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碱促进4-重氮异苯并二氢吡喃-3-亚胺与二甲基锍叶立德的三组分环化反应:高官能化异苯并二氢吡喃并[4,3-]哒嗪的合成

Base Promoted Three-Component Annulation of 4-Diazoisochroman-3-imines with Dimethylsulfonium Ylides: Synthesis of Highly Functionalized Isochromeno[4,3-]pyridazines.

作者信息

Suleman Muhammad, Xie Jianwei, Wang Zaibin, Lu Ping, Wang Yanguang

机构信息

Department of Chemistry, Zhejiang University, Hangzhou, 310027, P. R. China.

出版信息

J Org Chem. 2021 Jan 1;86(1):455-465. doi: 10.1021/acs.joc.0c02204. Epub 2020 Dec 16.

Abstract

A novel method has been developed to synthesize a unique class of highly functionalized isochromeno[4,3-]pyridazines. This reaction features an intermolecular functionalization of terminal nitrogen atom of diazo group of 4-diazoisochoman-3-imine with two dimethylsulfonium ylide components, followed by a base promoted 6-exo-trig cyclization step. Readily available starting materials, a broad substrate scope, and operationally simple, mild, and catalyst-free reaction conditions are the prominent features of this method.

摘要

已开发出一种新颖的方法来合成一类独特的高官能化异色满并[4,3 -]哒嗪。该反应的特点是4 - 重氮异色满 - 3 - 亚胺重氮基团的末端氮原子与两个二甲硫鎓叶立德组分进行分子间官能化,随后进行碱促进的6 - 外向 - 环化步骤。该方法的突出特点是起始原料易于获得、底物范围广泛以及操作简单、温和且无催化剂的反应条件。

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