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[3+2] Cycloaddition of Propargylamines and α‐Acylketene Dithioacetals: A Synthetic Strategy for Highly Substituted Pyrroles
Author(s) -
Zhao YuLong,
Di ChongHui,
Liu SiDi,
Meng Jia,
Liu Qun
Publication year - 2012
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201200375
Subject(s) - cycloaddition , chemistry , amine gas treating , conjugate , combinatorial chemistry , organic chemistry , catalysis , mathematical analysis , mathematics
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.