Synthesis 2015; 47(19): 2961-2964
DOI: 10.1055/s-0034-1378861
special topic
© Georg Thieme Verlag Stuttgart · New York

Sonogashira Reaction of the Indolizine Ring

Ivan A. Shadrin
Moscow State University, Chemistry Department, Moscow, 119991, Russian Federation   Email: babaev@org.chem.msu.ru
,
Sergey A. Rzhevskii
Moscow State University, Chemistry Department, Moscow, 119991, Russian Federation   Email: babaev@org.chem.msu.ru
,
Victor B. Rybakov
Moscow State University, Chemistry Department, Moscow, 119991, Russian Federation   Email: babaev@org.chem.msu.ru
,
Eugene V. Babaev*
Moscow State University, Chemistry Department, Moscow, 119991, Russian Federation   Email: babaev@org.chem.msu.ru
› Author Affiliations
Further Information

Publication History

Received: 26 April 2015

Accepted after revision: 05 June 2015

Publication Date:
30 July 2015 (online)

Abstract

2-tert-Butyl-5-iodoindolizine underwent Sonogashira reaction with acetylenes in the presence of dichlorobis(triphenylphosphine)palladium, copper(I) iodide, and triethylamine in acetonitrile to give to the corresponding 5-ethynylindolizines in high yields; 5-iodo-2-phenylindolizine and 5-bromo-2-tert-butylindolizine did not undergo the reaction. Several structures were characterized by X-ray. The 5-ethynylindolizines did not undergo cyclization to give cycl[3.2.2]azines.

Supporting Information

 
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