SPONTANEOUS FORMATION OF TRICYCLIC LACTONES FOLLOWING THE CASTAGNOLI–CUSHMAN REACTION

Authors

  • Liliia Usmanova Institute of Chemistry, Saint Petersburg State University, 26 Universitetskii Ave., Peterhof 198504
  • Olga Bakulina Institute of Chemistry, Saint Petersburg State University, 26 Universitetskii Ave., Peterhof 198504
  • Dmitry Dar'in Institute of Chemistry, Saint Petersburg State University, 26 Universitetskii Ave., Peterhof 198504
  • Mikhail Krasavin Institute of Chemistry, Saint Petersburg State University, 26 Universitetskii Ave., Peterhof 198504

DOI:

https://doi.org/10.1007/3676

Keywords:

tricyclic lactones-lactams, Castagnoli–Cushman reaction, intramolecular SNAr reaction, post-MCR modification

Abstract

Castagnoli–Cushman reaction of imines derived from 2-chloropyridine-3-carboxaldehyde with a cyclic anhydride (4-(methylsulfonyl)morpholine-2,6-dione) conducted at 110°C in DMF over 1 h, as expected, led to a mixture of trans- and cis-configured carboxylic acids. However, the latter underwent a spontaneous intramolecular reaction of the carboxylic functionality onto the labile nearby 2-chloropyridine moiety to give the respective tricyclic lactones in 17–23% yield, along with 41–68% yield of the uncyclized transconfigured products (isolated as methyl esters).

Downloads

Published

2017-05-09

Issue

Vol. 53 No. 4 (2017): Multicomponent reactions in the synthesis of heterocycles

Section

Original Papers