Synthesis of the substituted 7H-pyrano[2,3-d]isoxazol-7-ones from allomaltol-containing oximes

被引:2
|
作者
Milyutin, Constantine V. [1 ]
Komogortsev, Andrey N. [1 ]
Melekhina, Valeriya G. [1 ]
Lichitsky, Boris V. [1 ]
机构
[1] Russian Acad Sci, ND Zelinsky Inst Organ Chem, Moscow, Russia
关键词
7H-pyrano[2,3-d]isoxazol-7-one; diketone monoxime; allomaltol; two-stage process; hydrazone; GENERATED NITRILE OXIDES; EFFICIENT SYNTHESIS; 3+2 CYCLOADDITION; FACILE SYNTHESIS; BENZISOXAZOLES; ACIDS; 1,2-BENZISOXAZOLES; DERIVATIVES; INHIBITORS;
D O I
10.1080/00397911.2023.2272208
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Convenient approach for the synthesis of previously unknown 7H-pyrano[2,3-d]isoxazol-7-one core was elaborated. The presented method is based on two stage process including preparation of diketone monoximes and their subsequent intramolecular dehydration. It was shown that among various dehydrating agents the best results were achieved using system TsCl/Et3N. The advantages of the considered procedure are easily available starting compounds, simple experimental procedure and isolation of the final products, avoiding column chromatography.
引用
收藏
页码:2108 / 2116
页数:9
相关论文
共 50 条
  • [31] SYNTHESIS OF 2-SUBSTITUTED 2,6-DIHYDRO-3-HYDROXY-7H-PYRAZOLO[4,3-D]PYRIMIDIN-7-ONES
    OCHI, H
    MIYASAKA, T
    CHEMICAL & PHARMACEUTICAL BULLETIN, 1983, 31 (04) : 1228 - 1234
  • [32] Single-step synthesis of substituted 7-aminopyrano[2,3-d]pyrimidines
    A. A. Shestopalov
    L. A. Rodinovskaya
    A. M. Shestopalov
    V. P. Litvinov
    Russian Chemical Bulletin, 2004, 53 : 2342 - 2344
  • [33] Derivatives of condensed thieno[2,3-d]-pyrimidines. 20. Synthesis of 2-substituted 5,6-dihydro-8H-pyrano[4′,3′:4,5]thieno[2,3-d] pyrimidin-4(3H)-ones and 5,6,7,8-tetrahydrobenzo-[b]thieno[2,3-d]pyrimidin-4- ones
    Mkrtchyan A.P.
    Noravyan A.S.
    Chem. Heterocycl. Compd., 2006, 3 (392-395): : 392 - 395
  • [35] Derivatives of the condensed thieno[2,3-d]pyrimidines.: 20.: Synthesis of 2-substituted 5,6-dihydro-8H-pyrano[4′,3′:4,5]thieno[2,3-d]pyrimidin-4(3H)-ones and 5,6,7,8-tetrahydrobenzo[b]thieno[2,3-d]pyrimidin-4(3H)-ones
    Mkrtchyan, AP
    Noravyan, AS
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 2006, (03): : 441 - 444
  • [36] 7-deazainosine derivatives:: Synthesis and characterization of 7- and 7,8-substituted pyrrolo [2,3-d]pyrimidine ribonucleosides
    Ciliberti, Nunzia
    Durini, Elisa
    Manfredini, Stefano
    Vertuani, Silvia
    NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 2008, 27 (05): : 525 - 533
  • [37] Pyrrolo[2,3-d]pyrimidine nucleosides:: Synthesis and antitumor activity of 7-substituted 7-deaza-2′-deoxyadenosines
    Seela, F
    Zulauf, M
    Chen, SF
    NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 2000, 19 (1-2): : 237 - 251
  • [38] PHOSPHORUS PENTOXIDE IN ORGANIC-SYNTHESIS .21. SYNTHESIS OF 7H-PYRROLO[2,3-D]PYRIMIDIN-4(3H)-ONES AND N-ARYL-7H-PYRROLO[2,3-D]PYRIMIDIN-4-AMINES
    JORGENSEN, A
    ELBAYOUKI, KAM
    PEDERSEN, EB
    CHEMICA SCRIPTA, 1985, 25 (03): : 222 - 226
  • [39] Design, synthesis and biological evaluation of pyrido[2,3-d]pyrimidin-7-(8H)-ones as HCV inhibitors
    Camarasa, Marta
    Puig de la Bellacasa, Raimon
    Gonzalez, Alex L.
    Ondono, Raul
    Estrada, Roger
    Franco, Sandra
    Badia, Roger
    Este, Jose
    Angel Martinez, Miguel
    Teixido, Jordi
    Clotet, Bonaventura
    Borrell, Jose I.
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2016, 115 : 463 - 483
  • [40] Synthesis of new 4-amino-substituted 7-iminopyrido[2,3-d]pyrimidines
    Zinchenko, Anna N.
    Muzychka, Lyubov V.
    Biletskii, Igor I.
    Smolii, Oleg B.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2017, 53 (05) : 589 - 596