Attempted synthesis of ethyl 3,4-dihydro-2H-1,4-benzoxazine-3-carboxylate and 3-acetate derivatives

被引：20
|
作者：
Mayer, S [1 ]
Arrault, A [1 ]
Guillaumet, G [1 ]
Mérour, JY [1 ]
机构：
[1] Univ Orleans, CNRS, Inst Chim Organ & Analyt, F-45067 Orleans 2, France
来源：
JOURNAL OF HETEROCYCLIC CHEMISTRY | 2001年 / 38卷 / 01期
关键词：
D O I：
10.1002/jhet.5570380133
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Ethyl 3,4-dihydro-2H-1,4-benzoxazine-3-carboxylate derivatives 2 were obtained and isolated in low yields from the condensation of 2-aminophenol and ethyl 2,3-dibromopropanoate. They can be obtained by hydrogenation of ethyl 2H-1,4-benzoxazine-3-carboxylate in satisfactory yield. Using 2-iminophenol did not direct the condensation with ethyl 2,3-dibromopropanoate towards 2 but was fruitfull for the preparation of ethyl 2-(4-benzyl-3,4-dihydro-2H-1,4-benzoxazin-3-yl)acetate from ethyl bromocrotonate.
引用
收藏
页码：221 / 225
页数：5
相关论文
共 50 条
  • [41] SYNTHESIS, CRYSTAL STRUCTURE AND BIOLOGICAL ACTIVITY OF NOVEL SUBSTITUTED N-ACETOXYACETYL-3-METHYL-3,4-DIHYDRO-2H-1,4-BENZOXAZINE
    Ye, Fei
    Wu, Shi-Long
    Gao, Shuang
    Fu, Ying
    INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY, 2015, 24 (04) : 481 - 486
  • [42] Synthesis and antiherpetic activity of novel purine conjugates with 7,8-difluoro-3-methyl-3,4-dihydro-2H-1,4-benzoxazine
    Olga А. Vozdvizhenskaya
    Valeriya L. Andronova
    Georgii А. Galegov
    Galina L. Levit
    Victor P. Krasnov
    Valery N. Charushin
    Chemistry of Heterocyclic Compounds, 2021, 57 : 490 - 497
  • [43] Novel potassium channel activators.: II.: Synthesis and pharmacological evaluation of 3,4-dihydro-2H-1,4-benzoxazine derivatives:: Modification of the aromatic part
    Matsumoto, Y
    Tsuzuki, R
    Matsuhisa, A
    Masuda, N
    Yamagiwa, Y
    Yanagisawa, I
    Shibanuma, T
    Nohira, H
    CHEMICAL & PHARMACEUTICAL BULLETIN, 1999, 47 (07) : 971 - 979
  • [44] Synthesis and antiherpetic activity of novel purine conjugates with 7,8-difluoro-3-methyl-3,4-dihydro-2H-1,4-benzoxazine
    Vozdvizhenskaya, Olga A.
    Andronova, Valeriya L.
    Galegov, Georgii A.
    Levit, Galina L.
    Krasnov, Victor P.
    Charushin, Valery N.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2021, 57 (04) : 490 - 497
  • [45] Methyl 2-(3-oxo-3,4-dihydro-2H-1,4-benzothiazin-4-yl)acetate
    Barryala, Yamna
    Massip, Stephane
    Lazar, Said
    Essassi, El Mokhtar
    Zouihri, Hafid
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2011, 67 : O724 - U2711
  • [46] SYNTHESIS AND REACTIONS OF 3,4-DIHYDRO-2H-1,5-BENZODIOXEPIN-3-ONE
    SCHROTH, W
    WERNER, B
    ZEITSCHRIFT FUR CHEMIE, 1970, 10 (10): : 382 - &
  • [47] Synthesis and Analgesic Activity of bis(3,4-dihydroquinoxalin-2(1H)-one) and bis(3,4-dihydro-2H-1,4-benzoxazin-2-one) Derivatives
    Kulakov, Ivan V.
    Karbainova, Anastasiya A.
    Shulgau, Zarina T.
    Seilkhanov, Tulegen M.
    Gatilov, Yurii V.
    Fisyuk, Alexander S.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2017, 53 (10) : 1094 - 1097
  • [48] Synthesis and Analgesic Activity of bis(3,4-dihydroquinoxalin-2(1H)-one) and bis(3,4-dihydro-2H-1,4-benzoxazin-2-one) Derivatives
    Ivan V. Kulakov
    Anastasiya A. Karbainova
    Zarina T. Shulgau
    Tulegen M. Seilkhanov
    Yurii V. Gatilov
    Alexander S. Fisyuk
    Chemistry of Heterocyclic Compounds, 2017, 53 : 1094 - 1097
  • [49] Acute Toxicity Evaluation of Pyridine Derivatives of 3,4-Dihydroquinoxalin-2-one and 3,4-Dihydro-2H-1,4-benzoxazin-2-one
    Ternovskaya, S. A.
    Vlasenko, V. S.
    Novikov, A. N.
    Dengis, N. A.
    Stalinskaya, A. L.
    Kulakov, I. V.
    RUSSIAN JOURNAL OF BIOORGANIC CHEMISTRY, 2024, 50 (06) : 2627 - 2633
  • [50] (Z)-7-Chloro-3-[(3-chlorophenyl)-methylidene]-4-p-tosyl-3,4-dihydro-2H-1,4-benzoxazine
    Chaudhuri, G
    Helliwell, M
    Kundu, NG
    ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY, 2001, 57 (06): : 740 - 741
12345