83326-53-8

Upstream product

• 916494-05-8 methyl 2-(4-chlorophenyl)-2-isocyanoacetate 
• 369-57-3 benzenediazonium tetrafluoroborate 
• 122-01-0 4-chloro-benzoyl chloride 
• 100-63-0 phenylhydrazine 
• 15089-07-3 2-(4-Chlorbenzoyl)-1-phenylhydrazid 
• 616-47-7 1-methyl-1H-imidazole 
• 36590-52-0 N-phenyl-p-chlorobenzohydrazonoyl chloride 
• 51112-85-7 4-chlorobenzonitrile N-phenylimine 
• 83326-46-9 2-(4-Chloro-phenyl)-6-imino-1-phenyl-1,6-dihydro-pyrimidine-5-carbonitrile 

Relevant academic research and scientific papers

Metal-free Decarboxylative Annulation of 2-Aryl-2-isocyano-acetates with Aryldiazonium Salts: General Access to 1,3-Diaryl-1,2,4-triazoles

Isocyanoacetates are versatile substrates for the synthesis of heterocyclic compounds, but the concomitant decarboxylation remains rare. Herein we report a decarboxylative annulation reaction of 2-aryl-2-isocyanoacetates with aryldiazonium salts. This metal-free, base-promoted protocol allows for the access to a broad collection of 1,3-diaryl-1,2,4-triazoles, including chiral triazole-based binaphthalene ligands, drug mimics, and synthetic intermediates of druglike molecules. (Figure presented.).

A formal [3+2] cycloaddition reaction of: N -methylimidazole as a masked hydrogen cyanide: Access to 1,3-disubstitued-1 H -1,2,4-triazoles

N-Methylimidazole (NMI) can act as a masked HCN in the synthesis of 1,3-disubstitued-1H-1,2,4-triazoles via a formal cycloaddition reaction of hydrazonoyl chloride with NMI. The product was proved to be formed via an initial nucleophilic substitution of hydrazonoyl chloride with NMI following cyclization and two sequential C-N bond cleavages. This journal is

REACTIVITE DE LA N-ETHOXYCARBONYL-N-(2,2,2-TRICHLOROETHYLIDENE)AMINE AVEC LES PRECURSEURS DE QUELQUES DIARYLNITRILIMINES ET QUELQUES ARYLNITRILOXYDES

The reaction of diarylnitrilimines 2 with N-ethoxycarbonyl-N-(2,2,2-trichloroethylidene)amine 1 gives substituted 1,2,4-triazolines 4.With the arylnitriloxides precursors 3, the cycloaddition reaction competes with a nucleophilic addition leading to a mixture of substituted 1,2,4-oxadiazoline 6 and ethyl 1-O-(α-chloroaraldoximino)-2,2,2-trichloroethylcarbamate 7.

SYNTHESIS OF TRIAZOLES AND OXADIAZOLES FROM 2-ARYL-3-PHENYL-4-IMINO-5-CYANO-3,4-DIHYDROPYRIMIDINES

2-Aryl-3-phenyl-4-imino-5-cyano-3,4-dihydropyrimidines I were transformed to 1,2,4-triazoles II,IV and 1,2,4-oxadiazoles III by treatment with hydrazine, arylhydrazines or hydroxylamine in yields up to 90percent.