A thiazine-S-oxide, Staudinger/aza-Wittig based synthesis of benzodiazepines and benzothiadiazepines

被引:26
|
作者
Anwar, B
Grimsey, P
Hemming, K [1 ]
Krajniewski, M
Loukou, C
机构
[1] Univ Hertfordshire, Dept Phys Sci, Hatfield AL10 9AB, Herts, England
[2] Univ Bath, Sch Chem, Bath BA2 7AY, Avon, England
基金
英国工程与自然科学研究理事会;
关键词
benzodiazepines; benzothiadiazepines; aza-Wittig reaction; thiazine-S-oxides;
D O I
10.1016/S0040-4039(00)01797-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new approach to the synthesis of imine containing 1,2,5-benzothiadiazepine-1,1-dioxides and 1,4-benzodiazepin-5-ones using iminophosphoranyl thiazine-S-oxides as precursors is reported. Key steps include a Staudinger reaction, an aza-Wittig reaction and the conversion of a thiazine-S-oxide into an amino ketone via a [2,3] sigmatropic rearrangement. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:10107 / 10110
页数:4
相关论文
共 50 条
  • [31] New efficient synthesis of polysubstituted 3,4-dihydroquinazolines and 4H-3,1-benzothiazines through a Passerini/Staudinger/aza-Wittig/addition/nucleophilic substitution sequence
    Zhao, Long
    Yang, Mao-Lin
    Liu, Min
    Ding, Ming-Wu
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2022, 18 : 286 - 292
  • [32] New and Efficient Synthesis of 2,3,4-Trisubstituted 2H-Pyrrolo[3,4-c]quinolines via a MCR/Staudinger/Aza-Wittig Sequence
    Qu, Feng
    Hu, Ruo-Fei
    Gao, Le
    Wu, Jing
    Cheng, Xiao-Hong
    Wang, Song
    He, Ping
    SYNTHESIS-STUTTGART, 2015, 47 (23): : 3701 - 3710
  • [33] Synthesis of substituted 2-amino-5,6-dihydropyrimidin-4-ones using an aza-Wittig reaction
    Kochubey V.S.
    Blochin Ya.S.
    Rodin O.G.
    Perevalov V.P.
    Chem. Heterocycl. Compd., 2006, 7 (897-900): : 897 - 900
  • [34] Aza-Wittig reaction of (β-diazo-α,α-difluoroethyl)phosphonates with aldehydes for the synthesis of difluoromethylphosphonate-containing arylidene hydrazones
    Wang, Qian
    Pajkert, Romana
    Mei, Haibo
    Roeschenthaler, Gerd-Volker
    Han, Jianlin
    JOURNAL OF FLUORINE CHEMISTRY, 2024, 273
  • [35] A convenient E-diastereoselective synthesis of NH-isatin N ?-arylimines via the aza-Wittig reaction
    Filatov, Vadim E.
    Iuzabchuk, Dmitrii A.
    Tarasevich, Boris N.
    Zyk, Nikolai ., V
    Beloglazkina, Elena K.
    MENDELEEV COMMUNICATIONS, 2022, 32 (05) : 634 - 636
  • [36] One-pot synthesis of polysubstituted quinazolin-4(3H)-ones via sequential oxidative Ugi/Staudinger/aza-Wittig reactions starting from tertiary amines
    Sun, Mei
    Yu, Yan-Ling
    Zhao, Long
    Ding, Ming-Wu
    TETRAHEDRON, 2021, 96
  • [37] A SYNTHESIS OF 1,3,4-OXADIAZOLES VIA THE AZA-WITTIG REACTION OF N-ACYLAMINO IMINOTRIPHENYLPHOSPHORANES
    FROYEN, P
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1991, 57 (1-2): : 11 - 15
  • [38] An Efficient Protocol for the Synthesis of Pyrazolo[1,5-c]quinazolines by a Staudinger-Aza-Wittig-Dehydroaromatization Sequence
    Xu, Mingxian
    Chen, An
    Ren, Zhilin
    Qiu, Jiying
    Zu, Mingming
    Zhang, Yi
    Wang, Jiayi
    He, Ping
    SYNLETT, 2021, 32 (18) : 1874 - 1878
  • [39] Facile Synthesis of 5-Carboxamide-oxazolines via a Passerini 3CC-Staudinger-aza-Wittig Sequence
    Wu, Jing
    Liu, Jian-Chao
    Wang, Long
    Ding, Ming-Wu
    SYNLETT, 2011, (19) : 2880 - 2882
  • [40] Novel synthesis of 3-substituted 2-thiohydantoins via Aza-Wittig reaction on poly(ethylene glycol)
    Xiang, Fengying
    Zhang, Shoubo
    Lu, Cuifen
    Chen, Zuxing
    Yang, Guichun
    SYNTHETIC COMMUNICATIONS, 2008, 38 (06) : 953 - 960