Synthesis 2020; 52(05): 719-726
DOI: 10.1055/s-0039-1691492
paper
© Georg Thieme Verlag Stuttgart · New York

Palladium-Catalyzed Oxidative Annulation of Pyrrolylalkyl-1H-azoles: Towards the Synthesis of Polyheterocyclic Arenes

Krishna N. Tripathi
a  Department of Chemistry, Indian Institute of Technology Delhi, Hauz Khas, New Delhi 110016, India   Email: ravips@chemistry.iitd.ac.in
,
Avinash H. Bansode
b  Division of Organic Chemistry, National Chemical Laboratory, Dr. Homi Bhabha Road, Pune 411008, India
,
Ravi P. Singh
a  Department of Chemistry, Indian Institute of Technology Delhi, Hauz Khas, New Delhi 110016, India   Email: ravips@chemistry.iitd.ac.in
› Author Affiliations
We are grateful for the generous financial support from the Science and Engineering Research Board, DST-India (EMR/2017/000319), the Council of Scientific and Industrial Research (CSIR), India [02(0254)/16/EMR-II], and the Board of Research in Nuclear Sciences, DAE (58/1408/2019-BRNS/10377).
Further Information

Publication History

Received: 17 October 2019

Accepted after revision: 01 November 2019

Publication Date:
27 November 2019 (online)


Abstract

A highly efficient and regioselective palladium-catalyzed annulation protocol for a series of linear and terminally substituted 1,2- and 1,3-di(heteroaryl)alkanes to the corresponding polyheterocyclic arenes is reported. Herein, intramolecular oxidative coupling involving double C(sp2)–H bond functionalization provides a feasible access to biheteroaryl systems annulated to a six-membered ring. The methodology is not restricted to six-membered annulations and was extended to the synthesis of compounds with a seven-membered ring and biheteroaryl core.

Supporting Information

 
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