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

  • J Org Chem. 2018 Jan 19;83(2):843-853. doi: 10.1021/acs.joc.7b02831.
Vankudoth Jayaram  1 ,  Tailor Sridhar  1 ,  Gangavaram V M Sharma  1 ,  Fabienne Berrée  2 ,  Bertrand Carboni  2
Affiliations
  • 1. Organic and Biomolecular Chemistry Division, CSIR-Indian Institute of Chemical Technology , Tarnaka, Hyderabad-500 007, India.
  • 2. Univ Rennes, CNRS, ISCR (Institut des Sciences Chimiques de Rennes) - UMR 6226 , F-35000 Rennes, France.
PMID: 29251507 DOI: 10.1021/acs.joc.7b02831
Abstract

An efficient and straightforward synthesis of isoquinolines is reported from internal alkenyl boronic esters, easily prepared from the corresponding 1,2-bis(boronates), via a sequential copper-catalyzed azidation/aza-Wittig condensation. This synthetic method has been used to synthesize quinisocaine, a topical anesthetic used for the treatment of Pain and pruritus, and further extended to thieno[2,3-c]pyridines by using 2-thiophenecarboxaldehyde as coupling partner in the first step.

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