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Synthesis 2023; 55(09): 1419-1426
DOI: 10.1055/a-1996-8388
paper

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

Jiecheng Zheng‡
a   Department of Medicinal Chemistry, College of Pharmacy, Chongqing Medical University, Chongqing 400016, P. R. of China
,
Dali Zhu‡
a   Department of Medicinal Chemistry, College of Pharmacy, Chongqing Medical University, Chongqing 400016, P. R. of China
,
Zhangyou Yang
a   Department of Medicinal Chemistry, College of Pharmacy, Chongqing Medical University, Chongqing 400016, P. R. of China
,
Huali Chen
a   Department of Medicinal Chemistry, College of Pharmacy, Chongqing Medical University, Chongqing 400016, P. R. of China
,
Wei Wang
b   Chongqing Fuling Institute for Food and Drug Control, Chongqing 408102, P. R. of China
,
Lin Ling Gan∗
c   Chongqing Engineering Research Center of Pharmaceutical Sciences, School of Pharmacy, Chongqing Medical and Pharmaceutical College, Chongqing 401331, P. R. of China
,
Zongjie Gan  ∗
a   Department of Medicinal Chemistry, College of Pharmacy, Chongqing Medical University, Chongqing 400016, P. R. of China
› Author AffiliationsWe appreciate the finical support from the National Natural Science Foundation of China (No. 21907013).
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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

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-1996-8388.
  • Supporting Information


Publication History

Received: 14 October 2022

Accepted after revision: 12 December 2022

Accepted Manuscript online:
12 December 2022

Article published online:
05 January 2023

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  • 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
    CrossrefPubMed
    • 2a Zhang RQ, Mo HL, Ma YY, Zhao DG, Zhang K, Zhang TW, Chen XC, Zheng X. Bioorg. Med. Chem. Lett. 2021; 40: 127968
      CrossrefPubMed
    • 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
      CrossrefPubMed
    • 2c Robles AJ, Mccowen S, Cai SX, Glassman M, Ruiz F, Cichewicz RH, McHardy SF, Mooberry SL. J. Med. Chem. 2019; 60: 9275
      CrossrefPubMed
  • 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
    CrossrefPubMed
  • 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
    CrossrefPubMed
  • 5 Jiang HF, Huang HW, Cao H, Qi CR. Org. Lett. 2010; 12: 5561
    CrossrefPubMed
  • 6 Yang K, Zhang C, Wang P, Kadi AA, Fun HK, Zhang Y, Lu HJ. Eur. J. Org. Chem. 2014; 34: 7586
    CrossrefPubMed
  • 7 Ogiwara Y, Iino Y, Sakai N. Chem. Eur. J. 2019; 25: 6513
    CrossrefPubMed
    • 8a Xue WJ, Zhang W, Zheng KL, Dai Y, Guo YQ, Li HZ, Gao FF, Wu AX. Asian J. Org. Chem. 2013; 2: 638
      Crossref
    • 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
      Crossref
  • 9 Zhang SS, Zhao QL, Zhao YF, Yu WQ, Chang JB. Adv. Synth. Catal. 2020; 362: 1993
    CrossrefPubMed
  • 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
    CrossrefPubMed
    • 11a Liu CK, Yang Z, Zeng Y, Fang Z, Guo K. Asian J. Org. Chem. 2017; 6: 1104
      Crossref
    • 11b Wan CF, Gao LF, Wang Q, Zhang JT, Wang ZY. Org. Lett. 2010; 12: 3902
      CrossrefPubMed
    • 11c Vadagaonkar KS, Kalmode HP, Murugan K, Chaskar AC. RSC Adv. 2015;  5: 5580
      Crossref
    • 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
      Crossref
    • 12b Gan ZJ, Tian BH, Yuan JY, Ran DZ, Zhang L, Dong G, Pan T, Zeng YX, Yu Y. Tetrahedron Lett. 2020; 61: 152195
      Crossref
    • 12c Han L, Gan LL, Hu XN, Li W, Zhu DL, Zheng JC, Wu Y, Yu Y, Gan ZJ. Synth. Commun. 2022; 52: 1050
      Crossref
  • 13 Zhou BC, Guo SY, Fang Z, Yang Z, Liu CK, He W, Zhu N, Li X, Guo K. Synthesis 2019; 51: 3511
    Article in Thieme ConnectPubMed
  • 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
    CrossrefPubMed
    • 16a Zhang J, Zhao X, Liu P, Sun PP. J. Org. Chem. 2019; 84: 12596
      CrossrefPubMed
    • 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
      Crossref
    • 16c Ishihara M, Togo H. Synlett 2006; 227
  • 17 Pogaku N, Krishna PR, Prapurna YL. Synth. Commun. 2018; 48: 1986
    Crossref