无催化剂、三组分一锅法合成2-氨基-3-氰基-4H-吡喃类化合物

doi:10.11944/j.issn.1000-0518.2018.05.170220

摘要/Abstract

摘要：

4-H-吡喃类化合物在医药、化工、有机合成等方面应用广泛,因此,发展其有效的合成方法具有重要意义。本文主要研究无催化剂条件下,以水作为反应介质,乙醇作为辅助溶剂,促进芳香醛、丙二腈与多种1,3-二羰基化合物的三组分“一锅法”缩合反应,高产率地合成了3种超过50个2-氨基-3-氰基-4H-吡喃类化合物并进行了系统的结构表征。该方法具有反应条件温和、不使用催化剂、底物适用性广、反应和后处理过程简单以及环境友好等优点。

关键词: 多组分反应, 无催化剂, 水, 4H-吡喃, 绿色合成

Abstract:

4H-Pyrans and 4H-pyran-annulated heterocyclic scaffolds are the key building blocks of numerous natural products and represent a “drug-like” structural motif with a broad spectrum of applications in organic synthesis and medicinal chemistry. In this paper, a convenient one-pot three-component strategy was conducted successfully under catalyst-free condition employing water as reaction medium and ethanol as co-solvent. Three kinds, over fifty 2-amino-3-cyano-4H-pyran derivatives were synthesized in good to excellent yields by the condensation of a series of aromatic aldehydes with malononitrile and different 1,3-dicarbonyl compounds. Broad substrate scope, systematic characterization, eliminated catalyst, mild reaction condition, simple purification procedure are the best advantages in this methodology.

Key words: multi-component reaction, catalyst-free, water, 4H-pyran derivatives, green synthesis

吕乐, 毛胜雪, 李非, 朱小磊, 吕成伟. 无催化剂、三组分一锅法合成2-氨基-3-氰基-4H-吡喃类化合物[J]. 应用化学, 2018, 35(5): 518-525.

LÜ Yue, MAO Shengxue, LI Fei, ZHU Xiaolei, LÜ Chengwei. Efficient Synthesis of 2-Amino-3-cyano-4H-pyran Derivatives via Catalyst-Free One-Pot Tri-Component Reaction[J]. Chinese Journal of Applied Chemistry, 2018, 35(5): 518-525.

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