ChemInform Abstract: Azolyl Derivatives of Nitrohalogenobutadienes. Part 2. Synthesis and Some Reactions of 1,1-Bis(3,5-dimethylpyrazol-1-yl) and 1,1-Bis(1,2,4-triazol-1-yl)-2-nitrotrihalogeno-1,3-butadienes.

✍ Scribed by V. A. ZAPOL'SKII; V. I. POTKIN; N. I. NECHAI; R. V. KABERDIN; M. S. PEVZNER

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 38 KB
• Volume: 29
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199834158

✦ Synopsis

Azolyl Derivatives of Nitrohalogenobutadienes. Part 2. Synthesis and Some Reactions of 1,1-Bis(3,5-dimethylpyrazol-1-yl) and 1,2,-Reaction of pentahalogenonitrobutadienes (I) with excess amounts of triazole or pyrazole (II) proceeds as electrophilic substitution of both the geminal chlorine atoms to afford the title diazolylbutadienes (III) as single structural isomers. These diazolylbutadienes (III) can undergo transamination with other primary or secondary amines to give the 1-azolyl-1-aminobutadienes (V) and (VII). The reaction of the dipyrazolylbutadienes (IIIa), (IIIb) with excess amounts of piperidine takes a different course to produce unexpectedly the 1,1-dipyrazolyl-4-piperidylbutadiene (VI) via nucleophilic vinyl substitution of the terminal halogen atom.

-(ZAPOL'SKII, V. A.; POTKIN, V. I.;