180779-87-7

Upstream product

• 762-42-5 dimethyl acetylenedicarboxylate 
• 199450-68-5 2-(4-Bromo-phenyl)-3-methyl-4,5-diphenyl-3,4-dihydro-2H-[1,2,3]triazole-4-carbonitrile 
• 18411-25-1 2-(4-bromophenyl)-4,5-diphenyl-2H-1,2,3-triazole 

Downstream Products

• 100-47-0 benzonitrile 

Relevant academic research and scientific papers

Ring expansions of N-methyl-1,2,5-oxadiazolium and 1,2,3-triazolium perchlorate salts with bases to six-membered azines: Direct detection of an addition intermediate in an addition-elimination mechanism and a degradation of 1,2,5-oxadiazolium salts to aα-cyano nitrones

Reactions of 2-methyl-1,2,5-oxadiazolium perchlorate salts and 1-methyl-2-aryl-1,2,3-triazolium perchlorate salts with the bases KCN, NaOEt, KOBuf, LiNPrl2 give ring expansions to substituted 1,2,5-oxadiazines and 1,2,4-triazines. With cyanide as base the reactions follow an addition-elimination pathway and in two cases the addition intermediate has been isolated or directly detected by low-temperature NMR spectroscopy. The oxadiazolium system with cyanide also gives a useful new route to α-cyano nitrones via a ring degradation which competes with ring expansion. The reactions with KOBut and LiNPri2 do not involve an addition of the base to the azolium salt. Reactions have been monitored by 13C NMR spectroscopy by using 13CN-. An X-ray crystal structure is reported for (E)-N-(α-cyanobenzylidene)methylamine N-oxide.

1,2,3-Triazolium-1-unsubstituted methanides, carbon analogues of triazole-N-oxides: A 1,3-dipole cascade from 1,2,3-triazolium-1-methanide to 1,2,4-triazinium-4-methanide: New routes to pyrrolo[1,2-c] [1,2,3]triazoles, pyrrolo[1,2-d] [1,2,4]triazines and substituted 1-aminopyrroles. Azolium 1,3-dipoles

A 1,2,3-triazolium-1-methanide species has been generated and trapped in cycloadditions with alkyne dipolarophiles. The triazolium-1-methanide, a direct carbon analogue of the triazole-N-oxide, is an unstable intermediate prone to ring-opening and re-cyclisation to a 1,2,4-triazine system. New routes to substituted pyrrolo[1,2-c][1,2,3]triazoles, pyrrolo[1,2-d][1,2,4]triazines and substituted 1-aminopyrroles have resulted from this work. X-Ray crystal structures are described for 1,3,3a-triphenyl-4,5-diethoxycarbonyl-3a,6-dihydropyrrolo[1,2-c][1,2,3]triazole 6a, 1-N-anilino-2-phenyl-3,4-diethoxycarbonylpyrrole 9a and 3-(p-methoxyphenyl)-1,8a-diphenyl-8-exo-ethoxycarbonyl-3,4,6,7,8,8a- hexahydropyrrolo [1,2-d][1,2,4] triazine 15d.

Generation and trapping of a 1,2,3-Triazolium Methanide. A Carbon Analogue of the Azole N-Oxide: Routes to Pyrrolotriazoles and Substituted 1-Aminopyrroles

Trapping of the first azole N-unsubstituted methanide species, a carbon analogue of the ubiquitous azole N-oxide system is described; new synthetic routes to pyrrolotriazoles and 1-aminopyrroles have resulted.