Regioselective Epimerisation of cis-3-Amino-4-oxo-azetidine-2-sulphonic acid and Synthesis of Monocyclic β-Lactams

Cerić, Helena; Kovačević, Miće; Šindler‐Kulyk, Marija

doi:10.1016/s0040-4020(00)00298-2

Cited by 11 publications

(3 citation statements)

References 7 publications

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“…The stereochemistries of cis-/trans-isomers were determined using the chemical shift values (δ) and coupling constants (J ) of C(3)H and C(4)H signals in 1 H NMR. 21,22 Accordingly, we investigated the ratios of cis-/trans-isomer formed in different reaction conditions, and the results were shown in Table 1.…”

Section: Resultsmentioning

confidence: 99%

Studies on the Design and Synthesis of New Monocyclic β-Lactams Containing Substructures of Penicillin G

Lee

2014

Bulletin of the Korean Chemical Society

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The studies on design and synthesis of new monocyclic β-lactam esters 4(R/S)-(1'-methoxycarbonylpropyl-2'(R/S)-thio)-3(R)-phenylacetamidoazetidin-2-one (3a) and 4(R/S)-(1'-methoxycarbonyl-2'-methyl-propyl-2'-thio)-3(R)-phenylacetamidoazetidin-2-one (3b) were described. Compounds 3a and 3b were specifically designed to retain all penicillin substructures except the bicyclic system, which would be conceived by cleaving the C(3)-N(4) bond of penicillin G. Compounds 3a and 3b are of particular interest in the context of the structural elucidation of monocyclic β-lactams originated from penicillin. Key intermediates, β-mercapto esters 6a and 6b, were synthesized from conjugate acids 4a and 4b using three-step synthetic sequences, respectively, and 4(S)-acetoxy-3(S)-phenylacetamidoazetidin-2-one (7) was obtained from the degradation of penicillin G. Reactions of 6a and 6b with 7, thus obtained, provided the target compounds 3a and 3b, respectively.

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Section: Resultsmentioning

confidence: 99%

Studies on the Design and Synthesis of New Monocyclic β-Lactams Containing Substructures of Penicillin G

Lee

2014

Bulletin of the Korean Chemical Society

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“…There are only a few reports of the isolation of these types of products [16][17][18] and only a single remotely related structure has been described. 19 Terminal sulfimic acid moieties and their carbamoylsulfimidate derivatives similar to 1 do not seem to have been reported.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of reduction-sensitive 1,1-diarylhydrazines from 1,1-diarylamines

et al. 2014

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1-(2-Nitrophenyl)-1-phenylamine and methyl 4-((2-nitrophenyl)amino)benzoate have been transformed into their corresponding urea derivatives through the action of chlorosulfonyl isocyanate. The initial sulfimidate product from the former reaction has sufficient stability so that it can be isolated and characterized as its disodium salt, and this, as well as three other subsequent products, have been characterized by X-ray diffraction. The corresponding intermediary urea was converted into its hydrazine derivative via a Hofmann rearrangement under oxidative conditions. Density functional theory has been used to examine the nature of the intermediates and transition states for the Hofmann rearrangement. There is little theoretical indication for a cyclic aziridinonium intermediate and the transition state between the urea and the isocyanate corresponds to a reactant-like rotation of the planar singlet nitrene before migration and formation of the new N−N bond.Résumé : La 1-(2-nitrophényle)-1-phénylamine et la 4-((2-nitrophényle)amino)benzoate de méthyle ont été transformé par leur réaction avec l'isocyanate de chlorosulfonyle en leurs urées correspondantes. Dans le premier cas, le produit initial de cette réaction, un sulfimidé, démontre une stabilité qui permet son isolement comme sel de sodium. Celui-ci ainsi que trois produits ultérieurs ont été caractérisés par diffraction de rayons X. L'urée de 1-(2-nitrophényle)-1-phénylamine a été transformé en hydrazine par réarrangement de Hofmann sous conditions oxydatives. La théorie de la fonctionnelle de la densité a été utilisé afin d'examiner les intermédiaires et les états de transition de ce réarrangement. Les calculs indiquent qu'un intermédiaire aziridononium cyclique est peu probable et que l'état de transition qui mène de l'urée à l'isocyanate et finalement à l'hydrazine correspond à une rotation de la nitrène planaire de forme singulet avant sa migration et la formation d'une nouvelle liaison entre les deux atomes d'azote.

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“…On the other hand, I also intended to choose an appropriate acid as an acyl side chain. Among numerous acids, aminothiazole moieties have been extensively explored, and in particular, 2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetic acid (15) has been widely employed in clinically important β-lactam antibiotics 19 and in investigations of structure-activity relationships. 20 Based on this fact, I chose 15 as an exemplary acid for our study.…”

Section: Design and Synthesis Of New 4-alkylthio Monocyclic β-Lactamsmentioning

confidence: 99%

Design and Synthesis of New 4-Alkylthio Monocyclic β-Lactams

Lee

2013

Bulletin of the Korean Chemical Society

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New types of monocyclic β-lactams constitute an important class of compounds due to their unique structures and natures. Here, the design and synthesis of new 4-alkylthio monocyclic β-lactams 2a and 3a are reported. Significantly, compounds 2a and 3a, while keeping a monocyclic system, were designed to contain all of the substructures provided by the cleavage of C(2)-C(3) bond in penicillins. Efficient synthetic pathways for compounds 2a and 3a were established based on two different strategies. Compound 2a was synthesized from raw materials, using 4-acetoxyazetidin-2-one as a key intermediate, through a ten-step synthetic sequence in 3% overall yield. Compound 3a was synthesized from potassium salt of penicillin G (17), using the degraded product 20 as a key intermediate, through a six-step synthetic sequence in 11% overall yield. 4-Alkylthioazetidin-2-one derivatives, introduced in this study, could serve as valuable intermediates for the development of new monocyclic β-lactams.

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Regioselective Epimerisation of cis-3-Amino-4-oxo-azetidine-2-sulphonic acid and Synthesis of Monocyclic β-Lactams

Cited by 11 publications

References 7 publications

Studies on the Design and Synthesis of New Monocyclic β-Lactams Containing Substructures of Penicillin G

Studies on the Design and Synthesis of New Monocyclic β-Lactams Containing Substructures of Penicillin G

Synthesis of reduction-sensitive 1,1-diarylhydrazines from 1,1-diarylamines

Design and Synthesis of New 4-Alkylthio Monocyclic β-Lactams

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