- Structure of cyanoacetylhydrazones of aldehydes and ketones
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1D 1H and 13C, and 2D 1H NOESY NMR were used to establish that cyanoacetylhydrazones of aliphatic and aromatic aldehydes and ketones in CDCl3 and (CD3)2SO solutions have a linear structure,
- Zelenin,Oleinik,Alekseev,Potekhin
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- 7-Amino-2-aryl/hetero-aryl-5-oxo-5,8-dihydro[1,2,4]triazolo[1,5-a]pyridine-6-carbonitriles: Synthesis and adenosine receptor binding studies
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A series of novel 7-amino-5-oxo-2-substituted-aryl/hetero-aryl-5,8-dihydro[1,2,4]triazolo[1,5-a]pyridine-6-carbonitriles (4a–4t) was synthesized, characterized and evaluated for their binding affinity and selectivity towards hA1, hA2A/sub
- Shaik, Khasim,Deb, Pran Kishore,Mailavaram, Raghu Prasad,Chandrasekaran, Balakumar,Kachler, Sonja,Klotz, Karl-Norbert,Jaber, Abdul Muttaleb Yousef
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p. 1568 - 1573
(2019/05/27)
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- N-Substituted cyanacetohydrazides in the synthesis of 3,3-dialkyl-1,2,3,4-tetrahydroisoquinolines by Ritter reaction
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[Figure not available: see fulltext.] Cyanacetohydrazide, protected at the nitrogen atom of hydrazide group, underwent cyclocondensation by Ritter reaction with 3,3-dialkylbenzylcarbinols, forming 3,3-dialkyl-1,2,3,4-tetrahydroisoquinolines. The reagents
- Mikhailovskii, Alexander G.,Korchagin, Denis V.,Yusov, Aleksey S.,Gashkova, Oksana V.
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p. 1114 - 1119
(2017/12/08)
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- Synthesis, anti-hepatitis B and C virus activity and antitumor screening of novel thiazolo[4,5-D]-pyrimidine derivatives
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The paper describes the synthesis, antivirus and antitumor evaluation of novel thiazolo[4,5-d]pyrimidine derivatives. The target compounds 3a-h were synthesized by cyclocondensation of 4-amino-Ni-(phenylmethylidene)- 3-phenyl-2-thioxo-2,3-dihydrothiazole-
- Becan, Lilianna,Wójcicka, Anna
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p. 107 - 114
(2016/03/19)
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- Microwave assisted synthesis and evaluation of N-cinnamoyl aryl hydrazones for cytotoxic and antioxidant activities
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A series of N-cinnamoyl aryl hydrazones 2a-2i were synthesized in good yields by microwave irradiation technique. The title compounds were formed by nucleophilic condensation of various N1- substituted benzylidene-2-cyano aceto hydrazides with
- Devi, T. Sarala,Rajitha
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p. 1703 - 1709
(2016/08/06)
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- Ionic liquid and Lewis acid combination in the synthesis of novel (E)-1-(benzylideneamino)-3-cyano-6-(trifluoromethyl)-1H-2-pyridones
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In this work, a new catalytic system to synthesize a series of new (E)-1-(benzylideneamino)-3-cyano-6-(trifluoromethyl)-1H-2-pyridones from the cyclo-condensation reaction of benzylidene cyanoacetohydrazide with 4-alkoxy-1,1,1-trifluoro-3-alken-2-ones [CF3C(O)C (R2) = C(R1)(OR), where R = Me, Et; R1 = H, Me, Pr, Bu, Ph, 4-Me-Ph, 4-F-Ph, 4-Cl-Ph, 4-Br-Ph; R2 = H, Me and R 1,R2 = -(CH2)4-] is presented. The products were obtained at room temperature in moderate to good yields (42-87%). Comparison of the catalytic system with a conventional method was not possible, because the products were obtained only when the new catalyst system - consisting of triethylamine and Lewis acid in ionic liquid [BMIM][BF 4] - was used. Springer-Verlag 2011.
- Moreira, Dayse N.,Frizzo, Clarissa P.,Longhi, Kelvis,Soares, Aline B.,Marzari, Mara R.B.,Buriol, Lilian,Brondani, Sergio,Zanatta, Nilo,Bonacorso, Helio G.,Martins, Marcos A.P.
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p. 1265 - 1270
(2012/06/04)
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- Facile route for the synthesis of pyridazine derivatives: Unexpected pathway to benzothiazole, benzimidazole, and triazole derivatives
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4-Amino-5-arylmethylidene-3-phenyl-pyridazin-6-ones 7 have been synthesized and reacted with selected nucleophile reagents such as phenyl hydrazine, semicarbazide, semithiocarbazide, cyanoacetohydrazide, 2-aminothiophenol, and 2-phenylenediamine in ethanol triethyl-amine solution. An unexpected 1-phenyl-3-arylaziridene 10, 3-aryl-5-oxo(thio)-1,2,4-triazole 21, 4-amino-3-aryl-6-hydroxy-pridazine 27, 2-arylbenzothiazole 30a-c, and 2-arylbenzimidazole 30d-f have been obtained, respectively. Also, 2-aminothiophenol and 2-phenylenediamine were reacted with N-phenylmethylidene- 2-cyanoacetohydrazide 2, affording the new 1,4-benzodiazepine derivatives 35. Copyright Taylor & Francis LLC.
