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通过环状磺酰胺亚胺与β,γ-不饱和α-酮羰基的多米诺反应,实现了金属和溶剂免费的方法来多样化取代的吡啶酸盐。

Metal- and Solvent-Free Approach to Diversely Substituted Picolinates via Domino Reaction of Cyclic Sulfamidate Imines with β,γ-Unsaturated α-Ketocarbonyls.

机构信息

Discipline of Chemistry, Indian Institute of Technology Indore , Simrol, Indore 453552, Madhya Pradesh, India.

出版信息

J Org Chem. 2017 Oct 20;82(20):10928-10938. doi: 10.1021/acs.joc.7b01792. Epub 2017 Oct 2.

Abstract

An efficient, solvent-free, and eco-friendly domino reaction of 5/6-membered cyclic sulfamidate imines with a variety of β,γ-unsaturated α-ketocarbonyls in neat conditions under MW irradiation promoted by DABCO as a solid organobase has been developed for the rapid construction of a novel class of densely functionalized picolinates. This interesting metal-solvent-free tactic allows a wide range of useful functionalities on the aryl rings and delivers good to excellent yields of the aforesaid aza-heterocycles within short time spans (20-40 min). A biologically promising imidazo[1,2-a]pyridine was successfully synthesized through our unique procedure.

摘要

一种高效、无溶剂、环保的多步串联反应,即在微波促进下,DABCO 作为固体有机碱,将 5/6 元环环状磺酰胺亚胺与各种β,γ-不饱和α-酮羰基化合物在 neat 条件下一锅反应,快速构建新型稠合功能化的吡啶酸盐。这种有趣的无金属-溶剂策略允许芳环上具有广泛的有用官能团,并在短时间内(20-40 分钟)以良好至优异的收率得到上述氮杂环化合物。通过我们独特的方法成功合成了具有生物应用前景的咪唑并[1,2-a]吡啶。

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