Expedient Synthesis, on Large Scale, of Aliphatic Chaetomellic Anhydrides from N-Allyl-2,2-dichlorocarboxyamides

Abstract

Chaetomellic anhydride A and an analog (with two additional carbons) were obtained, on a preparative scale, starting from amides derived from the acylation of 2-(2-propenylamino)pyridine with 2,2-dichloropalmitic or 2,2-dichlorostearic acid. An alternative approach, in which the methyl substituent of the target anhydride is introduced by the carboxylic acid reactant and the long aliphatic chain is added through the allylamino moiety, proved unviable.

Keywords:

• Chaetomellic anhydride
• halocompounds
• lactams
• radical reactions

ACKNOWLEDGMENT

We thank the Ministero della Istruzione, Università e Ricerca (MIUR), for financial assistance.