Synthesis of Polysubstituted N-H Pyrroles from Vinyl Azides and 1,3-Dicarbonyl Compounds
Shunsuke Chiba,* Yi-Feng Wang, Guillaume Lapointe and Koichi Narasaka*
*Division of Chemistry and Biological Chemistry, School of
Physical and Mathematical Sciences, Nanyang Technological University, Singapore
637371, Singapore, Email: shunsuke
ntu.edu.sg, narasakantu.edu.sg
S. Chiba, Y.-F. Wang, G. Lapointe, K. Narasaka, Org. Lett., 2008, 10, 313-316.
DOI: 10.1021/ol702727j (free Supporting Information)
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Abstract
Two methods for the regioselective synthesis of tetra- and trisubstituted N-H pyrroles from starting vinyl azides have been developed: A thermal pyrrole formation via the 1,2-addition of 1,3-dicarbonyl compounds to 2H-azirine intermediates generated in situ from vinyl azides and a Cu(II)-catalyzed synthesis with ethyl acetoacetate through a 1,4-addition.
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Key Words
ID: J54-Y2008-0210
