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通过偶极环加成-逆曼尼希多米诺反应合成吡咯并[1,3]二氮杂卓

Synthesis of pyrrolo[1,3]diazepines by a dipolar cycloaddition - retro-Mannich domino reaction.

作者信息

Liang Mary, Saiz Cecilia, Pizzo Chiara, Wipf Peter

机构信息

Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA.

出版信息

Tetrahedron Lett. 2009 Dec 1;50(49):6810-6813. doi: 10.1016/j.tetlet.2009.09.107.

DOI:10.1016/j.tetlet.2009.09.107
PMID:20160922
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC2770875/
Abstract

Microwave irradiation facilitated the synthesis of 4-arylthio-3-oxazolin-5-ones from ethyl cyanoformate, thiophenol, and cyclic ketones. Subsequent decarboxylation and in situ [3+2] cycloaddition provided novel 2,3,4,5-tetrahydro-1H-pyrrolo[1,2-c][1,3]diazepine scaffolds after a spontaneous retro-Mannich domino reaction.

摘要

微波辐射促进了由氰基甲酸乙酯、苯硫酚和环酮合成4-芳硫基-3-恶唑啉-5-酮。随后的脱羧反应和原位[3+2]环加成反应,在自发的逆曼尼希多米诺反应后提供了新型的2,3,4,5-四氢-1H-吡咯并[1,2-c][1,3]二氮杂卓骨架。