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: esmvee
iict.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
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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
