Synthesis of novel 4-acyl-2-amino-6-sulfanylpyridine-3,5-dicarbonitriles

2-Amino-3,5-dicarbonitrile-6-sulfanylpyridines: synthesis and multiple biological activity – a review

“…Grigor'ev and co-workers 91 developed an original approach for the synthesis of privileged scaffolds, 4-acyl-2-amino-3,5-dicarbonitrile-6-sulfanylpyridines 14, by heterocyclization of potassium 2-acyl-1,1,3,3-tetracyanopropenides 13 with thiols 2 in superbasic medium, DMSO-Na or DMSO-NaH, 92 in which the target products were formed in more than 60% yields ( Scheme 6 ).…”

Synthesis and Solid State Fluorescence of Malononitrile Trimer Ylidene Derivatives in Aqueous Medium under Ultrasonication

“…IR spectrum, ν, cm -1 : 2194 (C≡N), 1583 (C=C). 1 H NMR spectrum, δ, ppm: 3.85 s (3H, OCH 3 ), 7.14 d (2H, C 6 H 4 , J = 8.9 Hz), 7.73 s (1H, CH), 7.93 d (2H, C 6 H 4 , J = 8.9 Hz). 13…”

“…Compounds containing a 1,1,3,3-tetracyano propenide fragment have attracted much interest due to their great potential for the synthesis of five-and sixmembered heterocycles, including fused ones [1][2][3][4][5], as well as their thermo-and photochromic [6], semiconducting [7], magnetic [6,8], and chemosensory properties [9]. We previously reported the synthesis of potassium (Z)-4-aryl-2-(dicyanomethylidene)-1,1,3-tricyanobut-3-en-1-ides 1 and (3Z,5E)-6-aryl-2-(dicyanomethylidene)-1,1,3-tricyanohexa-3,5-dien-1-ides 2 by Knoevenagel condensation of substituted benzaldehydes [9] and cinnamaldehydes [10] with malononitrile trimer potassium salt 3 in propan-2-ol or in aqueous medium in the presence of surfactants, e.g., Oksipav AP [11].…”

“…Yield 79%, mp 216-217°C (decomp.). IR spectrum, ν, cm -1 : 2195 (C≡N), 1583 (C=C) 1. H NMR spectrum, δ, ppm: 3.88 s (3H, OCH 3 ), 7.12 t (1H, C 6 H 4 , J = 7.6 Hz),…”

A new route to highly substituted thieno[2,3-b]pyridines via cascade heterocyclization of 2-acyl-1,1,3,3-tetracyanopropenide salts

“…14 Using of weaker bases leads to low yields. 15 The method is limited to aromatic and heteroaromatic acyl groups, ATCN with aliphatic acyl groups produce dihydrofuran derivatives. 16 A proposed mechanism for this reaction involves nucleophilic addition of thiol to ATCN cyano group and subsequent Thorpe-Ziegler cyclization of the intermediate pyridine B.…”