甘氨酸催化回流条件下乙醇水溶液一锅三组分合成结构多样的2-氨基取代吡喃环杂环

IF 1.1 Q3 CHEMISTRY, MULTIDISCIPLINARY
B. Banerjee, M. Kaur, Aditi Sharma, Ashutosh Kumar Singh, A. Priya, V. Gupta, V. Jaitak
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引用次数: 5

摘要

在催化量的甘氨酸作为有效的无金属有机催化剂的存在下,芳香醛、丙二腈和各种C-H活化酸在乙醇水溶液中反应,在回流条件下,开发了一种简单、方便和通用的一锅三组分合成结构多样的2-氨基吡喃环杂环的方法。使用这种开发的方案,我们能够合成一系列结构多样的2-氨基吡喃衍生物,即2-氨基-4,5-二氢吡喃并[3,2-c]色烯、2-氨基-4、5-二氢吡喃并[4,3-b]吡喃、2-氨基-5,6,7,8-四氢-4H-色烯,2'-氨基-2,5'-二氧基-5'-H-螺[吲哚-3,4'-吡喃并[3,2-c]铬烯]-3'-腈和2'-氨基-1,3,5'-三氧代-1,3-二氢-5'-螺[茚-2,4'-吡喃并[3.2.c]铬烯]-3'-腈,产率优异。合成具有生物前景的吡喃和螺吡喃、高原子经济性、优异的产率、使用无金属催化剂、低毒溶剂、无色谱柱纯化、形成多个碳-碳和碳-杂原子键是这一新开发方案的一些主要优点。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
Glycine catalyzed one-pot three-component synthesis of structurally diverse 2-amino substituted pyran annulated heterocycles in aqueous ethanol under refluxed conditions
A facile, convenient and general method has been developed for the one-pot three-component synthesis of structurally diverse 2-amino pyran annulated heterocycles from the reactions of aromatic aldehydes, malononitrile and various C-H activated acids in the presence of a catalytic amount of glycine as an efficient metal-free organocatalyst in aqueous ethanol under refluxed conditions. Using this developed protocol, we were able to synthesize a series of structurally diverse 2-amino pyran derivatives viz., 2-amino-4,5-dihydropyrano[3,2-c]chromenes, 2-amino-4,5-dihydropyrano[4,3-b]pyrans, 2-amino-5,6,7,8-tetrahydro-4H-chromenes, 2'-amino-2,5'-dioxo-5'H-spiro[indoline-3,4'-pyrano[3,2-c]chromene]-3'-carbonitrile and 2'-amino-1,3,5'-trioxo-1,3-dihydro-5'H-spiro[indene-2,4'-pyrano[3,2-c]chromene]-3'-carbonitrile in excellent yields. Synthesis of biologically promising pyrans and spiropyrans, high atom economy, excellent yields, use of metal-free catalyst, less toxic solvents, no chromatographic column purifications, multiple carbon-carbon and carbon-heteroatom bond formations are some of the major advantages of this newly developed protocol.
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来源期刊
Current Green Chemistry
Current Green Chemistry CHEMISTRY, MULTIDISCIPLINARY-
CiteScore
4.30
自引率
13.60%
发文量
6
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