Thiazolineazetidinone derivatives

Details Thiazolineazetidinone derivatives Thiazolineazetidinone derivatives

1977-12-15

1979-10-23

Rizzo, Nicholas S.

Textiles: cloth finishing

424246, 2602391, 424271, C07D27708

Patent

active

041720784

ABSTRACT:
Thiazolineazetidinone derivatives of the formulae 1,2, and 3. ##STR1## wherein R is derived from the commonly known carboxamido groups present in penicillins, R.sup.1 is a carboxy protecting group commonly used in penicillin chemistry, and R.sup.2 is Cl, Br, I, CN, lower alkoxy, lower acyloxy, SCN, SCH.sub.3, S-phenyl, S-heteroaryl such as 5-mercaptotetrazole or 2-mercapto-5-methyl-1,3,4-thiadiazole, NO.sub.3, N.sub.3, NH-phenyl, and N(CH.sub.3).sub.2 with the proviso that R.sup.2 in the compounds of formula 1 is limited to Cl, Br, I, and lower acyloxy, and a process for preparing said compounds from 2-(substituted methyl) penicillin sulfoxides followed by treatment with a base.
The compounds of formulae 1,2, and 3 are useful as intermediates in the synthesis of cephalosporins.

REFERENCES:
patent: 3862164 (1975-01-01), Cooper
patent: 3880872 (1975-04-01), Kukolja et al.
patent: 3989685 (1976-11-01), Tanida et al.
patent: 4009159 (1977-02-01), Kamiya et al.
patent: 4052408 (1977-10-01), Hensler et al.
patent: 4077970 (1978-03-01), Foglio et al.
Flynn, Cephalosporins and Penicillins, pp. 199-203 (1972).
Tetrahedron Letters No. 13, pp. 975-978 (1976).
Franceschi, JACS, vol. 99, Jan. 9, 1977, pp. 248-250.

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