Synthesis and synthetic applications of cyanoacetamides

Abstract

Approaches for the preparation of cyanoacetamide derivatives as well as the chemical reactivity profiles and structures of these substances are reviewed. The utility of these compounds as precursors is emphasized in the synthesis of five-and six-membered heterocycles and their fused heterocycles. The reported heterocyclic compounds in this review article are classified according to the kind of the heterocyclic systems.

The Aminometylation of 4-(Alkylthio)-6-amino-2-oxo(thioxo)-1,2-dihydropyridine-3,5-dicarbonitriles

“…Earlier we reported [4][5][6] the aminomethylation reaction of 6-amino-3,5,-dicyano-2-thioxo(oxo)-1,2-dihydropyridines leading to pyrido [1,2-a We prepared ketenedithioacetals 1 from carbon disulfide and malononitrile by known method [3]. Next, the reaction of the prepared ketendithioacetals 1 with active methylene compoundscyanoacetamide [7][8][9] or cyanothioacetamide [7,10] was performed. The reaction was carried out in i-PrOH in the presence of sodium isopropylate, followed by acidification with hydrochloric acid.…”

Synthesis of heterocyclic compounds via Michael and Hantzsch reactions

“…The reaction of 7‐aminopyrazolo[1,5‐ a ]pyrimidin‐5(4 H )‐one 113 with arylidenemalononitriles 45 in ethanol in the presence of piperidine as a catalyst afforded 4,5‐dihydropyrazolo[1,5‐ a ]pyrido[3,2‐ e ]pyrimidine‐7‐carbonitrile derivatives 114 in good yields (Scheme ) …”

Hantzsch-Like One-Pot Three-Component Synthesis of Heptaazadicyclopenta[a,j]anthracenes: A New Ring System

“…Attempts to isolate the cyanoacetamide intermediate 3 were unsuccessful. The structure of 5 was established by means of various spectroscopic techniques 25 and later confirmed by X-ray single-crystal structure analysis (Figure 1). It is clear that this compound can be considered as an enaminone that contains an amino group as a source of ammonia; we therefore investigated its utility in Hantzsch-like reaction.…”