Synthesis of Cinnolines and Cinnolinium Salt Derivatives by Rh(III)-Catalyzed Cascade Oxidative Coupling/Cyclization Reactions

The Journal of Organic Chemistry
Yanwei WangBaiquan Wang

Abstract

A novel method for the synthesis of cinnolines and cinnolinium salt derivatives via Rh(III)-catalyzed cascade oxidative coupling/cyclization reaction from Boc-arylhydrazines and alkynes has been developed. The reactions have a broad substrate scope and high stereoselectivity with readily available starting materials and provides an efficient synthetic route for this kind of compounds. A catalytically competent five-membered rhodacycle has been isolated, thus revealing a key intermediate in the catalytic cycle.

References

Mar 13, 2003·Chemical Reviews·Douglas A HortonMark L Smythe
Feb 5, 2004·Bioorganic & Medicinal Chemistry·Alexander L RuchelmanEdmond J LaVoie
Apr 1, 1948·Journal of the American Chemical Society·E C KORNFELD
Nov 26, 2009·Bioorganic & Medicinal Chemistry Letters·C LunnissN Trivedi
Feb 8, 2011·Bioorganic & Medicinal Chemistry Letters·David A ScottXiaolan Zheng
Apr 19, 2011·Bioorganic & Medicinal Chemistry·Cristobal AlhambraMarc J Chapdelaine
Aug 14, 2012·Angewandte Chemie·Junichiro YamaguchiKenichiro Itami
Apr 5, 2013·Chemistry : a European Journal·Dongbing ZhaoJingsong You
Dec 23, 2014·Chemical Reviews·Xun-Xiang GuoWanbin Zhang
Apr 7, 2015·Accounts of Chemical Research·Guoyong Song, Xingwei Li
Nov 26, 2015·Chemistry, an Asian Journal·Parthasarathy Gandeepan, Chien-Hong Cheng
Jan 13, 2016·Organic & Biomolecular Chemistry·Sivakalai MayakrishnanParamasivan Thirumalai Perumal
Jan 14, 2016·Chemical Communications : Chem Comm·Yudong YangJingsong You
Jun 23, 2016·Angewandte Chemie·Moisés Gulías, José Luis Mascareñas
Nov 5, 2016·The Journal of Organic Chemistry·David SucunzaJuan J Vaquero
Jan 5, 2017·Chemical Reviews·Yoonsu ParkSukbok Chang
Nov 8, 2017·Accounts of Chemical Research·Xiaotian QiYu Lan
Jan 13, 2018·The Journal of Organic Chemistry·Min Hye Kim, Jinho Kim

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