ChemInform Abstract: Cyclization Reactions of Nitriles. Part 17. Synthesis and Mass Spectrometric Investigation of 4,6‐Diaryl‐3‐cyano‐2(1H)pyridinethiones.

Abstract

Beschreibungen von Synthesen der vielseitig verwendbaren Titelverbindungen (II) finden sich in der Literatur nur vereinzelt.

Reactions of carbonyl compounds with α,β-unsaturated nitriles as a convenient pathway to carbo- and heterocycles

“…Study of the regularities of recyclisation made it possible to offer a convenient method for the synthesis of substituted pyridinethiones 327. 46,200,201 This method consists in interaction of arylidenecyanothioacetamides 52 with a broad range of carbonyl compounds such as aliphatic ketones, 35,46,201,202 substituted acetophenones, 202,203 and cyclic ketones, 35,46,200,201 and also enamines. Due to the high reactivity of enamines, it is better to use them in this reaction.…”

Multicomponent Reactions of Carbonyl Compounds and Derivatives of Cyanoacetic Acid: Synthesis of Carbo- and Heterocycles

“…To some extent, the proposed reaction scheme was confirmed by introducing Michael adducts into this synthesis; these Michael adducts had previously been used as starting reagents for the preparation of pyridine-2(1H)-thiones 194. [147][148][149] In addition, pyridine-2(1H)-thiones were synthesized from a-bromoketonitriles and sodium hydrosulfide through the corresponding amercaptoketonitriles 192. 149 A multicomponent reaction of aldehydes, cyanothioacetamide, and 1,3-dicarbonyl compounds has found wideranging application in the synthesis of hydrogenated pyridine-2(1H)-thiones.…”

Cyanoacetamides and their thio- and selenocarbonyl analogues as promising reagents for fine organic synthesis

“…28, 85, 337 ± 352 Similar reaction of monothiodibenzoylmethane (130) with cyanothioacetamide (1b) in ethanol in the presence of piperidine gives rise to 3-cyano-4,6-diphenylpyridine-2(1H)-thione. 353 It is noteworthy that pyridin-2(1H)-ones 129a were obtained by the above method as far back as the end of the past century, while the first thione analogue, viz., 3-cyano-4,6-dimethylpyridine-2(1H)-thione, was synthesised by condensation of acetylacetone with the amide 1b at the end of the 1950's, 338,341 and the first selenone analogue was prepared in a similar way from the amide 1c only in 1985. 47 Reactions of cyanothioacetamide (1b) occur under milder conditions and give higher yields of pyridines than with cyanoacetamide (1a).…”