Preparation and ring transformation of isomeric β-lactam derivatives of bicyclic 1,3-thiazines

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7 Citations (Scopus)

Abstract

Ketene-imine cycloaddition reactions between cis- and trans-2-aryl-4a,5,6, 7,8,8a-hexahydro-4H-3,1-benzothazines and chloroacetyl chloride in the presence of base were investigated. Because of the diastereotopic CN faces of cyclohexane-condensed thiazines, both of the possible Staudinger addition product monochloro-β-lactam stereoisomers were obtained for both the cis and the trans compounds. The novel azetidin-2-ones were transformed into the corresponding 3-ethoxycarbonyl-2-aryl-1,5,5a,6,7,8,9,9a-octahydro-4,1- benzothiazepines with sodium ethoxide in a one-step procedure. Structural and stereochemical analyses of the synthesized compounds were carried out by means of IR and NMR spectroscopy.

Original languageEnglish
Pages (from-to)410-417
Number of pages8
JournalTetrahedron
Volume69
Issue number1
DOIs
Publication statusPublished - jan. 7 2013

Fingerprint

Thiazines
Lactams
Stereoisomerism
Imines
Cycloaddition
Cycloaddition Reaction
Nuclear magnetic resonance spectroscopy
Infrared spectroscopy
Magnetic Resonance Spectroscopy
Derivatives
chloroacetyl chloride
Cyclohexane
sodium ethoxide
ketene

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

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title = "Preparation and ring transformation of isomeric β-lactam derivatives of bicyclic 1,3-thiazines",
abstract = "Ketene-imine cycloaddition reactions between cis- and trans-2-aryl-4a,5,6, 7,8,8a-hexahydro-4H-3,1-benzothazines and chloroacetyl chloride in the presence of base were investigated. Because of the diastereotopic CN faces of cyclohexane-condensed thiazines, both of the possible Staudinger addition product monochloro-β-lactam stereoisomers were obtained for both the cis and the trans compounds. The novel azetidin-2-ones were transformed into the corresponding 3-ethoxycarbonyl-2-aryl-1,5,5a,6,7,8,9,9a-octahydro-4,1- benzothiazepines with sodium ethoxide in a one-step procedure. Structural and stereochemical analyses of the synthesized compounds were carried out by means of IR and NMR spectroscopy.",
keywords = "β-Lactam isomers, Enamine, Ketene-imine cycloaddition, Ring transformation, Stereostructure and conformation determination by NMR including NOE, Thiazepine, Thiazine",
author = "L. Fodor and P. Csom{\'o}s and F. F{\"u}l{\"o}p and A. Cs{\'a}mpai and P. Soh{\'a}r",
year = "2013",
month = "1",
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doi = "10.1016/j.tet.2012.09.102",
language = "English",
volume = "69",
pages = "410--417",
journal = "Tetrahedron",
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T1 - Preparation and ring transformation of isomeric β-lactam derivatives of bicyclic 1,3-thiazines

AU - Fodor, L.

AU - Csomós, P.

AU - Fülöp, F.

AU - Csámpai, A.

AU - Sohár, P.

PY - 2013/1/7

Y1 - 2013/1/7

N2 - Ketene-imine cycloaddition reactions between cis- and trans-2-aryl-4a,5,6, 7,8,8a-hexahydro-4H-3,1-benzothazines and chloroacetyl chloride in the presence of base were investigated. Because of the diastereotopic CN faces of cyclohexane-condensed thiazines, both of the possible Staudinger addition product monochloro-β-lactam stereoisomers were obtained for both the cis and the trans compounds. The novel azetidin-2-ones were transformed into the corresponding 3-ethoxycarbonyl-2-aryl-1,5,5a,6,7,8,9,9a-octahydro-4,1- benzothiazepines with sodium ethoxide in a one-step procedure. Structural and stereochemical analyses of the synthesized compounds were carried out by means of IR and NMR spectroscopy.

AB - Ketene-imine cycloaddition reactions between cis- and trans-2-aryl-4a,5,6, 7,8,8a-hexahydro-4H-3,1-benzothazines and chloroacetyl chloride in the presence of base were investigated. Because of the diastereotopic CN faces of cyclohexane-condensed thiazines, both of the possible Staudinger addition product monochloro-β-lactam stereoisomers were obtained for both the cis and the trans compounds. The novel azetidin-2-ones were transformed into the corresponding 3-ethoxycarbonyl-2-aryl-1,5,5a,6,7,8,9,9a-octahydro-4,1- benzothiazepines with sodium ethoxide in a one-step procedure. Structural and stereochemical analyses of the synthesized compounds were carried out by means of IR and NMR spectroscopy.

KW - β-Lactam isomers

KW - Enamine

KW - Ketene-imine cycloaddition

KW - Ring transformation

KW - Stereostructure and conformation determination by NMR including NOE

KW - Thiazepine

KW - Thiazine

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U2 - 10.1016/j.tet.2012.09.102

DO - 10.1016/j.tet.2012.09.102

M3 - Article

AN - SCOPUS:84870063644

VL - 69

SP - 410

EP - 417

JO - Tetrahedron

JF - Tetrahedron

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