Synthesis of Some New Polyfunctionalized Pyridines

Abstract

in Wiley Online Library (wileyonlinelibrary.com).5-Methyl-2,4-dihydro-3H-pyrazol-3-one and/or 5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one was reacted with arylidenemalononitrile in the presence of sodium alkoxide to give 2-amino-6-alkoxy-4-arylpyridine-3,5-dicarbonitrile 4a-e instead of the reported pyrazolo[3,4-b]pyridine-5-carbonitriles. The same products 4a-e were prepared via reaction of arylidenemalononitrile with sodium alkoxide in an appropriative alcohol. However, the new synthetic route for preparation of their positional isomer 4-amino-6-alkoxy-2-arylpyridine-3,5-dicarbonitrile 7a-j has been achieved via reaction of 2-aminoprop-1-ene-1,1,3-tricarbonitrile with different aromatic aldehydes under the same conditions.

Catalyst-Solvent System for PASE Approach to Hydroxyquinolinone-Substituted Chromeno[2,3-b]pyridines Its Quantum Chemical Study and Investigation of Reaction Mechanism

“…During the NMR study, six major components were recorded: salicylaldehyde 1a, malononitrile dimer 2 and hydroxyquinolinone 3, intermediate 5, The starting materials are well known (we estimated the presence of salicylaldehyde 1a by the singlet at 10.25 ppm, malononitrile dimer 2 by the singlet at 3.85 ppm and hydroxyquinolinone by the singlet at 5.78 ppm); compound 4a is described in this manuscript and was estimated by the signal at 5.61 ppm; intermediate 5 was described previously (7.75 ppm) [40]; intermediate 7 was estimated by the signals at 8.04-8.11 ppm [41]. The starting materials are well known (we estimated the presence of salicylaldehyde 1a by the singlet at 10.25 ppm, malononitrile dimer 2 by the singlet at 3.85 ppm and hydroxyquinolinone by the singlet at 5.78 ppm); compound 4a is described in this manuscript and was estimated by the signal at 5.61 ppm; intermediate 5 was described previously (7.75 ppm) [40]; intermediate 7 was estimated by the signals at 8.04-8.11 ppm [41]. Based on these data and taking into consideration earlier published results [42,43], we suggest that the first stage was a rapid formation of intermediate 7 with expulsion of a hydroxide anion [37].…”

Untitled

“…X-ray diffraction data for complexes (I)-(IV) were collected at room temperature using graphite-monochromatic Mo Kα radiation (λ= 0.71073 Å) on an Oxford Diffraction GeminiS diffractometer. Structure solutions and refinements for complexes 1-2 were carried out with the programs SHELXT [20] and SHELXL-2018/3 [21], respectively. MERCURY [22] was employed for molecular graphics and OLEX2 [23].…”

One‐pot multicomponent designing of novel 2‐imino‐4‐arylidene‐1,3‐thiazolidin‐4‐one

“…3.2.5 | 3-cyclohexyl-2-(phenylimino)-1,3-thiazolidin-4-one (5) Yield 87% as a brown crystal, M.P: 90 C; IR: 3054 (CH aromatic ), 2932, 2854 (CH aliphatic ), 1711 (C O), 1626 (C N). 5H,CH 13 CNMR: 172.3,155.65,148.57,129.73,124.72,121.32,42.45,32.90,29.20,19.91,14. 3.2.7 | 3, 3 0 -Ethane-1,2-diylbis (2-phenylimino-1,3-thiazolidin-4-one) (7) Yield 89% as a yellow crystal, M.P: 90 C [reported 196-198 C] [32] ; IR: 3057 (CH aromatic ), 2977, 2945 (CH aliphatic ), 1730 (C O), 1622 (C N). 1 HNMR: 7.37-6.93 (m, 10H, CH arom.…”

“…[25] The multicomponent reactions (MCRs) are an efficient method in the field of heterocyclic synthesis because of their simplicity, high selectivity, reduced reaction time, good yielding, ego-friendly and easy workup. [26][27][28][29] This article is continuing of our previous works on the designing of new heterocyclic components [29][30][31][32][33][34] and due to the biological activities of 1,3-thiazolidin-4-one, this work goal for more investigation for synthesizing the new 2-imino-4-aryl-1,3-thiazolidin-4-ones through unpretentious one-pot three components involving the direct interacting between isothiocyanatobenzene, primary amines, and ethyl bromoacetate.…”