Sequential Hydroperoxylation and Amberlyst-15 Catalyzed Hock-type Rearrangement of Spiroepoxy/Spiroaziridine Oxindoles for the Synthesis of 2-Hydroxybenzo[b][1,4]oxazin-3(4H)-ones

被引：0
作者：
Abu Saleh, S. K. [1 ]
Mondal, Ananda Shankar [1 ]
Senapati, Swarup [1 ]
Hajra, Saumen [1 ]
机构：
[1] Sanjay Gandhi Postgrad Inst Med Sci Campus, Ctr Biomed Res, Raebareli Rd, Lucknow 226014, India
来源：
ASIAN JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 13卷 / 02期
关键词：
Aziridines; Epoxides; Hydroperoxides; Rearrangement; Oxindoles; ORGANIC PEROXIDES; DEFENSE CHEMICALS; 2-HYDROXY-1,4-BENZOXAZIN-3-ONE; HYDROGEN;
D O I：
10.1002/ajoc.202300581
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A sequential one-pot reaction of spiro-aziridine/epoxy oxindoles with aq. H2O2 followed by with amberlyst-15 catalyst directly gave 2-hydroxy-2-substituted-2H-benzo[b][1,4]oxazin-3(4H)-ones and subsequent reaction with either aldehydes/ketones or carbonyldiimidazole (CDI) gave spiro[benzo[b][1,4]oxazine-2,4 '-[1,3]dioxolan]-3(4H)-ones or spiro[benzo[b][1,4]oxazine-2,4 '-[1,3]dioxolane]-2 ',3(4H)-diones, respectively.
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页数：6
相关论文
共 37 条
  • [1] Casteel DA, 1999, NAT PROD REP, V16, P55
  • [2] Sn-Catalyzed Criegee-Type Rearrangement of Peroxyoxindoles Enabled by Catalytic Dual Activation of Esters and Peroxides
    Chaudhari, Moreshwar B.
    Jayan, Krishna
    Gnanaprakasam, Boopathy
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (05) : 3374 - 3382
  • [3] The Rearrangement of Peroxides for the Construction of Fluorophoric 1,4-Benzoxazin-3-one Derivatives
    Chaudhari, Moreshwar B.
    Chaudhary, Atul
    Kumar, Vishnupriya
    Gnanaprakasam, Boopathy
    [J]. ORGANIC LETTERS, 2019, 21 (06) : 1617 - 1621
  • [4] CRIEGEE R, 1948, LIEBIGS ANN CHEM, V560, P127
  • [5] Dakin H. D., 1909, Am. Chem. J., V42, P477
  • [6] Bioactive peroxides as potential therapeutic agents
    Dembitsky, Valery M.
    [J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2008, 43 (02) : 223 - 251
  • [7] Strength of solid acids and acids in solution. Enhancement of acidity of centers on solid surfaces by anion stabilizing solvents and its consequence for catalysis
    Farcasiu, D
    Ghenciu, A
    Marino, G
    Rose, KD
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (49) : 11826 - 11831
  • [8] Aqueous tert-Butyl Hydroperoxide Mediated Regioselective Ring-Opening Reactions of Spiro-aziridine-epoxy Oxindoles: Synthesis of 3-Peroxy-3-substituted Oxindoles and Their Acid-Mediated Rearrangement
    Hajra, Saumen
    Hazra, Atanu
    Abu Saleh, S. K.
    Mondal, Ananda Shankar
    [J]. ORGANIC LETTERS, 2019, 21 (24) : 10154 - 10158
  • [9] Domino Corey-Chaykovsky Reaction for One-Pot Access to Spirocyclopropyl Oxindoles
    Hajra, Saumen
    Roy, Sayan
    Abu Saleh, S. K.
    [J]. ORGANIC LETTERS, 2018, 20 (15) : 4540 - 4544
  • [10] Hassall C.H., 2011, BAEYER VILLIGER OXID
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