chemistry, University of Ottawa, 10 Marie Curie, Ottawa, Ontario, Canada, K1N 6N5.

出版信息

Org Lett. 2010 Dec 3;12(23):5567-9. doi: 10.1021/ol102394h. Epub 2010 Nov 4.

DOI:10.1021/ol102394h
PMID:21049948
Abstract

A novel and efficient domino procedure has been developed for the synthesis of 1,4-benzothiazepin-5-ones from simple and readily accessible N-tosyl aziridines and o-iodothiophenols. This process involves aziridines ring-opening with o-iodothiophenols, followed by palladium-catalyzed intramolecular carboxamidation. The scope and limitation of this transformation have been investigated in detail by using various aziridines and o-iodothiophenols.

摘要

一种新颖、高效的多米诺反应过程已经被开发出来,用于从简单易得的 N-对甲苯磺酰基氮丙啶和邻碘代硫酚合成 1,4-苯并硫氮杂卓-5-酮。该过程涉及氮丙啶与邻碘代硫酚开环,随后进行钯催化的分子内羧酰胺化反应。通过使用各种氮丙啶和邻碘代硫酚,详细研究了这种转化的范围和限制。

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