An Expeditious Synthesis of Chiral 1, 2, 4‐Oxadiazole Peptidomimetics from Heteroaroyl Monopeptides. Issue 39 (22nd October 2018)

• Record Type: Journal Article
• Authors: Purushotham, Nikil; Poojary, Boja
• Is Part Of: ChemistrySelect. Volume 3:Issue 39(2018)
• Page Start: 10996
• Page End: 10998
• Publication Date: 2018-10-22
• Subjects: Amidoximes -- heteroaroyl monopeptide -- O-acylation -- 1, 2, 4-oxadiazole -- peptidomimetics; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/slct.201801921
• Languages: English
• ISSNs: 2365-6549

Abstract

Abstract: Amino acid derived amide bond bioisosteric peptidomimetics, such as 1, 2, 4‐oxadiazoles are generally prepared by two‐step processes as demonstrated well in the literature. There have been no reports on the synthesis of 1, 2, 4‐oxadiazoles from heteroaroyl peptides in a single step to date. In our work, 1, 2, 4‐oxadiazole peptidomimetics were synthesized efficiently via one‐pot cyclodehydration of O ‐acyl amidoximes engendered in situ, from heteroaroyl monopeptides and aryl or benzyl amidoximes with up to 93% yield. The process utilized DCC as the activating agent and did not considerably affect the conversion with the variation of amidoximes or monopeptides. Hence, the process could be useful in the design and synthesis of novel 1, 2, 4‐oxadiazole peptidomimetic based therapeutics. Abstract : A convenient N, N ′‐dicyclohexylcarbodiimide mediated successive O ‐acylation of benzo/benzyl amidoximes with heteroaroyl monopeptides followed by a cyclodehydration reaction leading to 1, 2, 4‐oxadiazole peptidomimetics was developed in one‐pot fashion in good yields.