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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.