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无金属,一锅法对 para-苯醌甲叉的二醇 1,6-共轭加成,随后发生 ipso 环化:一种构建螺 1,4-二氧六环环己二烯酮衍生物的方法。

Metal free, one pot 1,6-Conjugate Addition of Diol on para-Quinone Methide followed by ipso cyclization: An Approach to Spiro 1,4-Dioxane cyclohexadienone Derivatives.

机构信息

Department of Chemistry, Savitribai Phule Pune University (Formerly University of Pune), Ganeshkhind, Pune, 411007, India.

出版信息

Chem Asian J. 2022 Dec 14;17(24):e202200931. doi: 10.1002/asia.202200931. Epub 2022 Nov 10.

Abstract

A novel one-pot transition metal-free and Brönsted acid mediated 1,6-conjugate addition of bisnuleophilic diol on biselectrophilc para-quinone methide followed by ipso cyclization assisted by NBS has been developed under mild reaction conditions, offers a new approach to synthesize spiro 1,4-dioxane cyclohexadienone derivatives. This strategy features broad substrate scope of p-QMs with high functional group tolerance and good yields of spirocyclic scaffolds (60-92 %). N-Bromo succinimide an important role in an ipso spirocyclization with high efficiency.

摘要

发展了一种在温和反应条件下,通过新型一锅法、无过渡金属和布朗斯特酸催化,双亲核二醇对双亲电试剂对醌甲亚胺的 1,6-共轭加成,随后在 N-溴代琥珀酰亚胺(NBS)的协助下进行直接环化的反应,为合成螺 1,4-二氧六环环己二烯酮衍生物提供了一种新方法。该策略具有广泛的 p-QM 底物范围,对官能团具有高耐受性,螺环骨架的收率也很高(60-92%)。N-溴代琥珀酰亚胺在高效的反式螺环化反应中起着重要作用。

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