V-TRIAZOLINES - 39 - 1,2,4-TRIARYL-3-AMINOPYRROLES - UNUSUAL REACTION-PRODUCTS IN THE PYROLYSIS OF 5-AMINO-V-TRIAZOLINES AND THE CRYSTAL-STRUCTURE OF 2-(3-MORPHOLIN-4-YL-2,4-PYRROL-1-YL)BENZONITRILE
D. Pocar et al., V-TRIAZOLINES - 39 - 1,2,4-TRIARYL-3-AMINOPYRROLES - UNUSUAL REACTION-PRODUCTS IN THE PYROLYSIS OF 5-AMINO-V-TRIAZOLINES AND THE CRYSTAL-STRUCTURE OF 2-(3-MORPHOLIN-4-YL-2,4-PYRROL-1-YL)BENZONITRILE, Journal of heterocyclic chemistry, 35(3), 1998, pp. 687-692
Pyrolysis of 4-aryl-5-amino-v-triazolines affords, generally, amidines
and/or benzanilides. Pyrolysis of 4-aryl-5-morpholino-v-triazolines 6
, together with the expected amidines 7 and/or aryanilides 8, produced
the morpholinopyrroles 9. The reaction mechanism of this unusual tran
sformation is discussed. Influence of solvent dipole moment in pyrrole
formation is suggested. Pyrrole 9a [i.e. 2-(3-morpholin-4-yl-2,4-pyrr
ol-1-yl)benzonitrile] has been fully characterized and its molecular s
tructure has been determined by X-ray diffraction analysis.