A Simple and One‐Pot Synthesis of β‐Sultams by Using the Vilsmeier Reagent

Zarei, Maaroof; Jarrahpour, Aliasghar

doi:10.1002/jhet.1630

Cited by 9 publications

(3 citation statements)

References 58 publications

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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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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

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“…Chloromethylenedimethylammonium chloride (Vilsmeier reagent) 2 has been mostly used as an acid activator for the synthesis of esters , amides , β‐sultams , diacylhydrazines , 1,3,4‐oxadiazoles , and β‐lactams .…”

Section: Introductionmentioning

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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“…Chloromethylenedimethylammonium chloride (Vilsmeier reagent) 3 is easily prepared by the reaction of DMF and oxalyl chloride or thionyl chloride in dry dichloromethane [14]. This reagent has been identified as a formylating agent [15], a coupling reagent in the synthesis of esters [16], amides [17], acid chlorides [18], b-sultams [19], b-lactams [20], diacylhydrazines [21], 1,3,4-oxadiazoles [22], and 1,3,4-thiadiazoles [23].…”

Section: Introductionmentioning

confidence: 99%

One-pot Vilsmeier reagent-mediated multicomponent reaction: A direct synthesis of oxazolones and Erlenmeyer azlactones from carboxylic acids

Fadavi¹,

Zarei²

2018

Comptes Rendus. Chimie

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N-Acylation of glycine with carboxylic acids was carried out by using the Vilsmeier reagent. The resulting N-acyl-a-amino acids were subsequently cyclodehydrated into oxazol-5-ones via the Vilsmeier reagent. Finally, treatment of oxazol-5-ones with aldehydes in the presence of the Vilsmeier reagent delivered Erlenmeyer azlactones. By combining these steps, using the Vilsmeier reagent allowed direct one-pot conversion of carboxylic acids into oxazol-5-ones and direct one-pot conversion of carboxylic acids into Erlenmeyer azlactones in the presence of aldehydes. These Vilsmeier reagent-mediated multicomponent reactions proceeded smoothly in reasonable chemical yields at room temperature. The chemical structure of the title compounds was confirmed by spectral data.

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A Simple and One‐Pot Synthesis of β‐Sultams by Using the Vilsmeier Reagent

Cited by 9 publications

References 58 publications

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

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

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

One-pot Vilsmeier reagent-mediated multicomponent reaction: A direct synthesis of oxazolones and Erlenmeyer azlactones from carboxylic acids

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