Synthesis and Comparison of the Reactivity of 3,4,5‐1 H ‐Trinitropyrazole and Its  N ‐Methyl Derivative | Zendy

Dalinger Igor L. | Zendy; Vatsadze Irina A. | Zendy; Shkineva Tatyana K. | Zendy; Popova Galina P. | Zendy; Shevelev Svyatoslav A. | Zendy; Nelyubina Yuliya V. | Zendy

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Synthesis and Comparison of the Reactivity of 3,4,5‐1 H ‐Trinitropyrazole and Its N ‐Methyl Derivative

Author(s) -

Dalinger Igor L.,

Vatsadze Irina A.,

Shkineva Tatyana K.,

Popova Galina P.,

Shevelev Svyatoslav A.,

Nelyubina Yuliya V.

Publication year - 2013

Publication title -

journal of heterocyclic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.321

H-Index - 59

eISSN - 1943-5193

pISSN - 0022-152X

DOI - 10.1002/jhet.1026

Subject(s) - chemistry , nitration , nucleophile , phenols , reactivity (psychology) , medicinal chemistry , sulfuric acid , derivative (finance) , organic chemistry , nucleophilic substitution , nitro , ammonia , catalysis , medicine , alternative medicine , pathology , financial economics , economics , alkyl

3,4,5‐Trinitro‐1 H ‐pyrazole ( 1 ) has been obtained via nitration of 3,5‐dinitropyrazole with mixture of sulfuric and nitric acids. Compound 1 reacts with excess ammonia and aliphatic amines , in the presence of bases with NH‐azoles, phenols, thiols, and triflouroethanol at mild conditions in water. All these reactions occur as the nucleophilic substitution of the nitro‐group at position 4 in 1 affording 4‐R‐3,5‐dinitropyrazoles. The product of methylation of 1 , N ‐methyl‐3,4,5‐trinitropyrazole ( 4 ), also reacts with thiols, phenols, oximes, ammonia, amines, and NH‐azoles. The reactions proceed with high yields but nucleophilic substitutions in these cases occur regioselectively at position 5 in 4 to afford 5‐R‐3,4‐dinitropyrazoles.

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