TBHP/KI-Promoted Oxidative Cyclization of α-Aminoketones for One-Pot Synthesis of Substituted 2-Acyloxazoles

Abstract

A metal-free and facile synthesis of substituted 2-acyloxazole derivatives from α-aminoketones was developed via a TBHP/KI-promoted oxidative cyclization. This procedure proceeded smoothly under mild conditions and a broad scope of 2-acyloxazoles were obtained in moderate to good yields.

Key words

metal-free - TBHP/KI - 2-acyloxazole - oxidative cyclization

Publikationsverlauf

Eingereicht: 14. Oktober 2022

Angenommen nach Revision: 12. Dezember 2022

Accepted Manuscript online:
12. Dezember 2022

Artikel online veröffentlicht:
05. Januar 2023

• References

• 1 Boger DL, Miyauchi H, Du W, Hardouin C, Fecik RA, Cheng H, Hwang I, Hedrick MP, Leung D, Acevedo O, Guimarães CR. W, Jorgensen WL. J. Med. Chem. 2005; 48: 1849
• 2a Zhang RQ, Mo HL, Ma YY, Zhao DG, Zhang K, Zhang TW, Chen XC, Zheng X. Bioorg. Med. Chem. Lett. 2021; 40: 127968
• 2b Liu MM, Liang YR, Zhu ZZ, Wang J, Cheng XX, Cheng JY, Xu BP, Li R, Liu XH. J. Med. Chem. 2019; 62: 9299
• 2c Robles AJ, Mccowen S, Cai SX, Glassman M, Ruiz F, Cichewicz RH, McHardy SF, Mooberry SL. J. Med. Chem. 2019; 60: 9275
• 3 Rafael DR, Dambrós BP, Moraes DM. H, Grand L, Jacolot M, Popowyz F, Steindel M, Schenkel EP, Bernardes LS. C. Bioorg. Chem. 2022; 119: 105492
• 4 Harris PA, Berger SB, Jeong JU, Nagilla R, Bandyopadhyay D, Campobasso N, Capriotti CA, Cox JA, Dare L, Dong XY, Eidam PM, Finger JN, Hoffman SJ, Kang J, Kasparcova V, King BW, Lehr R, Lan YF, Leister LK, Lich JD, MacDonald TT, Miller NA, Ouellette MT, Pao CS, Rahman A, Reilly MA, Rendina AR, Rivera EJ, Schaeffer MC, Sehon CA, Singhaus RR, Sun HH, Swift BA, Totoritis RD, Vossenkämper A, Ward P, Wisnoski DD, Zhang DH, Marquis RW, Gough PJ, Bertin J. J. Med. Chem. 2017; 60: 1247
• 5 Jiang HF, Huang HW, Cao H, Qi CR. Org. Lett. 2010; 12: 5561
• 6 Yang K, Zhang C, Wang P, Kadi AA, Fun HK, Zhang Y, Lu HJ. Eur. J. Org. Chem. 2014; 34: 7586
• 7 Ogiwara Y, Iino Y, Sakai N. Chem. Eur. J. 2019; 25: 6513
• 8a Xue WJ, Zhang W, Zheng KL, Dai Y, Guo YQ, Li HZ, Gao FF, Wu AX. Asian J. Org. Chem. 2013; 2: 638
• 8b Cheng Y, Xiang JC, Wang ZX, Ma JT, Wang M, Tang BC, Wu YD, Zhu YP, Wu AX. Adv. Synth. Catal. 2018; 360: 550
• 9 Zhang SS, Zhao QL, Zhao YF, Yu WQ, Chang JB. Adv. Synth. Catal. 2020; 362: 1993
• 10 Zhu YP, Zhou Y, Li WJ, Liu FR, Wang WC, Hao KY, Chao BY, Shi TR, Wu AX, Sun YY. J. Org. Chem. 2022; 87: 12460
• 11a Liu CK, Yang Z, Zeng Y, Fang Z, Guo K. Asian J. Org. Chem. 2017; 6: 1104
• 11b Wan CF, Gao LF, Wang Q, Zhang JT, Wang ZY. Org. Lett. 2010; 12: 3902
• 11c Vadagaonkar KS, Kalmode HP, Murugan K, Chaskar AC. RSC Adv. 2015;  5: 5580
• 12a Long BY, Tian BH, Qiang T, Hu XN, Han L, Wang ZF, Wang CY, Wu Y, Yu Y, Gan ZJ. Tetrahedron 2021; 96: 132382
• 12b Gan ZJ, Tian BH, Yuan JY, Ran DZ, Zhang L, Dong G, Pan T, Zeng YX, Yu Y. Tetrahedron Lett. 2020; 61: 152195
• 12c Han L, Gan LL, Hu XN, Li W, Zhu DL, Zheng JC, Wu Y, Yu Y, Gan ZJ. Synth. Commun. 2022; 52: 1050
• 13 Zhou BC, Guo SY, Fang Z, Yang Z, Liu CK, He W, Zhu N, Li X, Guo K. Synthesis 2019; 51: 3511
• 14 CCDC 2220726 (2a) contains the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/structures
• 15 Cao ZZ, Lv HF, Liu YF, Nie ZW, Liu HP, Yang TL, Luo WP, Liu Q, Guo CC. Adv. Synth. Catal. 2019; 361: 1632
• 16a Zhang J, Zhao X, Liu P, Sun PP. J. Org. Chem. 2019; 84: 12596
• 16b Duan XY, Kong XL, Zhao XY, Yang K, Zhou HY, Zhou DJ, Zhang YP, Liu JW, Ma JY, Liu N, Wang ZC. Tetrahedron Lett. 2016; 57: 1446
• 16c Ishihara M, Togo H. Synlett 2006; 227
• 17 Pogaku N, Krishna PR, Prapurna YL. Synth. Commun. 2018; 48: 1986