Propylphosphonic acid anhydride–mediated amidation of Morita–Baylis–Hillman–derived indolizine-2-carboxylic acids. Issue 7 (July 2021)

• Record Type: Journal Article
• Authors: Sekgota, Khethobole C; Isaacs, Michelle; Hoppe, Heinrich C; Seldon, Ronnett; Warner, Digby F; Khanye, Setshaba D; Kaye, Perry T
• Is Part Of: Journal of chemical research. Volume 45:Issue 7/8(2021)
• Page Start: 674
• Page End: 678
• Publication Date: 2021-07
• Subjects: anti-mycobacterial -- carboxamide -- indolizine -- Morita–Baylis–Hillman -- propylphosphonic acid anhydride -- synthesis; Chemistry -- Research -- Periodicals; Chemistry -- Periodicals; 540.5
• DOI: 10.1177/1747519820987156
• Languages: English
• ISSNs: 1747-5198

Abstract

Propylphosphonic acid anhydride has been successfully used as a coupling agent in the synthesis of a series of indolizine-2-carboxamido derivatives from indolizine-2-carboxylic acid and its 3-acetylated analogue. The acid substrates were obtained by saponification of the corresponding methyl esters produced, in turn, selectively and efficiently, by time-controlled cyclisation of a single Morita–Baylis–Hillman adduct. Various amino and hydrazino compounds with medicinal potential have been used to prepare indolizine-2-carboxamido and hydrazido derivatives.