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
来源：
TETRAHEDRON LETTERS | 2000年 / 41卷 / 51期
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] Synthesis of γ-Azido-β-ureido Ketones and Their Transformation into Functionalized Pyrrolines and Pyrroles via Staudinger/aza-Wittig Reaction
    Fesenko, Anastasia A.
    Shutalev, Anatoly D.
    JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (03): : 1190 - 1207
  • [32] Biomimetic Synthesis of Urukthapelstatin A by Aza-Wittig Ring Contraction
    Schwenk, Sebastian
    Ronco, Cyril
    Oberheide, Ansgar
    Arndt, Hans-Dieter
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 2016 (28) : 4795 - 4799
  • [33] Recent Advances in the Synthesis of Heterocycles by the Aza-Wittig Reaction
    Pedrood, Keyvan
    Montazer, Mohammad Nazari
    Larijani, Bagher
    Mahdavi, Mohammad
    SYNTHESIS-STUTTGART, 2021, 53 (14): : 2342 - 2366
  • [34] Redox-Neutral Imination of Alcohol with Azide: A Sustainable Alternative to the Staudinger/Aza-Wittig Reaction
    Li, Huaifeng
    Lupp, Daniel
    Das, Pradip K.
    Yang, Li
    Goncalves, Theo P.
    Huang, Mei-Hui
    El Hajoui, Marwa
    Liang, Lan-Chang
    Huang, Kuo-Wei
    ACS CATALYSIS, 2021, 11 (07) : 4071 - 4076
  • [35] Synthesis of Differentially Substituted 2-Aminoimidazolidines via a Microwave-Assisted Tandem Staudinger/Aza-Wittig Cyclization
    Kumar, Rakesh
    Ermolat'ev, Denis S.
    Van der Eycken, Erik V.
    JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (11): : 5737 - 5743
  • [36] Domino Staudinger/aza-Wittig/Mannich Reaction: An Approach to Diversity of Di- and Tetrahydropyrrole Scaffolds
    Pavlova, Anna S.
    Ivanova, Olga A.
    Chagarovskiy, Alexey O.
    Stebunov, Nikolay S.
    Orlov, Nikolay V.
    Shumsky, Alexey N.
    Budynina, Ekaterina M.
    Rybakov, Victor B.
    Trushkov, Igor V.
    CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (50) : 17967 - 17971
  • [37] The Staudinger/aza-Wittig/Grignard reaction as key step for the concise synthesis of 1-C-Alkyl-iminoalditol glycomimetics
    Zoidl, Manuel
    Santana, Andres Gonzalez
    Torvisco, Ana
    Tysoe, Christina
    Siriwardena, Aloysius
    Withers, Stephen G.
    Wrodnigg, Tanja M.
    CARBOHYDRATE RESEARCH, 2016, 429 : 62 - 70
  • [38] Synthesis of cyclopropa[c]indeno[1,2-b]quinolines through a MCR/Staudinger/aza-Wittig sequence
    Nie, Bing-Jie
    Wu, Li-Hui
    Hu, Ruo-Fei
    Sun, Yang
    Wu, Jing
    He, Ping
    Huang, Nian-Yu
    SYNTHETIC COMMUNICATIONS, 2017, 47 (15) : 1368 - 1374
  • [39] Aza-Wittig Polymerization: A Simple Method for the Synthesis of Regioregular Poly(azomethine)s
    Miyake, Junpei
    Chujo, Yoshiki
    MACROMOLECULES, 2008, 41 (24) : 9677 - 9682
  • [40] A convenient synthesis of N-linked diglycose derivatives based on one-pot tandem Staudinger/aza-Wittig/reduction and biological evaluation
    Zhang, Pingzhu
    Li, Yinbo
    Liu, Ming
    Wang, Yanfei
    Li, Cuicui
    Ma, Donglai
    Chen, Hua
    Wang, Kerang
    Li, Xiaoliu
    Zhang, Jinchao
    CARBOHYDRATE RESEARCH, 2013, 372 : 15 - 22
12345