The Synthesis of 3,5‐Diamino‐1,2,4‐oxadiazoles. 1st Communication

Tilley, Jefferson; Ramuz, Henri; Levitan, Paul; Blount, John F.

doi:10.1002/hlca.19800630411

Cited by 25 publications

(8 citation statements)

References 13 publications

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“…Due to their importance, several synthetic methods for preparing the 1,2,4‐oxadiazole ring systems have been reported . The general method for the preparation of 1,2,4‐oxadiazoles is the cyclization of O‐acylamidoximes obtained from acylation of amidoximes with acyl halides, esters or anhydrides .…”

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

ChemistrySelect

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“…The 1,2,4-oxadiazole is known to be readily hydrogenated and to open the ring, 6 whereas catalytic hydrogenation of 9a,b occurred merely at cyano groups to afford corresponding known compounds, 2-amino-1,3,4-oxadiazoles (15a,b), at room temperature under atmospheric pressure, confirming the assignment of 9a,b as rearranged products.…”

mentioning

confidence: 66%

Chlorination and Subsequent Cyclization to 1,3,4-Oxadiazoles of N1-Acyl-N3-cyanoguanidines and Related Compounds

Suzuki¹,

Hasegawa²,

Oda³

et al. 2003

HETEROCYCLES

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N 1 -Acyl-, N 1 -alkoxycarbonyl-, and N 1 -(N,N-dialkylcarbamoyl)guanidines bearing electron-withdrawing cyano or sulfonyl group at the N 3 -position were found to provide corresponding rearranged products, 1,3,4-oxadiazoles, when these guanidines were chlorinated by sodium hypochlorite followed by treating with base. Assignments of obtained compounds were accomplished by means of some reactions such as acid hydrolysis, alkoholysis, and catalytic hydrogenations, and of MS spectra.We previously reported that N 1 -acyl-N 3 -cyanoguanidines reacted with hydroxylamine hydrochloride to afford various type of 1,2,4-oxadiazoles. 1 In this connection, we subsequently investigated the chlorination and cyclization of N 1benzoyl-N 3 -cyanoguanidine in order to obtain 3-cyanoamino-5-phenyl-1,2,4-oxadiazole. However, the product thus obtained was found to be 2-cyanoamino-5-phenyl-1,3,4-oxadiazole. It was also clarified that N 1 -acylguanidines, N 1 -alkoxycarbonylguanidines (N-amidinocarbamates), and N 1 -(N,N-dimethylcarbamoyl)guanidine (1-amidino-3,3dimethylurea) bearing electron-withdrawing cyano or sulfonyl group at the N 3 -position gave corresponding rearranged 1,3,4-oxadiazoles.Fuchigami and Odo first reported in 1974 that treatment of N-benzoyl-N'-chlorobenzamidine with base gave 3,5-diphenyl-1,2,4-oxadiazole. 2 This reaction has been proved to be applicable to N-chloro derivatives of benzoylguanidines (1), 3 alkoxycarbonylguanidines (2), 3 and carbamoylguanidines (3) 4 providing 3-amino-1,2,4-oxadiazoles (4).

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“…The formation of one or other isomer depends on the electronic effect of the substituents in the isothiourea [14,20].…”

Section: Synthesis Of Azolesmentioning

confidence: 99%

Synthesis of azoles and azines and their condensed derivatives based on N-cyano-S-alkylthioureas (Review)

Nekrasov

2007

Chem Heterocycl Comp

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The Synthesis of 3,5‐Diamino‐1,2,4‐oxadiazoles. 1st Communication

Cited by 25 publications

References 13 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

Chlorination and Subsequent Cyclization to 1,3,4-Oxadiazoles of N1-Acyl-N3-cyanoguanidines and Related Compounds

Synthesis of azoles and azines and their condensed derivatives based on N-cyano-S-alkylthioureas (Review)

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