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Synthesis of Polysubstituted Isoquinolines and Related Fused Pyridines from Alkenyl Boronic Esters via a Copper-Catalyzed Azidation/Aza-Wittig Condensation Sequence

Vankudoth Jayaram, Tailor Sridhar, Gangavaram V. M. Sharma*, Fabienne Berrée and Bertrand Carboni*

*CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad-500 007, India; Univ Rennes, CNRS, ISCR, UMR 6226, F-35000 Rennes, France, Email: esmveeiict.res.in, bertrand.carboniuniv-rennes1.fr

V. Jaryaram, T. Sridhar, G. V. M. Sharma, F. Berrée, B. Carboni, J. Org. Chem., 2018, 83, 843-853.

DOI: 10.1021/acs.joc.7b02831 (free Supporting Information)


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Abstract

A sequential copper-catalyzed azidation/aza-Wittig condensation enables an efficient and straightforward synthesis of isoquinolines from internal alkenyl boronic esters, easily prepared from the corresponding 1,2-bis(boronates). This synthetic method has been used to synthesize quinisocaine, a topical anesthetic, and further extended to thieno[2,3-c]pyridines.

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Synthesis of Quinisocaine



Key Words

aza-Wittig reaction, isoquinolines


ID: J42-Y2018