75655-52-6

Usage

Family

Oxadiazole

Biological and pharmacological activities

Yes

Physical appearance

White crystalline powder

Usage

Research and development of pharmaceuticals and agrochemicals

Potential

Building block in the synthesis of various bioactive molecules

Structural features

Interesting candidate for drug design and discovery

Scientific community interest

Further exploration and potential commercialization

Upstream product

• 40016-10-2 N'-pivaloylbenzohydrazide 
• 613-94-5 benzoic acid hydrazide 
• 75-98-9 Trimethylacetic acid 
• 3282-30-2 pivaloyl chloride 
• 65-85-0 benzoic acid 
• 630-19-3 pivalaldehyde 
• 77420-83-8 N′-(2,2-dimethylpropylidene)benzohydrazide 

Relevant academic research and scientific papers

Iron(III)/TEMPO-Catalyzed Synthesis of 2,5-Disubstituted 1,3,4-Oxadiazoles by Oxidative Cyclization under Mild Conditions

A simple and efficient cationic Fe(III)/TEMPO-catalyzed oxidative cyclization of aroyl hydrazones has been developed for the synthesis of 2,5-disubstituted 1,3,4-oxadiazole derivatives. The reaction offers a broad scope, good functional-group tolerance, and high yields under mild conditions in the presence of O 2.

A process for preparing 2, 5 - disubstituted - 1, 3, 4 - oxadiazoles (by machine translation)

The invention provides a method for catalytic oxidative cyclization of formula (II) is shown in the 1, 3, 4 - oxadiazole method, said method comprising: in order to having a structure of formula (I) indicated by the formyl zong compound as a raw material, in order to air or oxygen atmosphere, in order to nitric acid the iron is catalyst, in order to 2, 2, 6, 6 - tetramethyl piperidine nitrogen oxides as initiator, under the action of the water absorbing agent, under the action of the water absorbing agent, in an organic solvent, for 25 - 60 °C lower reaction 3 - 12h, and the resulting reaction solution by the following formula (II) after treatment indicated by the 1, 3, 4 - oxadiazole compounds; the reaction of the invention speed, mild condition, easy operation, low cost, safe reaction, the whole process is friendly to the environment, pollution-free. (by machine translation)

Visible-light-promoted aerobic oxidative cyclization to access 1,3,4-oxadiazoles from aldehydes and acylhydrazides

A novel and practical access to symmetrical and unsymmetrical 2,5-disubstituted 1,3,4-oxadiazoles directly from aldehydes and acylhydrazides using visible light irradiation under an air atmosphere in the presence of eosin Y as an organophotoredox catalyst at rt is reported. This is the first example of oxidative cyclization of acylhydrazones employing air and visible light as inexpensive, readily available, non-toxic, and sustainable reagents.

I2-mediated oxidative C-O bond formation for the synthesis of 1,3,4-oxadiazoles from aldehydes and hydrazides

A practical and transition-metal-free oxidative cyclization of acylhydrazones into 1,3,4-oxadiazoles has been developed by employing stoichiometric molecular iodine in the presence of potassium carbonate. The conditions of this cyclization reaction also work well with crude acylhydrazone substrates obtained from the condensation of aldehydes and hydrazides. A series of symmetrical and asymmetrical 2,5-disubstituted (aryl, alkyl, and/or vinyl) 1,3,4-oxadiazoles can be conveniently generated in an efficient and scalable fashion.

Synthesis of 1,3,4-oxadiazoles from 1,2-diacylhydrazines using [Et 2NSF2]BF4 as a practical cyclodehydration agent

The preparation of 1,3,4-oxadiazoles from 1,2-diacylhydrazines using XtalFluor-E ([Et2NSF2]BF4) as cyclodehydration reagent is described. Various functionalized 1,3,4-oxadiazoles were synthesized and it was found that the use of acetic acid as an additive generally improved the yields.

Mild and convenient one-pot synthesis of 1,3,4-oxadiazoles

A mild, general, convenient, and efficient one-pot synthesis of 2-phenyl-5-substituted-1,3,4-oxadiazoles is described. Both (hetero)aryl and alkyl carboxylic acids were efficiently condensed with benzohydrazide in the presence of TBTU to give diacylhydrazine intermediates. The latter underwent a smooth TsCl-mediated cyclodehydration reaction to afford 2-phenyl-5-substituted- 1,3,4-oxadiazoles in good to very good yields.

A mild and efficient one pot synthesis of 1,3,4-oxadiazoles from carboxylic acids and acyl hydrazides

A convenient one pot method for the synthesis of 2,5-disubstituted 1,3,4-oxadiazoles from acids and acyl hydrazides is reported. Acid activation with CDI, followed by coupling with the desired acylhydrazide and dehydration in the same pot with Ph3P and CBr4 affords the corresponding 1,3,4-oxadiazoles in good yield. The scope of the acid and acylhydrazide components is presented.

A mild method for the preparation of 1,3,4-oxadiazoles: Triflic anhydride promoted cyclization of diacylhydrazines

Diacylhydrazines undergo cyclization upon treatment with triflic anhydride and pyridine to form the corresponding 1,3,4-oxadiazoles in yields ranging from 70-95%.

2-Chloro-1,3-dimethylimidazolinium chloride. 2. Its application to the construction of heterocycles through dehydration reactions

2-Chloro-1,3-dimethylimidazolinium chloride (DMC) (1) can act as a powerful dehydrating equivalent to DCC (2) under nearly neutral conditions. Its application to the construction of heterocycles through dehydration reactions is described.

DISILYLATED COMPOUNDS AS PRECURSORS OF HETEROCYCLES: A NEW AND EASY OXADIAZOLE SYNTHESIS

Silyl diacylhydrazines have been synthesized.When they are treated with a slight amount of a variety of catalyst (nucleophiles, F-, true or Lewis acids, Pd, Pt...), 1,3,4-oxadiazoles are obtained.This cyclization can be performed in one step by