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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: shunsukentu.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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Mn(III)-Catalyzed Synthesis of Pyrroles from Vinyl Azides and 1,3-Dicarbonyl Compounds

Y.-F. Wang, K. K. Toh, S. Chiba, K. Narasaka, Org. Lett., 2008, 10, 5019-5022.


Key Words

Pyrroles, Vinyl Azides


ID: J54-Y2008-0210