Reactions of mercapto amino acids

Knunyants, I. L.; Kil'disheva, O. V.; Krasuskaya, M. P.; Lin'kova, M. G.; Shokina, V. V.; Benevolenskaya, Z. V.; Rasteikene, L. P.

doi:10.1007/bf00912106

Cited by 3 publications

(2 citation statements)

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“…yield, was then cyclized (9,10) in a solution of methanol saturated with ammonia to yield 49% of 3-carboxy-5-oxoperhydro-1,4-thiazepine (6). Esterification of the acid 6, effected by standard treatment with ethereal diazomethane, gave a nearly quantitative yield of the desired ester 7.…”

Section: Synthesismentioning

confidence: 99%

“…Although there are reports, of attempts to achieve such a goal by Knunyants and coworkers (6) and also by Leonard and Wilson (7), this synthetic approach has never been thoroughly investigated due mainly to the unavailability 'NRCC Predoctorate Fellow 1965. 'NRCC Predoctorate Fellow 1968-1971 3The terms "penam" and "penicillanic acid" correspond t o the following ring systems and carry n o stereochemical implications, as first suggested by Sheehan et al (21).…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of Some Stable 7-Halo-1,4-thiazepines. Potential Substituted Penam Precursors

Blondeau¹,

Berse²,

Gravel³

1971

Can. J. Chem.

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The synthesis of some new 3-carbomethoxy-5-oxoperhydro-1,4-thiazepines is described. Halogenation studies led to the preparation of three potential substituted penam ring precursors: 6,7-dibromo-3-carbomethoxy-5-oxoperhydro-1,4-thiazepine, 3-carbomethoxy-6,7-dichloro-5-oxoperhydro-1,4-thiazepine, and 3-carbomethoxy-7-chloro-6,6-dimethyl-5-oxoperhydro-1,4-thiazepine. Preliminary studies on the reactivity of these a-halothioethers showed that methanolysis to the corresponding methoxy-thiazepines may be carried out in nearly quantitative yields in the case of the first two derivatives; the third compound, on the other hand, led to an open-chain dehydrohalogenated product where C-7 is converted to the corresponding dimethyl acetal.La synthkse de quelques nouvelles methoxycarbonyl-3 0x0-5 perhydrothiazepines-1,4 est rapportee. Des etudes sur I'halogtnation de ces composes ont conduit a la preparation de trois precurseurs possibles du noyau penam substitue: la dibromo-6,7 mCthoxycarbony1-3 0x0-5 perhydrothiazCpine-1,4, la dichloro-6,7 methoxycarbonyl-3 0x0-5 perhydrothiazepine-l,4, et la chloro-7 dimethyl-6,6 mCthoxycarbony1-3 0x0-5 perhydrothiazepine-l,4. Des etudes preliminaires sur la rtactivite de ces a-halogCnothioethers ont montre que, dans le cas des deux premiers derives, la mkthanolyse pour donner les mCthoxy thiaztpines correspondantes peut Ctre effectuee avec des rendements quasi-quantitatifs; le troisieme compos6, d'autre part, a conduit a un produit de dtshydrohalogenation oh le C-7 est transforme en dimethyl ac6tal correspondant.

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Section: Synthesismentioning

confidence: 99%