ChemInform Abstract: Potential Cardiotonic Agents. Part 4. Synthesis, Cardiovascular Activity, Molecular, and Crystal Structure of 5‐Phenyl‐ and 5‐(4‐Pyridinyl)‐Substituted 2(1H)‐Pyridinethiones.

Abstract

ChemInform Abstract The butenones (I) are cyclized with cyanothioacetamide (II) to form the pyridinethiones (III). Especially derivative (IIIa) exhibits positive inotropic potency and vasodilatoric activity. (X-Ray data of (IIIa)).

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

“…86, 87, 468 ± 472 3-Cyano-5-aryl-6-methylpy-ridine-2(1H)-thiones 189 (X = S) were synthesised in a similar way from the enamino ketone 190 [R 1 7R 2 = (CH 2 ) 2 O(CH 2 ) 2 ]. 473 The well-known cardiotonic preparation `milrinone' (192) is obtained by the condensation of the enamine 191 with cyanoacetamide (1a) or malononitrile (5). 474 The reaction of enamine 193 with the amide 1a in isopropyl alcohol in the presence of sodium alkoxides is nonselective and results in a mixture of pyridones 194 and 195.…”