Preparation of 3,5-bis(methylidene)-2,6-heptanedione and its application as a Michael acceptor

IF 2.1 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron Pub Date : 2025-05-17 DOI:10.1016/j.tet.2025.134731

Xixuan Zhao, Leyi Chang, Zilin Fang, Longchen Zhang, Shenghao Che, Sen Liang, Yongguo Liu, Baoguo Sun, Hongyu Tian, Ning Li

引用次数: 0

Abstract

A good Michael acceptor, 3,5-bis(methylidene)-2,6-heptanedione, was obtained in 31 % yield by the reaction of 2,4-pentanedione with formaldehyde derived from the decomposition of DMSO. Various primary amines underwent Michael addition with 3,5-bis(methylidene)-2,6-heptanedione, followed by intramolecular aldol condensation in a one-pot reaction to yield bicyclic products, N-substituted-8-methyl-3-azabicyclo[3.3.1]non-7-en-6-ones, with yields ranging from 32 % to 64 %. Reactions with sterically hindered amines resulted in bicyclic products with yields lower than 10 %, and reactions with aromatic amines did not yield the bicyclic products. The reaction of benzylthiol as a nucleophile gave 4,6-bis(benzylthiomethyl)-3-methyl-cyclohex-2-en-1-one with a yield of 47 %.

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3,5-二（亚甲基）-2,6-庚二酮的制备及其作为迈克尔受体的应用

2,4-戊二酮与DMSO分解产生的甲醛反应，以31%的产率得到了良好的Michael受体3,5-二（亚甲基）-2,6-庚二酮。各种伯胺与3,5-二（亚甲基）-2,6-庚二酮进行Michael加成反应，然后在一锅反应中进行分子内醛醇缩合，得到n-取代-8-甲基-3-氮杂环[3.3.1]非7-烯-6- 1双环产物，产率为32% ~ 64%。与位阻胺反应生成双环产物，产率低于10%，与芳香胺反应不生成双环产物。以苄基硫醇为亲核试剂，反应得到4,6-二（苄基硫甲基）-3-甲基-环己基-2-烯-1- 1，产率为47%。

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

Tetrahedron 化学-有机化学

CiteScore

3.90

自引率

4.80%

发文量

439

审稿时长

34 days

期刊介绍： Tetrahedron publishes full accounts of research having outstanding significance in the broad field of organic chemistry and its related disciplines, such as organic materials and bio-organic chemistry. Regular papers in Tetrahedron are expected to represent detailed accounts of an original study having substantially greater scope and details than that found in a communication, as published in Tetrahedron Letters. Tetrahedron also publishes thematic collections of papers as special issues and ''Reports'', commissioned in-depth reviews providing a comprehensive overview of a research area.