The Vilsmeier reagent: a useful and versatile reagent for the synthesis of 2-azetidinones

Jarrahpour, Aliasghar; Zarei, Maaroof

doi:10.1016/j.tet.2009.02.005

Cited by 64 publications

(17 citation statements)

References 56 publications

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“…Thin‐layer chromatography was carried out on silica gel 254 analytical sheets obtained from Fluka. (Chloromethylene)dimethylammonium chloride (Vilsmeier reagent) 2 was obtained as a white solid by a reported procedure . Schiff bases 5 were prepared according to reported methods, and their spectral data have been previously reported .…”

Section: Methodsmentioning

confidence: 99%

Synthesis of Novel β‐Lactams from Phenothiazin‐10‐ylacetic Acid

Omidvari

Zarei

2018

Journal of Heterocyclic Chem

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The first synthesis of 3‐phenothiazine‐β‐lactams is herein reported. Thirteen new derivatives of β‐lactams were synthesized using various Schiff bases and (phenothiazin‐10‐yl)acetic acid, which in turn was prepared starting from phenothiazine. The sole product of the Staudinger ketene–imine [2 + 2] cycloaddition reaction is the trans‐β‐lactam. All the synthesized compounds were characterized by elemental analyses and spectral (IR, 1H‐NMR, and 13C‐NMR) data.

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Section: Methodsmentioning

confidence: 99%

Synthesis of Novel β‐Lactams from Phenothiazin‐10‐ylacetic Acid

Omidvari

Zarei

2018

Journal of Heterocyclic Chem

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“…Vilsmeier reagent offers several advantages such as broad functional group tolerance, easy workup due to water‐soluble by‐products and high yield and purity of products. Although Vilsmeier reagent has been primarily used as formylating agent, a new applications have been recently developed for this reagent, for example, coupling reagent in the synthesis of esters, amides, acid chlorides, β‐sultams, β‐lactams, diacylhydrazines, 1,3,4‐oxadiazoles, 1,3,4‐thiadiazoles, oxazolones and Erlenmeyer azlactones . It is easily prepared by reaction of DMF and oxalyl chloride or thionyl chloride in dry dichloromethane …”

Section: Introductionmentioning

confidence: 99%

A Mild and Efficient One‐Pot Preparation of 1,2,4‐Oxadiazoles from Nitriles and Carboxylic Acids Using Vilsmeier Reagent

Zarei

2018

ChemistrySelect

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A one-pot synthesis of 1,2,4-oxadiazoles has been achieved from the corresponding amidoximes and carboxylic acids or from nitriles, hydroxylamine and carboxylic acids, employing the OH activation property of the Vilsmeier reagent. The precursor O-acylamidoxime could be derived in situ which underwent an intramolecular cyclization in the presence of Vilsmeier reagent to afford 1,2,4-oxadiazole. The products were simply obtained in good to excellent yields under mild condition and compatible with a range of functional groups. Utilization of easy workup and purification of products make it very interesting.

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“…The different biological activities reported for azetidinones are thrombin and chymase inhibitory activity, 12 anti‐parkinsonian, 13 anti‐fungal, 14 anti‐bacterial, 15 anti‐convulsant, 16 anti‐colorectal cancer agents, 17 Cathepsin K inhibitors, and vasopressin inhibitors, 18 cholesterol absorption inhibitory activity, 19 tryptase inhibitors, 20 etc. Literature also reported different reagents for design and synthesis of lactum ring 21–25 . Apart from their clinical use, these compounds have been used as synthons in the preparation of various heterocyclic compounds of biological significance.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization and antibacterial activity of 1‐([6‐bromo‐2‐hydroxy‐naphthalen‐1‐yl]arylphenyl)methyl)‐3‐chloro‐4‐(arylphenyl)‐azetidin‐2‐one

Chopde

Pandhurnekar²,

Yadao

et al. 2020

Journal of Heterocyclic Chem

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One‐pot synthesis of 1‐([6‐bromo‐2‐hydroxy‐naphthalen‐1‐yl]‐aryl‐phenyl)methyl)‐3‐chloro‐4‐(aryl‐phenyl)azetidin‐2‐ones has been reported in the present research work via Staudinger [2 + 2] ketene‐imine cycloaddition reaction pathway. The reaction of 1‐((Benzylideneamino)(aryl)methyl)‐6‐bromo‐naphthalen‐2‐ols with chloroacetic acid and triethylamine afforded 1‐([6‐bromo‐2‐hydroxynaphthalen‐1‐yl]aryl‐phenyl)methyl)‐3‐chloro‐4‐(aryl‐phenyl)azetidin‐2‐ones. For the structural elucidation of series of compounds, different analytical and spectroscopic techniques such as elemental analysis, IR spectra, 1H‐NMR spectra and mass spectra were used. All the newly synthesized compounds were tested for their anti‐bacterial activity studies. It revealed that some of the compounds possesses moderate to good activities as compared to standard drugs. The widest spectrum of anti‐bacterial activities against both gram‐positive and gram‐negative bacterial strains among the examined compounds possessed having more hydroxyl group along with β‐lactam ring compared to other substituted azetidinones.

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The Vilsmeier reagent: a useful and versatile reagent for the synthesis of 2-azetidinones

Cited by 64 publications

References 56 publications

Synthesis of Novel β‐Lactams from Phenothiazin‐10‐ylacetic Acid

Synthesis of Novel β‐Lactams from Phenothiazin‐10‐ylacetic Acid

A Mild and Efficient One‐Pot Preparation of 1,2,4‐Oxadiazoles from Nitriles and Carboxylic Acids Using Vilsmeier Reagent

Synthesis, characterization and antibacterial activity of 1‐([6‐bromo‐2‐hydroxy‐naphthalen‐1‐yl]arylphenyl)methyl)‐3‐chloro‐4‐(arylphenyl)‐azetidin‐2‐one

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