An Expeditious and Convenient One Pot Synthesis of 2,5-Disubstituted-1,3,4-oxadiazoles

Mashraqui, Sabir H.; Ghadigaonkar, Shailesh G.; Kenny, Rajesh S.

doi:10.1081/scc-120021845

Cited by 61 publications

(14 citation statements)

References 13 publications

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“…A convenient, one-pot procedure has been reported by Mashraqui and coworkers for the synthesis of various 2,5-disubstituted-1,3,4-oxadiazoles 625 by condensing mono-aryl hydrazides 622 with acid chlorides 623 in HMPA solvent under microwave heating (involving as intermediates diaroylhydrazines 624) (Scheme 13.198) [521].…”

Section: Cyclization Of Diacylhydrazinesmentioning

confidence: 99%

Oxadiazoles

Romeo¹,

Chiacchio²

2011

Modern Heterocyclic Chemistry

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Section: Cyclization Of Diacylhydrazinesmentioning

confidence: 99%

Oxadiazoles

Romeo¹,

Chiacchio²

2011

Modern Heterocyclic Chemistry

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“…The results presented in Tables 33 and 34, demonstrate the great im- provement in terms of yields and reaction times, achieved by utilizing this novel method. A convenient one pot method for the synthesis of 1,3,4-oxadiazoles without an acid catalyst or dehydrating agent was developed by Mashraqui et al [84]. The starting monoarylhydrazides 228 were first condensed with acid chlorides 229 in hexamethylphosphoramide at room temperature.…”

Section: B) Advances In Microwave-assisted and Solid Phase Chemistrymentioning

confidence: 99%

Recent Advances in the Synthesis of 1,2,4- and 1,3,4-Oxadiazoles

Jakopin¹,

Dolenc

2008

COC

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The synthesis of peptidomimetics is an area of research that has gained a lot of attention in recent years. Peptidomimetics are compounds designed to mimic the natural peptide but retain its activity with increased stability and bioavailibility, as a result of the structural changes introduced into the parent molecule. The most frequent of these changes are peptide bond surrogates, which contribute to the hydrolytic resistance of peptidomimetics. 1,2,4-and 1,3,4-oxadiazoles are commonly employed as bioisosteric replacements of the amide bond thus constituting these heterocycles as an important structural motif for the pharmaceutical industry.The article will therefore provide an insight into the synthetic methodologies leading to 1,2,4-and 1,3,4-oxadiazole formation to give the reader an appreciation of the field. This review covers all recent developments achieved in the classical synthesis. Additionally, it focuses on the emerging methodologies of microwave-assisted and solid phase synthesis, thus revealing the scope of influence that these methodologies have in the synthesis of 1,2,4-and 1,3,4-oxadiazoles.

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“…The most general method involves the cyclization of diacylhydrazides with a variety of reagents, such as thionyl chloride, phosphorus oxychloride, or sulfuric acid, usually under harsh reaction conditions. Few reliable and operationally simple examples have been reported for the one-step synthesis of 1,3,4-oxadiazoles, especially from readily available carboxylic acids and acid hydrazides [16][17][18][19][20][21].…”

Section: Introductionmentioning

confidence: 99%