SYNTHESIS OF 6-ALKOXY-3-ARYL-6-TRIMETHYLSILYLOXY-5,6-DIHYDRO-4H-1,2-OXAZINES AND THEIR ACID-CATALYZED HYDROLYSIS LEADING TO 3-ARYL-5,6-DIHYDRO-4H-1,2-OXAZIN-6-ONES AND OR 4-ARYL-4-(HYDROXYIMINO)BUTYRIC ACID-ESTERS

被引：6
|
作者：
TANIMOTO, S
MATSUMOTO, H
HOJO, M
TOSHIMITSU, A
机构：
来源：
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1991年 / 12期
关键词：
D O I：
10.1039/p19910003153
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The cycloaddition of alpha-nitrosostyrene and its ring-substituted derivatives, which are generated by the reaction of alpha-chloroacetophenone oxime and its ring-substituted derivatives with K2CO3 in tetrahydrofuran, with ketene trimethylsilyl acetals proceeds to afford 6-alkoxy-3-aryl-6-trimethylsilyloxy-5,6-dihydro-4H-1,2-oxazines. These oxazines are susceptible to hydrochloric acid-catalysed hydrolysis affording 3-aryl-5,6-dihydro-4H-1,2-oxazin-6-one and/or 4-aryl-4-(hydroxyimino)butyric acid esters.
引用
收藏
页码：3153 / 3157
页数：5
相关论文
共 50 条
  • [31] Synthesis of new series of 5,6-dihydro-4H-1,2-oxazines via hetero Diels-Alder reaction and evaluation of antimicrobial activity
    Manjula, M. K.
    Rai, K. M. L.
    Gaonkar, S. L.
    Raveesha, K. A.
    Satish, S.
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2009, 44 (01) : 280 - 288
  • [32] A novel photochemical synthesis of 5,6-dihydro-4H-1,2-oxazines by DCA-sensitized irradiation of gamma,delta-unsaturated oximes
    Armesto, D
    Austin, MA
    Griffiths, OJ
    Horspool, WM
    Carpintero, M
    CHEMICAL COMMUNICATIONS, 1996, (24) : 2715 - 2716
  • [33] Microwave-Assisted Synthesis of 2-Aryl-2-oxazolines, 5,6-Dihydro-4H-1,3-oxazines, and 4,5,6,7-Tetrahydro-1,3-oxazepines
    Mollo, Maria C.
    Orelli, Liliana R.
    ORGANIC LETTERS, 2016, 18 (23) : 6116 - 6119
  • [34] SYNTHESIS OF 2-DIPHENYLMETHYLENE-3-PARA-TOLYL-6-ARYL-2,3-DIHYDRO-4H-1,3-OXAZIN-4-ONES
    ANDREICHIKOV, YS
    SHUROV, SN
    IGIDOV, NM
    ZHURNAL ORGANICHESKOI KHIMII, 1986, 22 (01): : 230 - 230
  • [35] One-pot cyclizations of dilithiated oximes and hydrazones with epibromohydrin.: Efficient synthesis of 6-hydroxymethyl-5,6-dihydro-4H-1,2-oxazines and oxazolo[3,4-b]pyridazin-7-ones
    Dang, TT
    Albrecht, U
    Gerwien, K
    Siebert, M
    Langer, P
    JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (06): : 2293 - 2301
  • [36] REDUCTIVE TRANSFORMATIONS OF 5,6-DIHYDRO-4H-1,2-OXAZINES - SYNTHESIS OF 4-HYDROXY KETOXIMES, N-HYDROXYPYRROLIDINE DERIVATIVES, AND OTHER NITROGEN-CONTAINING COMPOUNDS
    HIPPELI, C
    REISSIG, HU
    LIEBIGS ANNALEN DER CHEMIE, 1990, (05): : 475 - 481
  • [37] Antioxidant and DNA damage inhibition activities of 4-Aryl-N-(4-aryl-thiazol-2-yl)-5,6-dihydro-4H-1,3,4-oxadiazine-2-carboxamides
    Shubakara, K.
    Umesha, K. B.
    Srikantamurthy, N.
    Chethan, J.
    JOURNAL OF CHEMICAL SCIENCES, 2014, 126 (06) : 1913 - 1921
  • [38] H3PW12O40: An Efficient and Recyclable Heterogeneous Catalyst for the Selective Synthesis of 2-Aryl-5,6-dihydro-4H-1,3-oxazines and 2-Aryl-1,4,5,6-tetrahydropyrimidines
    Mohammadpoor-Baltork, Iraj
    Moghadam, Majid
    Tangestaninejad, Shahram
    Mirkhani, Valiollah
    Eskandari, Zohre
    ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 2010, 65 (04): : 461 - 469
  • [39] Preparation of cyclic and bicyclic β-amino acids derivatives from methyl 6-ethoxy-5,6-dihydro-4H-1,2-oxazine-4-carboxylate
    Tishkov, AA
    Reissig, HU
    Ioffe, SL
    SYNLETT, 2002, (06) : 863 - 866
  • [40] SYNTHESIS OF 6H-6-HYDROXY-5,6-DIPHENYL-3-ARYL-1,2-OXAZINES - PREPARATION OF 2-AZAPYRYLIUM AND 1,2-OXAZINIUM IONS
    SHELYAPIN, OP
    SAMARTSE.IV
    PAVLOVA, LA
    ZHURNAL ORGANICHESKOI KHIMII, 1974, 10 (07): : 1513 - 1518
12345