139347-62-9Relevant academic research and scientific papers
Factors Affecting Rates of Thermal Decomposition of 5-Azidopyrazoles: A Comparison with other Aromatic Azides
L'abbe, Gerrit,Dyall, Leonard,Meersman, Kathleen,Dehaen, Wim
, p. 2401 - 2406 (2007/10/02)
2-Methoxyazidobenzene has been used as a model compound for α-azido five-membered heterocycles, and undergoes thermal loss of nitrogen 16 times as fast as azidobenzene and 3.6 times as fast as its para isomer.These rates identify an important electrostati
Azide Ring-Opening-Ring-Closure Reactions and Tele-substitutions in Vicinal Azidopyrazole-, Pyrrole- and Indolecarboxaldehydes
Becher, Jan,Joergensen, Per Lauge,Pluta, Krystian,Krake, Niels J.,Faelt-Hansen, Birgitte
, p. 2127 - 2134 (2007/10/02)
5-Chloro-1-methylpyrazole-4-carboxaldehydes 1 react with excess sodium azide in dimethyl sulfoxide to produce a mixture of 1-azidomethyl-4-cyanopyrazoles 2 and 4-cyano-5-hydroxy-1-methylpyrazoles 3.Application of this reaction to the corresponding 5-chloro-1-phenylpyrazole-4-carboxaldehydes 5 gave 4-cyano-5-hydroxy-1-phenyl-pyrazoles 7 as the sole products in high yields.Likewise, 2-aryl-5-chloro-1-methylpyrrole-3,4-dicarboxaldehydes 9 rearranged to 2-aryl-4-cyano-5-hydroxy-1-methylpyrrole-3-carboxaldehydes 10 in high yields.In the indole series, treatment of 1-aryl-2-chloroindole-3-carboxaldehydes 11 with NaN3 yielded a mixture of 1-aryl-3-cyano-2(3H)-indolones 13 and 1-aryl-5-azido-3-cyanoindoles 12, both products resulting from a ring-opening-ring-closure reaction with concomitant nucleophilic tele-substitution at the 5-position of the indole ring.
