Spontaneous formation of tricyclic lactones following the Castagnoli–Cushman reaction

Research output

Abstract

[Figure not available: see fulltext.] 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 trans-configured products (isolated as methyl esters).

Original languageEnglish
Pages (from-to)474-479
Number of pages6
JournalChemistry of Heterocyclic Compounds
Volume53
Issue number4
DOIs
Publication statusPublished - 1 Apr 2017

Scopus subject areas

  • Organic Chemistry

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