Nitriles in Heterocyclic Synthesis: The Reaction of 2-Thiocarbamoyl Cinnamonitriles with Active Methylene Reagents

Abstract

<jats:title>Abstract</jats:title><jats:p> Substituted pyridin-2-thiones, 2-pyridones, thiopyrans and pyranoazoles could be synthesized via the reaction of 2-thiocarbamoyl cinnamonitriles with some active methylene reagents.</jats:p>

Reactions with 3,6‐Diaminothieno[2,3‐b]pyridines: Synthesis and Characterization of Several New Fused Pyridine Heterocycles.

“…It has been found that 6-amino-4-(4methoxyphenyl)-2-thioxo-1,2-dihydropyridine-3,5dicarbonitrile (1) [25] reacted with chloroacetonitrile (2a) in cold DMF in the presence of potassium hydroxide to give a reaction product resulting from equimolecular addition of the reagent to the reactant with the loss of one molecule of hydrogen chloride. The IR spectrum of this reaction product showed among its absorption bands those corresponding to the presence of one NH 2 (3380, 3327 cm −1 ) and CN (2252, 2211 cm −1 ) functions.…”

“…Compounds 1 [25] were prepared according to the literature procedures. Compounds 1 [25] were prepared according to the literature procedures.…”

“…Center of Cairo University. Compounds 1 [25] were prepared according to the literature procedures. In all the 1 H NMR spectra * = Lost after D 2 O exchange.…”

Reactions with Dimethylformamide‐Dimethylacetal: Synthesis and Reactions of Several New Pyridine and Pyrazolo[3,4‐b]pyridine Derivatives.

“…It has been found that 6-amino-4-(4methoxyphenyl)-2-thioxo-1,2-dihydropyridine-3,5-dicarbonitrile (1a) [21] reacted with dimethylformamide-dimethylacetal (DMF-DMA) in dry xylene to afford a reaction product of molecular formula C 17 H 15 N 5 OS corresponding to equimolecular addition of 1a to the reagent followed by loss of two molecules of methanol. The IR spectrum of this reaction product showed the absence of the band of the amino group.…”

Reactions with dimethylformamide‐dimethylacetal: Synthesis and reactions of several new pyridine and pyrazolo[3,4‐b]pyridine derivatives

“…Elemental analyses were carried out at the Microanalytical Center of Cairo University. Compounds 1a [21] and 1b [22] were prepared according to the literature procedures.…”