Seleno-β-lactams: synthesis of monocyclic and spirocyclic selenoazetidin-2-ones

Bhalla, Aman; Venugopalan, Paloth; Bhasin, K. K.; Bari, S. S.

doi:10.1016/j.tet.2007.02.001

Cited by 39 publications

(23 citation statements)

References 62 publications

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“…Thus, the synthesis began with the known starting materials cis-3-chloro-3-benzylseleno-β-lactams (1), which were prepared according to the reported literature procedure [20]. For the synthesis of cis-3-allyloxy-3-benzylseleno-β-lactams (3), the β-lactam carbocation equivalent 1 was treated with allyl alcohol (2) in the presence of Lewis acid ZnCl 2 /silica gel (100-200 mesh) in dry chloroform, under nitrogen atmosphere, at reflux temperatures by the route outlined in Scheme-I.…”

Section: Resultsmentioning

confidence: 99%

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Synthesis of Novel 4-Halomethyl-1,3-oxaselenolane Substituted Spirocyclic Azetidin-2-ones from cis-3-Allyloxy-3-benzylselenoazetidin-2-ones

Narula¹,

Bari²,

Banik³

et al. 2017

Asian J. Chem.

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A mild and efficient synthetic approach for the synthesis of novel 4-halomethyl-1,3-oxaselenolane substituted spirocyclic β-lactams via intraselenyl cyclization of cis-3-allyloxy-3-benzylselenoazetidin-2-one mediated by halogens (I2, Br2) is described. The mechanism involves step-wise electrophilic addition-dealkylation sequence generating spiroseleno-β-lactams stereospecifically. The novel synthesized β-lactams have been characterized by spectroscopic techniques viz. NMR ( 1 H, 13 C, 77 Se), FT-IR and elemental analysis. The cis configuration of the nucleophilic substituent at C-3 was assigned with respect to C4-H. Intraselenyl cyclization is a novel approach in the chemistry of β-lactam research.

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Section: Resultsmentioning

confidence: 99%

“…General procedure: The synthesis of compound 1 and its spectroscopic data has been described previously [20].…”

Section: Synthesis Of Novel 4-halomethyl-13-oxaselenolane Substitutementioning

confidence: 99%

Synthesis of Novel 4-Halomethyl-1,3-oxaselenolane Substituted Spirocyclic Azetidin-2-ones from cis-3-Allyloxy-3-benzylselenoazetidin-2-ones

Narula¹,

Bari²,

Banik³

et al. 2017

Asian J. Chem.

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“…30,31 The products obtained in good to excellent yields were having cis configuration of hydrogen atoms at C-3/C-4. …”

Section: Methodsmentioning

confidence: 97%

Advances in synthesis of monocyclic beta-lactams

Singh¹,

Sudheesh²

2014

Arkivoc

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Recent years have witnessed significant advancement in cycloaddition and cyclization strategies for the synthesis of monocyclic β-lactams. Cycloadditions include the Staudinger's keteneimine cycloaddtions and related reaction. Cyclization reactions are reported to furnish β-lactams through N 1 -C 2 , N 1 -C 4 and C 3 -C 4 bond formations employing substrates like β-amino esters, β-amino alcohols, β-hydroxamate esters, and α-amino diazocarbonyls, etc. Some other strategies are silyl carbonylation reactions, ring-enlargement of aziridines, cleavage of one ring of a bicyclic β-lactam, and functional group transformations on the β-lactam rings. Recently, some multi-component reactions have also been designed. This article reviews the advances made in synthetic approaches to monocyclic β-lactams during last five years.

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“…In our earlier studies, we have demonstrated the synthesis of selenoalkanoic acids useful as β-lactam precursors [31,32], novel 3-thio/seleno β-lactams and Lewis acid mediated functionalization [33][34][35][36][37][38][39], stereoselective cis-and trans-3-alkoxy-β-lactams [40], spirocyclic β-lactams [35,[41][42], (Z)-and (E)-3-allylidene-β-lactams [43], 3-keto-β-lactams [44] and bicyclic-β-lactams [45]. Recently, hybrid β-lactams I, II, III (Figure 1) with varied heterocyclic moieties have been shown to exhibit antimicrobial, antiprotozoal, anti-inflammatory and analgesic activities [46][47][48].…”

Section: Canadian Chemical Transactionsmentioning

confidence: 99%

Synthesis of Novel Pyrazolylmethylene-Pyrimidine Heterocycles: Potential Synthons for Hybrid Β-Lactams

2015

Can Chem Trans

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Diversely substituted novel pyrazolylmethylene-pyrimidine heterocycles were synthesized via Knoevenagel condensation between substituted formyl pyrazoles and barbituric acids without any base or solid catalyst. All these thirteen novel heterocycles were characterized by FT-IR, NMR spectroscopy ( 1 H, 13 C), 13 C DEPT-135, 1 H- 13C HSQC, elemental analysis and mass spectrometry (in representative case).

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Seleno-β-lactams: synthesis of monocyclic and spirocyclic selenoazetidin-2-ones

Cited by 39 publications

References 62 publications

Synthesis of Novel 4-Halomethyl-1,3-oxaselenolane Substituted Spirocyclic Azetidin-2-ones from cis-3-Allyloxy-3-benzylselenoazetidin-2-ones

Synthesis of Novel 4-Halomethyl-1,3-oxaselenolane Substituted Spirocyclic Azetidin-2-ones from cis-3-Allyloxy-3-benzylselenoazetidin-2-ones

Advances in synthesis of monocyclic beta-lactams

Synthesis of Novel Pyrazolylmethylene-Pyrimidine Heterocycles: Potential Synthons for Hybrid Β-Lactams

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