An interesting route for the synthesis of C-2 substituted cephalosporin sulfones has been described along with an unexpected reactivity on the C-2 carbon of C-2 substituted cephalosporin sulfoxides and sulfones. Thus, bromination of phenoxyacetamidocephemcarboxylate I gave dibromocephem II. Treatment of II with nucleophiles gave C(2)-substitution products III (R = Me, Et, Pr, Me2CH, PhCH2, Ac; n = 0) as a result of dehydrobromination during purifn. Subsequent oxidn. with 3-ClC6H4C(O)OOH gave the title sulfones III (R = Me, Et, Me2CH, PhCH2, Ac; n = 2).

Studies on the synthesis of C-2 substituted cephalosporin sulfones: the unexpected reactivity of the C-2 carbon / M., B., C., C., Saladino, R., R., N.. - In: HETEROCYCLES. - ISSN 0385-5414. - 34:(1992), pp. 1375-1384.

Studies on the synthesis of C-2 substituted cephalosporin sulfones: the unexpected reactivity of the C-2 carbon

SALADINO R;
1992

Abstract

An interesting route for the synthesis of C-2 substituted cephalosporin sulfones has been described along with an unexpected reactivity on the C-2 carbon of C-2 substituted cephalosporin sulfoxides and sulfones. Thus, bromination of phenoxyacetamidocephemcarboxylate I gave dibromocephem II. Treatment of II with nucleophiles gave C(2)-substitution products III (R = Me, Et, Pr, Me2CH, PhCH2, Ac; n = 0) as a result of dehydrobromination during purifn. Subsequent oxidn. with 3-ClC6H4C(O)OOH gave the title sulfones III (R = Me, Et, Me2CH, PhCH2, Ac; n = 2).
1992
cephalosporin sulfones; synthesis; dehydrobromination
01 Pubblicazione su rivista::01a Articolo in rivista
Studies on the synthesis of C-2 substituted cephalosporin sulfones: the unexpected reactivity of the C-2 carbon / M., B., C., C., Saladino, R., R., N.. - In: HETEROCYCLES. - ISSN 0385-5414. - 34:(1992), pp. 1375-1384.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11573/1766488
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