1152-32-5

Usage

InChI:InChI=1/C14H13N3O2/c18-13(11-7-3-1-4-8-11)16-17-14(19)15-12-9-5-2-6-10-12/h1-10H,(H,16,18)(H2,15,17,19)

Upstream product

• 103-71-9 phenyl isocyanate 
• 613-94-5 benzoic acid hydrazide 
• 71-43-2 benzene 
• 109-95-5 ethyl nitrite 
• 64-17-5 ethanol 
• 67-64-1 acetone 
• 582-61-6 benzoyl azide 
• 1199-02-6 5-phenyl-3H-[1,3,4]oxadiazol-2-one 
• 62-53-3 aniline 

Downstream Products

• 2039-00-1 3,4-diphenyl-Δ²-1,2,4-triazolin-5-one 
• 124-38-9 carbon dioxide 
• 613-94-5 benzoic acid hydrazide 
• 62-53-3 aniline 
• 65-85-0 benzoic acid 
• 302-01-2 hydrazine 
• 65091-81-8 4,5-diphenyl-2-(2-propynyl)-2,4-dihydro-3H-1,2,4-triazol-3-one 
• 1351071-33-4 C₂₂H₂₂N₄O 
• 1351071-31-2 4,5-diphenyl-2-[4-(3-methylpiperidino)-2-butynyl]-2,4-dihydro-3H-1,2,4-triazol-3-one 
• 1351071-29-8 4,5-diphenyl-2-[4-(2-methylpiperidino)-2-butynyl]-2,4-dihydro-3H-1,2,4-triazol-3-one 
• 1351071-28-7 4,5-dipheny1-2-[4-(perhydroazocino)-2-butynyl]-2,4-dihydro-3H-1,2,4-triazol-3-one 
• 1351071-26-5 4,5-diphenyl-2-[4-(perhydroazepino)-2-butynyl]-2,4-dihydro-3H-1,2,4-triazol-3-one 
• 1351071-24-3 4,5-diphenyl-2-[4-(2,6-dimethylpiperidine)-2-butynyl]-2,4-dihydro-3H-1,2,4-triazol-3-one 
• 32380-24-8 N-(4-bromo-phenyl)-N-(5-phenyl-[1,3,4]oxadiazol-2-yl)-acetamide 

Relevant academic research and scientific papers

Synthesis, characterization and antioxidant activities of semicarbazide and thiosemicarbazide derivatives

In this research work Semicarbazide, thiosemicarbazide derivatives 3 to 25 were synthesized by conventional methods with high percentage yield and reaction rate. 1H-NMR and EIMS spectroscopic techniques were used to elucidate the structure of t

Oxadiazoles in medicinal chemistry

Oxadiazoles are five-membered heteroaromatic rings containing two carbons, two nitrogens, and one oxygen atom, and they exist in different regioisomeric forms. Oxadiazoles are frequently occurring motifs in druglike molecules, and they are often used with the intention of being bioisosteric replacements for ester and amide functionalities. The current study presents a systematic comparison of 1,2,4- and 1,3,4-oxadiazole matched pairs in the AstraZeneca compound collection. In virtually all cases, the 1,3,4-oxadiazole isomer shows an order of magnitude lower lipophilicity (log D), as compared to its isomeric partner. Significant differences are also observed with respect to metabolic stability, hERG inhibition, and aqueous solubil ity, favoring the 1,3,4-oxadiazole isomers. The difference in profile between the 1,2,4 and 1,3,4 regioisomers can be rationalized by their intrinsically different charge distributions (e.g., dipole moments). To facilitate the use of these heteroaromatic rings, novel synthetic routes for ready access of a broad spectrum of 1,3,4-oxadiazoles, under mild conditions, are described.