- El Rady, Eman A.
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- Studies with Polyfunctionally Substituted Heteroaromatics: A Route for the Synthesis of Substituted [1,2,4]Triazolo[1,5-a]pyridines
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N-Arylmethylidene-2-cyanoacetohydrazides react with arylmethylidenemalonitriles to afford [1,2,4]triazolo[1,5-a]pyridinones, and with both malononitrile and ethyl cyanoacetate to afford N-aminopyridinones.
- Al-Najjar, Abdul Aziz A.,Amer, Samier Abdul Rahman,Riad, Mohamed,Elghamry, Ibrahim,Elnagdi, Mohamed Hilmy
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p. 296 - 297
(2007/10/03)
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- Pyrolysis of amino nitriles, cyanohydrazones, and cyanoacetamides. Part I. Elimination reaction of 1-arylmethyleneamino-1,2-dihydro-4, 6-dimethyl-2-oxopyridine-3-carbonitriles and substituted benzaldehyde cyanoacetylhydrazones
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Pyrolysis of the Schiff bases of 1-arylmethyleneamino-1,2-dihydro-4, 6-dimethyl-2-oxopyridine-3-carbonitriles (1-5) has been studied. These compounds eliminate via a six-membered transition state to produce substituted benzonitriles and 2-hydroxy-4,6-dimethylpyridine-3-carbonitrile. These eliminations are unimolecular first-order reactions. The kinetic data gave a good correlation with σ0 values of the substituents on the aryl group with ρ = 0.83 at 520 K. Utilization of the pyrolytic reaction in synthesis of various benzonitriles is considered, and mechanistic information has been obtained by comparing the kinetic data and product analysis of the Schiff bases with their open-chain substituted benzaldehyde cyanoacetylhydrazones (6-9) analogues.
- Al-Awadi,Elnagdi,Mathew,El-Gamry,Abdel Khalik
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p. 741 - 748
(2007/10/03)
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- The Complex Reaction of Acetohydrazides with Unsaturated Diketones: Alternative Cyclizations to 1,2-Diazepin-3-ones and Pyrazolopyridines
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The reaction of 2-cyanoacetohydrazide (1) and 2-(ethoxycarbonyl)acetohydrazide (26) with unsaturated 1,3-diketones leading with moderate yields to 1,2-diazepinones (3, 23, 24) and pyrazolopyridines (5, 15, 20, 25) together with the corresponding acetohydrazones have been studied.The reaction course depends on the temperature and the relative reactivity of the carbonyl groups of the starting materials.When one of these carbonyl groups is less reactive (benzoyl or ethoxycarbonyl groups), the reaction does not yield diazepinones but only pyrazolopyridines and/or acetohydrazones.
- Alonso, Paloma,Martin-Leon, Nazario,Quinteiro, Margarita,Seoane, Carlos,Soto, Jose L.
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p. 841 - 846
(2007/10/02)
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- A Novel Example of a 7-exo-trig Heterocyclization
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We report that the open-chain hydrazide 12, resulting from Knoevenagel condensation of cyanoacetohydrazide (10) with 3-benzylidene-2,4-pentanedione (11), undergoes a 7-exo-trig heterocyclization, leading to the 1,3-diazepinone 14.
- Martin, Nazario,Quinteiro, Margarita,Seoane, Carlos,Soto, Jose L.
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p. 1051 - 1053
(2007/10/02)
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- Nitriles in Heterocyclic Synthesis: New Approaches for Synthesis of Some Pyridine Derivatives
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A variety of pyridines was prepared from reaction of N-benzylidenecyanoethanoic hydrazide (2) with malononitrile, benzoylacetonitrile, cyanoacetamide and cinnamonitrile derivatives.The reactivity of 2 towards a variety of ketones was studied. - Keywords:
- Ibrahim, N. S.,Mohareb, R. M.,Shams, H. Z.
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p. 1351 - 1354
(2007/10/02)
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- Reaction of α-Cyano-β-aryl Acrylic Acid Ethylesters with Hydrazine, a Retro-Knoevenagel-Reaction
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We tried to obtain 4-cyano 5-aryl pyrazolidones-(3) 3a, b and related azomethine imines 4a, b.However the reaction of α-cyano β-aryl acrylic acid ethylesters 2a, b with hydrazine yields the familiar cyano acetic acid arylidene hydrazides 5a, b by cleavage
- Geissler, G.,Hippius, M.,Tomaschewski, G.
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p. 910 - 914
(2007/10/02)
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