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Gold-Catalyzed 1,2-Migration of Silicon, Tin, and Germanium en Route to C-2 Substituted Fused Pyrrole-Containing Heterocycles

Ilya V. Seregin and Vladimir Gevorgyan*

*Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607-7061, Urbana, IL 61801, Email: vladuic.edu

I. V. Seregin, V. Gevorgyan, J. Am. Chem. Soc., 2006, 128, 12050-12051.

DOI: 10.1021/ja063278l (free Supporting Information)


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Abstract

An Au-catalyzed synthesis of fused pyrroloheterocycles from diverse propargyl-substituted heterocycles proceeds via alkyne-vinylidene isomerization with concomitant 1,2-shift of hydrogen, silyl, germyl, and stannyl groups. This method allows for mild and efficient synthesis of diverse C-2 substituted N-heterocycles.

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Two-Component Approach Toward a Fully Substituted N-Fused Pyrrole Ring

D. Chernyak, C. Skontos, V. Gevorgyan, Org. Lett., 2010, 12, 3242-3245.

Low Temperature Organocopper-Mediated Two-Component Cross Coupling/Cycloisomerization Approach Toward N-Fused Heterocycles

D. Chernyak, S. B. Gadamsetty, V. Gevorgyan, Org. Lett., 2008, 10, 2307-2310.


Key Words

benzo-fused N-Heterocycles, Indolizines


ID: J48-Y2006-3100