Transformations of penicillins and cephalosporins

Reactions of chlorosulphonyl isocyanate with penams, cephems, and azetidin-2-ones

Malcolm M Campbell, Robert G Harcus, Kenneth H Nelson

Research output: Contribution to journalArticle

Abstract

Benzyl 6ß-phthalimidopenicillanate reacted with chlorosulphonyl isocyanate to give a thiazolo[3,2-c]pyrimidine derivative by ring expansion of the ß-lactam. The trimethylsilyl derivative of 2,2,2-trichloroethyl 6ß-phenoxyacetamidopenicillanate gave two isomeric thiazolo[3,2-c] pyrimidine derivatives. Methyl 3-methyl-7ß-phenoxyacetamidoceph-3-em carboxylate gave a pyrimido[6,1-b][1,3]thiazine derivative. (3R,4R)-3- Phthalimido-1-(1-benzyloxycarbonyl-2-methylprop-1-enyl)-4-methylthioazetidin-2- one did not give a corresponding ß-lactam ring expansion product, but gave epimeric 4-chloro-products by replacement of the 4-methylthio-group. 4-Acetoxyazetidin-2-one reacted with chlorosulphonyl isocyanate to give an N-allophanoyl derivative.

Original languageEnglish
Pages (from-to)817-822
Number of pages6
JournalJournal of the Chemical Society, Perkin Transactions 1
Issue number8
Publication statusPublished - 1978

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Isocyanates
Cephalosporins
Penicillins
Derivatives
Lactams
Thiazines

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@article{30a54ffdd28346e0bdf097a41c8129a5,
title = "Transformations of penicillins and cephalosporins: Reactions of chlorosulphonyl isocyanate with penams, cephems, and azetidin-2-ones",
abstract = "Benzyl 6{\ss}-phthalimidopenicillanate reacted with chlorosulphonyl isocyanate to give a thiazolo[3,2-c]pyrimidine derivative by ring expansion of the {\ss}-lactam. The trimethylsilyl derivative of 2,2,2-trichloroethyl 6{\ss}-phenoxyacetamidopenicillanate gave two isomeric thiazolo[3,2-c] pyrimidine derivatives. Methyl 3-methyl-7{\ss}-phenoxyacetamidoceph-3-em carboxylate gave a pyrimido[6,1-b][1,3]thiazine derivative. (3R,4R)-3- Phthalimido-1-(1-benzyloxycarbonyl-2-methylprop-1-enyl)-4-methylthioazetidin-2- one did not give a corresponding {\ss}-lactam ring expansion product, but gave epimeric 4-chloro-products by replacement of the 4-methylthio-group. 4-Acetoxyazetidin-2-one reacted with chlorosulphonyl isocyanate to give an N-allophanoyl derivative.",
author = "Campbell, {Malcolm M} and Harcus, {Robert G} and Nelson, {Kenneth H}",
year = "1978",
language = "English",
pages = "817--822",
journal = "Journal of the Chemical Society, Perkin Transactions 1",
issn = "1472-7781",
number = "8",

}

Transformations of penicillins and cephalosporins : Reactions of chlorosulphonyl isocyanate with penams, cephems, and azetidin-2-ones. / Campbell, Malcolm M; Harcus, Robert G; Nelson, Kenneth H.

In: Journal of the Chemical Society, Perkin Transactions 1, No. 8, 1978, p. 817-822.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Transformations of penicillins and cephalosporins

T2 - Reactions of chlorosulphonyl isocyanate with penams, cephems, and azetidin-2-ones

AU - Campbell, Malcolm M

AU - Harcus, Robert G

AU - Nelson, Kenneth H

PY - 1978

Y1 - 1978

N2 - Benzyl 6ß-phthalimidopenicillanate reacted with chlorosulphonyl isocyanate to give a thiazolo[3,2-c]pyrimidine derivative by ring expansion of the ß-lactam. The trimethylsilyl derivative of 2,2,2-trichloroethyl 6ß-phenoxyacetamidopenicillanate gave two isomeric thiazolo[3,2-c] pyrimidine derivatives. Methyl 3-methyl-7ß-phenoxyacetamidoceph-3-em carboxylate gave a pyrimido[6,1-b][1,3]thiazine derivative. (3R,4R)-3- Phthalimido-1-(1-benzyloxycarbonyl-2-methylprop-1-enyl)-4-methylthioazetidin-2- one did not give a corresponding ß-lactam ring expansion product, but gave epimeric 4-chloro-products by replacement of the 4-methylthio-group. 4-Acetoxyazetidin-2-one reacted with chlorosulphonyl isocyanate to give an N-allophanoyl derivative.

AB - Benzyl 6ß-phthalimidopenicillanate reacted with chlorosulphonyl isocyanate to give a thiazolo[3,2-c]pyrimidine derivative by ring expansion of the ß-lactam. The trimethylsilyl derivative of 2,2,2-trichloroethyl 6ß-phenoxyacetamidopenicillanate gave two isomeric thiazolo[3,2-c] pyrimidine derivatives. Methyl 3-methyl-7ß-phenoxyacetamidoceph-3-em carboxylate gave a pyrimido[6,1-b][1,3]thiazine derivative. (3R,4R)-3- Phthalimido-1-(1-benzyloxycarbonyl-2-methylprop-1-enyl)-4-methylthioazetidin-2- one did not give a corresponding ß-lactam ring expansion product, but gave epimeric 4-chloro-products by replacement of the 4-methylthio-group. 4-Acetoxyazetidin-2-one reacted with chlorosulphonyl isocyanate to give an N-allophanoyl derivative.

M3 - Article

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EP - 822

JO - Journal of the Chemical Society, Perkin Transactions 1

JF - Journal of the Chemical Society, Perkin Transactions 1

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