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- Title
[3+2] Cycloaddition of Propargylamines and α-Acylketene Dithioacetals: A Synthetic Strategy for Highly Substituted Pyrroles.
- Authors
Zhao, Yu-Long; Di, Chong-Hui; Liu, Si-Di; Meng, Jia; Liu, Qun
- Abstract
A new [3+2] cycloaddition strategy for the direct synthesis of highly substituted pyrroles from the readily available α-acylketene dithioacetals (or related substrates) and commercially available propargylamines under mild metal-free conditions has been developed. In this reaction, the acyl group plays a critical role in driving the conjugate addition of propargylamine and further cyclization to give pyrroles. Furthermore, the wide scope was confirmed by the preparation of 1,2,3,4-tetrasubstituted pyrroles (60-70% yields) via a formal 1,2-acyl migrating [3+2] cycloaddition pathway with N-methylprop-2-yn-1-amine as the secondary amine component.
- Publication
Advanced Synthesis & Catalysis, 2012, Vol 354, Issue 18, p3545
- ISSN
1615-4150
- Publication type
Article
- DOI
10.1002/adsc.201200375