Unusual Reactions of 4,6‐Dichloro‐5‐nitropyrimidine with C‐Nucleophiles.

Abstract

Interaction of title compound (I) with pyrazolone (II) yields the dipyrazolylmethane (III) as major product besides the two-halogen replacement product (IV). The unusually easy reaction of (I) with indole (V) is explained by evolving hydrogen chloride, which catalyzes indole addition and disintegration of the intermediate yielding salt (VI). The tris(indolyl)methane (VII) results from addition of the third methylindole molecule to diindolylmethane (VI). Replacement of one indolyl moiety occurs in the reaction course of salt (VI) with dimethylbarbituric acid (VIII). The latter compound reacts with dimethylsulfoxide (X) to betaine (XI) in the presence of (I) as dehydrating reagent.-(AZEV*, Y. A.; DUELCKS, T.; LORK, E.; GABEL, D.; Mendeleev Commun. 2005, 5, 193-196; Ural State Tech. Univ., Ekaterinburg 620002, Russia; Eng.) -H. Hoennerscheid 03-043

Specific features of the interaction of fervenulin and its 4-N-oxide with C-nucleophiles: Structural and spectroscopic characteristics of molecular complexes and covalent adducts with indoles

“…The XRD data for the crystals of fervenulin (IV) and its 4-N-oxide (Ia) were reported elsewhere [13,14].…”