Synthesis and cyclisation of 1,4-disubstituted semicarbazides

Semicarbazides, besides possessing medicinal properties, also find wide applications in agriculture and industry. We report in this article the synthesis of the four 1,4-disubstituted semicarbazides: 1-cinnamoyl-4-phenyl semicarbazide (1), 1-oleyl-4-phenyl semicarbazides (2), 1,1',1''-tricitryl-4,4', 4''-triphenyl semicarbazide (3) and 1-benzoyl-4-phenyl semicarbazide (4), by the condensation of four different hydrazides: cinnamic acid hydrazide (5), oleic acid hydrazide (6), citric acid hydrazide (7) and benzoic acid hydrazide (8). The acid hydrazides were prepared by the condensation of four different acids with phenyl isocyanate. The semicarbazides were also subjected to acid catalysed intramolecular cyclisation. The cyclisation of (1) and (2) afforded substituted 1,3,4-oxadizoles: 2-cinnamoyl-5-aminophenyl 1,3,4-oxadizoles (9) and 2-oleyl-5-aminophenl 1,3,4-oxadizoles (10), respectively, in high yield, while no cyclisation occurred in the cases of (3) and (4). The products in each case have been identified on the basis of melting points and IR spectral studies.

The rapid preparation of 2-aminosulfonamide-1,3,4-oxadiazoles using polymer-supported reagents and microwave heating

Herein, we report on the preparation of a library of 5-substituted-2-amino- 1,3,4-oxadiazoles and the corresponding thiadiazole analogues. Presented is a one-pot preparation of the 2-aminosulfonylated analogues through a three component coupling of an acylhydrazine, an isocyanate and sulfonyl chloride promoted by a polymer-supported phosphazine base under microwave dielectric heating. Also described is the optimization process and details pertaining to the elucidation of the reaction products.

Ureylene anticonvulsants and related compounds

The results from a previous study led to the postulate that a number of aryl semicarbazones displaying anticonvulsant activity in the maximal electroshock (MES) screen interacted at both a hydrophobic and a hydrogen bonding areas on a specific binding site. These two parts of the binding site may be referred to as areas A and B, respectively. In order to circumvent the possible problems of the carbimino group in semicarbazones, such as toxicity and acid lability, some related ureylenes were considered. Initial evidence suggested that a second lipophilic group in the molecule was advantageous; this group may interact at area C on the proposed binding site. Most of the compounds prepared with a view to interacting at areas A, B and C showed protection in mice against MES induced siezures. Of particular interest were the compounds 1d, j which contained an α-methylbenzyl group attached to the N1 atom of the ureylenes which afforded good protection in the MES screen. The areas A and C at which lipophilic moieties were considered to interact were capable of accommodating groups of different sizes as measured by their solvent accessible surface areas. A number of compounds were active when given orally to rats and devoid of neurotoxicity at the doses utilized. Several compounds including 1d, f, j, 2d are useful prototypic molecules for subsequent development of further novel anticonvulsants.

An efficient synthesis of 1,3,4-oxadiazoles from N,N′-diacylhydrazines using Ph3P·Br2, Ph3P·CCl4 or Ph3P·CBr4 adducts as condensing agents

1,3,4-Oxadiazoles including 2-amino derivatives were effectively synthesized by treatment of N,N′-diacylhydrazines or N-acylsemicarbazides with Ph3P·Br2, Ph3P·CCl4 or Ph3P·CBr4 adducts in the presence of Et3N in CH2Cl2 under mild conditions.

Ring-Opening Reaction of 1,3,4-Oxadiazolone and 1,3,4-Oxadiazolinethione: Reaction of 2-Phenyl-1,3,4-oxadiazolin-5-one and 2-Phenyl-1,3,4-oxadiazoline-5-thione with Amines

The ring-opening abilities of amines toward 1,3,4-oxadiazolines, 2-phenyl-1,3,4-oxadiazolin-5-one (1a) and 2-phenyl-1,3,4-oxadiazoline-5-thione (1b), were investigated with relation to their basicities or pKb values.Oxadiazolines 1a and 1b were easily reacted with amines such as benzylamine and aniline, but not with p-nitroaniline, to form the corresponding ring-opening adducts.The reactions of both 1a and 1b with o-phenylenediamine produced benzodiazoles with the liberation of benzoylhydrazide, whereas the reactions with o-aminobenzamide furnished quinazolines with the liberation of ammonia. o-Aminophenol and o-aminothiophenol were also reacted with 1a and 1b both of them giving 1,5-dibenzoylcarbohydrazide from 1a and 1,2-dibenzoylhydrazine from 1b.From the conditions affording the corresponding ring-opening adducts or reaction products, the ring-opening abilities of the amines toward 1a and 1b are in good correlation with the strength of their basicities or pKb values.The ring-opening of oxadiazolines were proved to occur with anilines.Therefore, the other reactions are also supposed to proceed via the ring-opening steps.