Penicillin-cephalosporin conversion IV. Direct synthesis of 3'-thiosubstituted cephalosporins from thiazoline-azetidinones

Sigeru Torii; Hideo Tanaka; Michio Sasaoka; Norio Saitoh; Takashi Siroi; Junzo Nokami

doi:10.1016/S0040-4039(00)87378-5

Penicillin-cephalosporin conversion IV. Direct synthesis of 3'-thiosubstituted cephalosporins from thiazoline-azetidinones

Sigeru Torii, Hideo Tanaka, Michio Sasaoka, Norio Saitoh, Takashi Siroi, Junzo Nokami

Faculty of Engineering

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

1 Citation (Scopus)

Abstract

Direct transformation of thiazoline-azetidinones 2, derived from penicillin G and V, into 3′-thio-substituted cephalosporins 4 has been performed by ring opening of the thiazoline moiety with sulfenyl chlorides followed by ring closure with NH₃ in dimethylformamide and simultaneous displacement of the allylic chlorine atom with the leaving thiolates.

Original language	English
Pages (from-to)	2495-2498
Number of pages	4
Journal	Tetrahedron Letters
Volume	23
Issue number	24
DOIs	https://doi.org/10.1016/S0040-4039(00)87378-5
Publication status	Published - 1982

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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abstract = "Direct transformation of thiazoline-azetidinones 2, derived from penicillin G and V, into 3′-thio-substituted cephalosporins 4 has been performed by ring opening of the thiazoline moiety with sulfenyl chlorides followed by ring closure with NH3 in dimethylformamide and simultaneous displacement of the allylic chlorine atom with the leaving thiolates.",

author = "Sigeru Torii and Hideo Tanaka and Michio Sasaoka and Norio Saitoh and Takashi Siroi and Junzo Nokami",

year = "1982",

doi = "10.1016/S0040-4039(00)87378-5",

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AU - Torii, Sigeru

AU - Tanaka, Hideo

AU - Sasaoka, Michio

AU - Saitoh, Norio

AU - Siroi, Takashi

AU - Nokami, Junzo

PY - 1982

Y1 - 1982

N2 - Direct transformation of thiazoline-azetidinones 2, derived from penicillin G and V, into 3′-thio-substituted cephalosporins 4 has been performed by ring opening of the thiazoline moiety with sulfenyl chlorides followed by ring closure with NH3 in dimethylformamide and simultaneous displacement of the allylic chlorine atom with the leaving thiolates.

AB - Direct transformation of thiazoline-azetidinones 2, derived from penicillin G and V, into 3′-thio-substituted cephalosporins 4 has been performed by ring opening of the thiazoline moiety with sulfenyl chlorides followed by ring closure with NH3 in dimethylformamide and simultaneous displacement of the allylic chlorine atom with the leaving thiolates.

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ER -

Penicillin-cephalosporin conversion IV. Direct synthesis of 3'-thiosubstituted cephalosporins from thiazoline-azetidinones

Abstract

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