10465-97-1

Upstream product

• 65-85-0 benzoic acid 
• 93-58-3 benzoic acid methyl ester 
• 4231-62-3 1-benzoyl-1H-benzotriazole 
• 4114-31-2 ethylhydrazine carboxylate 
• 55084-83-8 2-phenyl-4-ethoxycarbonyl-1,3,4-oxadiazol-5(4H)-one 
• 541-41-3 chloroformic acid ethyl ester 
• 613-94-5 benzoic acid hydrazide 
• 618-32-6 Benzoyl bromide 
• 10465-85-7 benzoyl-diazenecarboxylic acid ethyl ester 

Downstream Products

• 24028-40-8 5-phenyl-1,3,4-thiadiazolin-2-one 
• 5585-19-3 2-phenyl-1,3,4-thiadiazole-5(4H)-thione 
• 1925-70-8 5-phenyl-1,3,4-thiadiazole-2(3H)-thione 
• 1148-89-6 2-phenylamino-5-phenyl-1,3,4-oxadiazole 
• 5262-95-3 2-phenyl-5-(piperidin-1-yl)-1,3,4-oxadiazole 
• 23767-52-4 benzyl(5-phenyl-1,3,4-oxadiazol-2-yl)amine 
• 23767-47-7 2-phenyl-5-(pyrrolidin-1-yl)-1,3,4-oxadiazole 
• 23767-49-9 2-(morpholin-4-yl)-5-phenyl-1,3,4-oxadiazole 
• 23767-50-2 2-(4-methylpiperazin-1-yl)-5-phenyl-1,3,4-oxadiazole 
• 1156534-51-8 2-ethoxy-5-phenyl-1,3,4-selenadiazole 
• 74752-53-7 4-propargyl-2-phenyl-Δ²-1,3,4-oxadiazolin-5-one 
• 21816-80-8 2-phenyl-4-ethyl-1,3,4-oxadiazol-5(4H)-one 
• 1199-02-6 5-phenyl-3H-[1,3,4]oxadiazol-2-one 
• 55084-87-2 2-phenyl-4-isobutyl-1,3,4-oxadiazol-5(4H)-one 

Relevant academic research and scientific papers

Synthesis and In Vitro Anticancer Activity of Novel 1,3,4-Oxadiazole-Linked 1,2,3-Triazole/Isoxazole Hybrids

A series of new 1,3,4-oxadiazole-linked 1,2,3-triazole/isoxazole derivatives were designed and synthesized. All the synthesized compounds were screened for in vitro anticancer activity against four human cancer cells: HeLa (cervical), MDA-MB-231 (breast), DU-145 (prostate), and HEPG2 (liver). Among 17 compounds tested, 7a, 7c, and 7d showed potent activity toward four cell lines.

Application of N-Acylbenzotriazoles in the Synthesis of 5-Substituted 2-Ethoxy-1,3,4-oxadiazoles as Building Blocks toward 3,5-Disubstituted 1,3,4-Oxadiazol-2(3H)-ones

5-Substituted-2-ethoxy-1,3,4-oxadiazoles were conveniently prepared through a one-pot sequential N-acylation/dehydrative cyclization between ethyl carbazate and N-acylbenzotriazoles in the presence of Ph3P-I2 as a dehydrating agent. Subsequent treatment with a stoichiometric amount of alkyl halides (X = Cl, Br, I) enables a rapid access to a variety of 3,5-disubstituted 1,3,4-oxadiazol-2(3H)-ones in good to excellent yields.

A convergent synthesis of 1,3,4-oxadiazoles from acyl hydrazides under semiaqueous conditions

The 1,3,4-oxadiazole is an aromatic heterocycle valued for its low-lipophilicity in drug development. Substituents at the 2- and/or 5-positions can modulate the heterocycle's electronic and hydrogen bond-accepting capability, while exploiting its use as a carbonyl bioisostere. A new approach to 1,3,4-oxadiazoles is described wherein α-bromo nitroalkanes are coupled to acyl hydrazides to deliver the 2,5-disubstituted oxadiazole directly, avoiding a 1,2-diacyl hydrazide intermediate. Access to new building blocks of oxadiazole-substituted secondary amines is improved by leveraging chiral α-bromo nitroalkane or amino acid hydrazide substrates. The non-dehydrative conditions for oxadiazole synthesis are particularly notable, in contrast to alternatives reliant on highly oxophilic reagents to effect cyclization of unsymmetrical 1,2-diacyl hydrazides. The mild conditions are punctuated by the straightforward removal of co-products by a standard aqueous wash.

Facile synthesis and stracture of novel 2,5-disubstituted 1,3,4-selenadiazoles

The reaction of hydrazide with carbony] chloride in the presence of sodium carbonates leads to the corresponding 1,2- diacylhydrazines [1a-t, R 1C(O)NHNHC(O)R2, R1 = aryl, R2 = aryl or alkyl] in moderate to excellent yield (57-90%). The latter reacts with 2,4-diphenyl-l,3-diselenadiphosphetane- 2,4-diselenide (Woollins' reagent, WR) in refluxing toluene to give a series of new 2,5-disubstituted 1,3,4-selenadiazoles (2a-t, 51-99% yield). All compounds were characterized spectroscopically and six compounds were characterized crystalloqraphically. Wiley-VCH Verlag GmbH & Co. KGaA.