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

Balques Anwar; Paul Grimsey; Karl Hemming; Matthew Krajniewski; Christina Loukou

doi:10.1016/S0040-4039(00)01797-4

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

Balques Anwar, Paul Grimsey, Karl Hemming, Matthew Krajniewski, Christina Loukou

Research output: Contribution to journal › Article › peer-review

33 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	10107-10110
Number of pages	4
Journal	Tetrahedron Letters
Volume	41
Issue number	51
DOIs	https://doi.org/10.1016/S0040-4039(00)01797-4
Publication status	Published - 16 Dec 2000
Externally published	Yes

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

abstract = "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.",

keywords = "Aza-Wittig reaction, Benzodiazepines, Benzothiadiazepines, Thiazine-S-oxides",

author = "Balques Anwar and Paul Grimsey and Karl Hemming and Matthew Krajniewski and Christina Loukou",

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T1 - A thiazine-S-oxide, Staudinger/aza-Wittig based synthesis of benzodiazepines and benzothiadiazepines

AU - Anwar, Balques

AU - Grimsey, Paul

AU - Hemming, Karl

AU - Krajniewski, Matthew

AU - Loukou, Christina

PY - 2000/12/16

Y1 - 2000/12/16

N2 - 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.

AB - 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.

KW - Aza-Wittig reaction

KW - Benzodiazepines

KW - Benzothiadiazepines

KW - Thiazine-S-oxides

UR - https://www.scopus.com/pages/publications/0034676683

U2 - 10.1016/S0040-4039(00)01797-4

DO - 10.1016/S0040-4039(00)01797-4

M3 - Article

AN - SCOPUS:0034676683

SN - 0040-4039

VL - 41

SP - 10107

EP - 10110

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 51

ER -

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

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