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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

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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https://hal-univ-rennes1.archives-ouvertes.fr/hal-01709528
Contributor : Laurent Jonchère <>
Submitted on : Friday, April 27, 2018 - 11:19:42 AM
Last modification on : Thursday, March 5, 2020 - 2:05:57 PM
Long-term archiving on: : Thursday, September 20, 2018 - 5:46:15 AM

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Vankudoth Jayaram, Tailor Sridhar, Gangavaram V. M. Sharma, Fabienne Berrée, Bertrand Carboni. Synthesis of Polysubstituted Isoquinolines and Related Fused Pyridines from Alkenyl Boronic Esters via a Copper-Catalyzed Azidation/Aza-Wittig Condensation Sequence. Journal of Organic Chemistry, American Chemical Society, 2018, 83 (2), pp.843-853. ⟨10.1021/acs.joc.7b02831⟩. ⟨hal-01709528⟩

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