Synthesis of Bi-, Ter-, and Quaterpyridinecarboxylates via Propargylisoxazole-Pyridine Rearrangement

Ekaterina E Galenko; Mariya A Kryukova; Mikhail S Novikov; Alexander F Khlebnikov

doi:10.1021/acs.joc.0c00611

Synthesis of Bi-, Ter-, and Quaterpyridinecarboxylates via Propargylisoxazole-Pyridine Rearrangement

J Org Chem. 2020 May 1;85(9):6109-6122. doi: 10.1021/acs.joc.0c00611. Epub 2020 Apr 15.

Authors

Ekaterina E Galenko¹, Mariya A Kryukova¹, Mikhail S Novikov¹, Alexander F Khlebnikov¹

Affiliation

¹ Institute of Chemistry, Saint Petersburg State University, 7/9 Universitetskaya nab., St. Petersburg 199034, Russia.

PMID: 32264675
DOI: 10.1021/acs.joc.0c00611

Abstract

A flexible method was developed for the synthesis of 2,2'-bi-, 2,2':6',2″-ter-, and 2,2':6',2'':6'',2‴-quaterpyridines containing a nicotinic acid moiety. The approach involves the Fe(II)/Au(I)-catalyzed rearrangement of key 4-propargylisoxazole building blocks bearing a pyrid-2-yl or quinolin-2-yl substituent at the 3-position and Pd(0)-catalyzed cross-coupling reactions.