and synthesis of the derivatives of serines as a antibiotics [13] synthesis of N-hydroxy-N-amino acids [14] and as starting material in the synthesis of the neurotrophic factor Lactacystin [15,16]. Moreover, various oxazolines with biological activity have been isolated from marine organisms [17,18].For many years, several synthetic methods have been described for the synthesis of oxazolines [19][20][21][22]. On the other hand, Aziridines are also well known as useful reagents for the synthesis of many categories of nitrogencontaining compounds, in particular N-heterocycles compounds such as oxazolines, thiazolidinones, thiazolidine thiones, and imidazolidinones [23].Among the synthetic applications of these compounds, the rearrangement of N-activated aziridines has become the object of attention only very recently [24]. Acyl aziridines could rearrange to oxazolines through a ring expansion reaction [25][26][27][28][29]. The ring expansion of N-acyl aziridines to oxazolines can be promoted by thermal, acidic, or nucleophilic conditions [30][31][32][33][34][35][36][37][38].However, catalytic examples for the synthesis of oxazolines are rare [39]. Here we report synthesis of N-acyl ketoaziridines from the corresponding ketoaziridines with acyl chlorides. Then N-acyl ketoaziridines in the presence of a nucleophilic and Lewis acids afforded oxazolines [40][41][42].Although a few methods have been described for the preparation of N-acyl aziridines none of them described direct synthesis of oxazolines from N-H aziridines with carboxylic acid .In continuation of our recent interest in the reaction of ketoaziridines [48] and success for using Polyoxometalates [49], herein, we report a one-pot regio-and stereo-selective synthesis of trans-4-benzoyloxazolines, catalyzed by the K 5 [PW 11 ZnO 39 ].23H 2 O catalytic system with moderate to good yields under mild conditions. Abstract A new and one-pot synthesis of oxazolines has been accomplished by K 5 [PW 11 ZnO 39 ].23H 2 O-catalyst acylation followed by C-N ring opening/C-O bond formation in NH ketoaziridines. This regio-and stereo-selective reaction presumably proceeds via a domino sequence resulting in the in situ generation of acyl aziridine which undergoes a ring expansion reaction via an initial C-N rupture of aziridine ring followed by ring closure to the oxazolines. The methodology provided novel one-pot procedure for the synthesis of trans-2,5-diaryl-4-aroyloxazolines.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.
customersupport@researchsolutions.com
10624 S. Eastern Ave., Ste. A-614
Henderson, NV 89052, USA
This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.
Copyright © 2024 scite LLC. All rights reserved.
Made with 💙 for researchers
Part of the Research Solutions Family.