Studies on β-lactam antibiotics. I. A novel conversion of penicillins into cephalosporins
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Summary
A novel conversion of penicillins into cephalosporins through these important key intermediates is reported, finding that dithioazetldinones (II) easily obtained from reactions ofPenicillin sulfoxides (I) with heteroaromatic thiols, are the key intermediate for preparing 2-halomethyl-penams and cephams (IV) derivatives.
- Type
- article
- Published
- 1973-01-01
- Cited by
- 35
- References
- 7
- OpenAlex
- https://openalex.org/W1986515168
- Semantic Scholar
- https://api.semanticscholar.org/CorpusID:93188525
Keywords
Chemistry, Cephalosporin, Lactam, Antibiotics, Cephalosporin Antibiotic
References
- ORGANIC DISULFIDES AND RELATED SUBSTANCES .35. PREPARATION OF UNSYMMETRICAL DISULFIDES CONTAINING CARBOXYLATE MOIETIES AND NEIGHBORING-GROUP EFFECTS OF SULFINATE AND CARBOXYLATE MOIETIES ON DISPROPORTIONATION
- Structural studies on penicillin derivatives. I. The configuration of phenoxymethyl penicillin sulfoxide.
- Stereoisomerism of penicillin sulfoxides
- Structural studies on penicillin derivatives. V. Penicillin sulfoxide-sulfenic acid equilibrium.
- Thiiranium Ions as Reaction Intermediates
- Organic disulfides and related substances. XXXI. Possible anchimeric involvement of an ortho carboxylate moiety in disproportionation of unsymmetrical o-carboxyphenyl disulfides
Cited by
- Recent Advances in the Chemistry and Biochemistry of β-Lactams as β-Lactamase Inhibitors
- Synthesis of (5R)-(Z)-6-(1-methyl-1,2,3-triazol-4-ylmethylene)penem-3-carboxylic acid, a potent broad spectrum β-lactamase inhibitor, from 6-aminopenicillanic acid
- Transformations of thiopyrimidine and thiopurine nucleosides following oxidation with dimethyldioxirane
- TRANSFORMATION OF PENICILLINS INTO 3-SUBSTITUTED DELTA 3-CEPHEMS THROUGH ADDITION/CYCLIZATION OF ALLENECARBOXYLATES
- Preparation of delta 3-7 alpha-phenylacetamidodesacetoxycephalosporanic acid.
- Chemistry and Synthesis of Some Novel β-Lactam Antibiotics and . beta.-Lactamase Inhibitors
- Solid-phase synthesis of 2β-methyl substituted penam derivatives through penicillin sulfoxide rearrangement
- Carbon nucleophilic displacements on kamiya's azetidinone disulfide: Synthesis of c-2 modified penicillins
- THE CHEMISTRY OF OPTICALLY ACTIVE SULFUR COMPOUNDS PART III
- Reactions of Disulfides Derived from Penicillin Sulfoxides with Tertiary Phosphines in Presence of Carboxylic Acids
- Synthese neuer β–Lactam–Antibiotica
- Synthesis of disulfides via sulfenylation of alkyl and aryldithiopyridine n-oxides
- Intramolecular sulfoxide electrophilic sulfenylation in 2- and 3-indoleanilides
- Facile Synthesis of Trisubstituted Thioindoles via a Novel Tricyclic Thiolactone Intermediate
- Desulphurative approaches to penem antibiotics. I. 4-acyldithioazetidin-2-ones via thermolysis of penicillin-derived sulphoxides
- A solid- and solution-phase-based library of 2β-methyl substituted penicillin derivatives and their effects on growth inhibition of tumor cell lines
- Prominent Aspects of Electroorganic Synthesis in β‐Lactam Chemistry
- STUDIES ON BETA‐LACTAM ANTIBIOTICS PART 1, A NOVEL CONVERSION OF PENICILLINS INTO CEPHALOSPORINS
- Rearrangements of penicillanic acid derivatives
- Efficient Synthesis of Unsymmetrical Disulfides through Sulfenic Acids
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