65785-05-9

Upstream product

• 81823-70-3 4-(L-threo-2,3-dibenzoyloxy-1-hydroxypropyl)-2-phenyl-1,2,3-triazole-5-carboxylic acid 5,1¹-lactone 
• 65785-03-7 L-threo-2,3-hexodiulosono-1,4-lactone 3-oxime 2-(phenylhydrazone) 
• 28912-21-2 L-threo-2,3-hexodiulosono-1,4-lactone 2-(phenylhydrazone) 
• 69401-28-1 2-(phenyl)-4-(2,3-di-O-acetyl-D-erytro-glycerrol-1-yl)-1,2,3-triazole-5-carboxylic acid 5,1¹-lactone 
• 69346-96-9 D-erythro-2,3-hexodiulosono-1,4-lactone 2-(phenylhydrazone) 3-oxime 
• 28912-21-2 D-erythro-2,3-hexodiulosono-1,4-lactone 2-(phenylhydrazone) 
• 100-63-0 phenylhydrazine 
• 5959-82-0 D-erythro-2,3-hexodiulosono-1,4-lactone 

Downstream Products

• 65785-06-0 2-phenyl-4-(1,2,3-tri-O-acetyl-D-erythro-glycerol-1-yl)-1,2,3-triazole-5-carboxamide 
• 81823-71-4 2-phenyl-4-(L-threo-1,2,3-tribenzoyloxypropyl)-1,2,3-triazole-5-carboxamide 

Relevant academic research and scientific papers

STUDIES ON DEHYDRO-D-arabino-ASCORBIC ACID 2-ARYLHYDRAZONE 3-OXIMES: CONVERSION INTO SUBSTITUTED TRIAZOLES AND ISOXAZOLINES

D-erythro-2,3-Hexodiulosono-1,4-lactone 2-arylhydrazones (2) were prepared by condensation of dehydro-D-arabino-ascorbic acid with the desired arylhydrazine.Reaction of 2 with hydroxylamine gave the 2-arylhydrazone 3-oximes (3).On boiling with acetic anhy

STUDIES ON DEHYDRO-L-ASCORBIC ACID 3-OXIME 2-PHENYLHYDRAZONE: CONVERSION INTO SUBSTITUTED TRIAZOLES

L-threo-2,3-Hexodiulosono-1,4-lactone 3-oxime 2-(phenylhydrazone) (1) gave 2-(p-bromophenyl)-4-(L-threo-1,2,3-trihydroxypropyl)-1,2,3-triazole-5-carboxylic acid 5,11-lactone (2), and this gave a diacetyl and a dibenzoyl derivative.On treatment of 2 with liquid ammonia, methylamine, or dimethylamine, the corresponding triazole-5-carboxamides (5-7) were obtained.Periodate oxidation of 5 gave 2-(p-bromophenyl)-4-formyl-1,2,3-triazole-5-carboxamide (10),and, on reduction, 10 gave 2-(p-bromopheyl)-4-(hydroxymethyl)-1,2,3-triazole-5-carboxamide, characterized as its monoacetate.Condensation of 10 with phenylhydrazine gave the triazole hydrazone.Acetonation of 2 gave the isopropylidene derivative.Reaction of 2 with HBr-HOAc gave 4-(L-threo-2-O-acetyl-3-bromo-1,2-dihydroxypropyl)-2-(p-bromophenyl)-1,2,3-triazole-5-carboxylic acid 5,11-lactone.Similar treatment of 1 with HBr-HOAc gave 5-O-acetyl-6-bromo-6-deoxy-L-threo-2,3-hexodiulosono-1,4-lactone 3-oxime 2-(phenylhydrazone).This was converted into 4-(L-threo-2-O-acetyl-3-bromo-1,2-dihydroxypropyl)-2-phenyl-1,2,3-triazole-5-carboxylic acid 5,11-lactone on treatment with boiling acetic anhydride.On reaction of 1 with benzoyl chloride in pyridine, dehydrative cyclization occurred, with the formation of 4-(L-threo-2,3-dibenzoyloxy-1-hydroxypropyl)-2-phenyl-1,2,3-triazole-5-carboxylic acid 5,11-lactone, which was converted into the amide on treatment with ammonia.