Staudinger and retro-Staudinger reactions. The dichloro-β-lactam moiety as a useful handle for the synthesis of 4-aryl-2H-1,3-benzothiazine 1,1-dioxides

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Abstract

The dichloro-β-lactam ring, obtained via Staudinger reaction of 4-aryl-2H-1,3-benzothiazines, proved to be a useful protecting strategy for the synthesis of 4-aryl-2H-1,3-benzothiazine 1,1-dioxides. After oxidation of the 1,1-dichloroazeto[2,1-c][1,3]-benzothiazin-2-ones, the thiazine ring could be recovered selectively and in good yield by treatment with base. Thus, novel 4-aryl-2H-1,3-benzothiazine 1,1-dioxides were obtained efficiently.

Original languageEnglish
Pages (from-to)3205-3207
Number of pages3
JournalTetrahedron Letters
Volume51
Issue number24
DOIs
Publication statusPublished - jún. 16 2010

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Thiazines
Lactams
Oxidation

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

@article{fffb901bbc5547e6898d428a8b1a0522,
title = "Staudinger and retro-Staudinger reactions. The dichloro-β-lactam moiety as a useful handle for the synthesis of 4-aryl-2H-1,3-benzothiazine 1,1-dioxides",
abstract = "The dichloro-β-lactam ring, obtained via Staudinger reaction of 4-aryl-2H-1,3-benzothiazines, proved to be a useful protecting strategy for the synthesis of 4-aryl-2H-1,3-benzothiazine 1,1-dioxides. After oxidation of the 1,1-dichloroazeto[2,1-c][1,3]-benzothiazin-2-ones, the thiazine ring could be recovered selectively and in good yield by treatment with base. Thus, novel 4-aryl-2H-1,3-benzothiazine 1,1-dioxides were obtained efficiently.",
keywords = "1,3-Benzothiazine, Dichloro-β-lactam, Oxidation, Staudinger reaction",
author = "L. Fodor and P. Csom{\'o}s and A. Cs{\'a}mpai and P. Soh{\'a}r",
year = "2010",
month = "6",
day = "16",
doi = "10.1016/j.tetlet.2010.04.051",
language = "English",
volume = "51",
pages = "3205--3207",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Elsevier Limited",
number = "24",

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TY - JOUR

T1 - Staudinger and retro-Staudinger reactions. The dichloro-β-lactam moiety as a useful handle for the synthesis of 4-aryl-2H-1,3-benzothiazine 1,1-dioxides

AU - Fodor, L.

AU - Csomós, P.

AU - Csámpai, A.

AU - Sohár, P.

PY - 2010/6/16

Y1 - 2010/6/16

N2 - The dichloro-β-lactam ring, obtained via Staudinger reaction of 4-aryl-2H-1,3-benzothiazines, proved to be a useful protecting strategy for the synthesis of 4-aryl-2H-1,3-benzothiazine 1,1-dioxides. After oxidation of the 1,1-dichloroazeto[2,1-c][1,3]-benzothiazin-2-ones, the thiazine ring could be recovered selectively and in good yield by treatment with base. Thus, novel 4-aryl-2H-1,3-benzothiazine 1,1-dioxides were obtained efficiently.

AB - The dichloro-β-lactam ring, obtained via Staudinger reaction of 4-aryl-2H-1,3-benzothiazines, proved to be a useful protecting strategy for the synthesis of 4-aryl-2H-1,3-benzothiazine 1,1-dioxides. After oxidation of the 1,1-dichloroazeto[2,1-c][1,3]-benzothiazin-2-ones, the thiazine ring could be recovered selectively and in good yield by treatment with base. Thus, novel 4-aryl-2H-1,3-benzothiazine 1,1-dioxides were obtained efficiently.

KW - 1,3-Benzothiazine

KW - Dichloro-β-lactam

KW - Oxidation

KW - Staudinger reaction

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U2 - 10.1016/j.tetlet.2010.04.051

DO - 10.1016/j.tetlet.2010.04.051

M3 - Article

VL - 51

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EP - 3207

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 24

ER -