Facile radical mediated synthesis of azetidin-2,3-diones: potential synthons for biologically active compounds

Bari, S. S.; Magtoof, Mehmood S.; Bhalla, Aman

doi:10.1007/s00706-010-0346-9

Cited by 7 publications

(3 citation statements)

References 29 publications

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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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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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“…Till now, our research group has been engaged in the synthesis of selenoalkanoic acids useful as β‐lactam precursors , novel 3‐thio/seleno‐β‐lactams and their Lewis acid mediated functionalization , stereoselective synthesis of cis ‐ and trans ‐3‐alkoxy‐β‐lactams , spirocyclic‐β‐lactams , ( Z )‐ and ( E )‐3‐allylidene‐β‐lactams , 3‐keto‐β‐lactams , bicyclic‐β‐lactams , and 4‐pyrazolyl β‐lactams . Herein, we report the synthesis of novel pyrimidine/pyrazole linked β‐lactams using a facile and efficient methodology.…”

Section: Introductionmentioning

confidence: 99%

Pyrimidine and Pyrazole Linked Azetidin‐2‐ones: Entry to Novel Class of β‐Lactam Heterocycles

Bhalla

Bari

Rathee

et al. 2017

Journal of Heterocyclic Chem

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A novel series of pyrimidine/pyrazole linked β-lactams have been synthesized in excellent yields using a simple and efficient methodology involving conjunction of different heterocyclic substrates. All the new products were characterized on the basis of various spectroscopic techniques viz. FT-IR, 1 H NMR, 13 C NMR, elemental analysis (CHN), 1 H-1 H correlation spectroscopy ( 1 H-1 H COSY) and mass spectrometry (EIMS) in representative cases. Furthermore, theoretical calculations have also been performed on representative compounds and the results were compared with Cefuroxime axetil (a broad spectrum antibacterial agent). The phenomenon of tautomerism was also observed which was confirmed by different NMR experiments (D 2 O exchange study and 1 H-1 H correlation spectroscopy).

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“…Banik et al 29 have recently reported the iodine/bismuth catalyzed synthesis of pyrrole substituted spirocyclic-β-lactams, 2,34,40 (Z)-and (E)-3-allylidene-β-lactams, 41 3-keto-β-lactams 42 and bicyclic-β-lactams. 43 Herein, we report the synthesis of novel monocyclic trans-and cis-3-oxy/thio/seleno-4-pyrazolyl-β-lactams (5, 6).…”

Section: Introductionmentioning

confidence: 99%

Facile synthesis of novel monocyclic trans- and cis-3-oxo/thio/seleno-4-pyrazolyl-β-lactams

Bhalla¹,

Bari²,

Berry³

et al. 2015

Arkivoc

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A facile synthesis of novel monocyclic trans-and cis-3-oxy/thio/seleno-4-pyrazolyl-β-lactams (5, 6) is described. The reaction of 2-methoxy/phenoxy/benzyl/phenylthio/seleno ethanoic acids or acetoxyacetyl chloride 4 with pyrazolyl substituted Schiff′s bases 3a-d using POCl 3 and Et 3 N in refluxing toluene furnished β-lactams (5, 6). These synthesized β-lactams have been characterized by spectroscopic techniques viz. NMR ( 1 H, 13 C and 77 Se), FT-IR, mass spectrometry (EI-MS and HRMS) and elemental analysis. Single crystal X-ray crystallographic study of trans-1-(4′-methoxyphenyl)-3-methoxy-4-(5′-chloro-3′-methyl-1′-phenyl-1H-pyrazol-4′-yl)azetidin-2-one 5p has confirmed the molecular structure and the stereochemical outcome. The cis or trans configuration of β-lactams (5, 6) was assigned with respect to position of C3-H and C4-H.

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Facile radical mediated synthesis of azetidin-2,3-diones: potential synthons for biologically active compounds

Cited by 7 publications

References 29 publications

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

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

Pyrimidine and Pyrazole Linked Azetidin‐2‐ones: Entry to Novel Class of β‐Lactam Heterocycles

Facile synthesis of novel monocyclic trans- and cis-3-oxo/thio/seleno-4-pyrazolyl-β-lactams

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