- Chitosan based heterogeneous catalyses: Chitosan-grafted-poly(4- Vinylpyridne) as an efficient catalyst for michael additions and alkylpyridazinyl carbonitrile oxidation
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Chitosan-grafted-poly(4-vinylpyridine) (Cs-PVP) copolymers could be synthesized under heterogeneous conditions in presence of a potassium persulfate and sodium sulfite redox system. The synthesized graft copolymer could be utilized effectively, in the form of beads, as an efficient catalyst for Michael additions of active methylenes to functionally substituted alkenes. Moreover, methyl moiety oxidation in methyl pyridazinyl carbonitriles by H 2O2 in the presence of chitosan-g-polyvinyl pyridine-supported iron (III) complex, Cs-PVP/Fe, could be affected. A variety of pyrans, naphthopyrans, and thiopyrans could be synthesized efficiently in the presence of these graft copolymer beads by novel catalytic routes. These polymeric catalysts could be used instead of the old toxic commercial organic basic catalysts, piperidine or pyridine, and could be readily isolated from the reaction mixture and recycled several times without significant loss of catalytic activity.
- Khalil, Khaled D.,Al-Matar, Hamad M.
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- Mechanistic study on a novel pseudo-five-component synthesis of 4H-thiopyrans
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The use of carbon disulfide provides a novel and efficient route for the synthesis of thiopyrans. Herein we describe a study on the pseudo-five-component preparation of 4H-thiopyran derivatives by condensation of aldehydes, malononitrile, carbon disulfide, and primary amines in the presence of triethylamine. Separation and identification of the reaction intermediates and products, additional starting materials designing, repeating of the reaction, and determining of the products, NMR, and GC-mass analysis of the reaction mixtures, were used to evaluate and confirm the reaction pathway.
- Asadbegi, Sajad,Mobinikhaledi, Akbar,Bodaghifard, Mohammad Ali
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- Multicomponent Synthesis of 4-Alkyl(Aryl, Hetaryl)-2-alkoxycarbonyl(aroyl, carbamoyl)- 3,6-diamino-5-cyanothieno[2,3-b]pyridines
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The condensation of malononitrile with hydrogen sulfide and aldehydes in the presence of triethylamine in ethanol at room temperature afforded 4-alkyl(aryl, hetaryl)-2,6-diamino-3,5-dicyano-4H-thiopyrans. Treatment of the latter in situ with alkali in DMF, followed by addition of an alkylating agent, led to the formation of 4-alkyl(aryl, hetaryl)-2-alkoxycarbonyl(aroyl, carbamoyl)-3,6-diamino-5-cyanothieno[2,3-b]- pyridines.
- Dyachenko,Dyachenko,Dorovatovskii,Khrustalev,Nenajdenko
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p. 1435 - 1445
(2019/01/04)
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- A convenient electro-catalyzed multicomponent synthesis of 4: H -thiopyran derivatives
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An environmentally benign synthesis of substituted 4H-thiopyrans was carried out by the condensation of aromatic aldehydes, malononitrile, carbon disulfide and primary amines. Constant potential electro synthesis was carried out in an undivided cell at ro
- Dubey, Rahul,Singh, Vinay K.,Sharma, Laxmi Kant,Upadhyay, Abhishek,Kumar, Narendra,Singh, Rana Krishna Pal
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supporting information
p. 7836 - 7839
(2017/08/14)
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- Bis(4-pyridylamino)triazine-stabilized magnetite nanoparticles: preparation, characterization and application as a retrievable catalyst for the green synthesis of 4H-pyran, 4H-thiopyran and 1,4-dihydropyridine derivatives
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Synthesis of bis(4-pyridylamino)triazine stabilized on silica-coated nano-Fe3O4 particles, and their feasibility as a reusable heterogeneous basic catalyst are reported. The catalytic performance of this novel material was studied fo
- Bodaghifard,Mobinikhaledi,Asadbegi
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- ACETYL-COA CARBOXYLASE MODULATORS
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Provided herein are compounds that exhibit activity as acetyl-CoA carboxylase modulators (e.g., inhibitors) and are useful, for example, in methods for the control of fungal pathogens in plants.
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Paragraph 00256-00260
(2015/01/09)
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- Novel [4 + 2] cycloaddition reaction of aryl-methylidenemalononitriles to unsaturated chalcogen amides. Synthesis, structure, and properties of triethylammonium 3,5,5-tricyano-1,4,5,6-tetrahydropyridine-2-selenolates and -thiolates
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Reaction of arylmethylidenemalononitriles with 3-aryl-2-cyanoprop-2- eneselenoamides in the presence of Et3N gave triethylammonium 4,6-diaryl-3,5,5-tricyano-1,4,5,6-tetrahydropyridine-2-selenolates. A similar reaction with cyclohexylidenecyanothioacetamide yields triethylammonium 4-aryl-1,5,5-tri-cyano-3-azaspiro[5.5]undec-1-ene-2-thiolate. Alkylation of the obtained selenolates and thiolates gives 6-(alkylseleno)-2,4-diaryl-1,4- dihydropyridine-3,3,5(2H)-tricarbonitriles and 4-(alkylthio)-2-aryl-3-aza- spiro[5.5]undec-4-ene-1,1,5-tricarbonitriles, respectivelly. The structure of 2,4-di(2-furyl)-6-{[2-(4-methylphenyl)-2-oxoethyl]seleno}-1,4-dihydropyridine-3, 3,5(2H)-tricarbonitrile has been confirmed by the X-ray structural analysis.
- Frolov,Dotsenko,Krivokolysko,Kostyrko
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p. 1289 - 1300
(2014/01/17)
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- Organocatalysis in synthesis: L-proline as an enantioselective catalyst in the synthesis of pyrans and thiopyrans
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The multicomponent reaction (MCR) of aromatic aldehydes 1 and malononitrile (2) with active methylenes 5a-h in the presence of L-proline produced pyrans and thiopyrans 6a-h stereospecifically and in good yields. Moreover a novel MCR of ethyl propiolate (8) with 1 and 2 in the presence of L-proline to afford (R)-polysubstituted pyran is also reported. X-ray structures, e.e. and optical activity of the synthesized compounds indicated that L-proline as a catalyst is responsible for the observed enantioselectivity in the studied reactions.
- Hilmy Elnagdi, Noha M.,Al-Hokbany, Noura Saad
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experimental part
p. 4300 - 4312
(2012/07/28)
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- MWI-promoted preparation of 4H-thiopyran derivatives through one-pot multi-component reactions
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One-pot reaction of aromatic aldehydes, cyanothioacetamide and malononitrile under microwave irradiation proved to be an efficient way for the synthesis of 2,6-diamino-4-aryl-4H-thiopyran-3,5-dicarbonitriles without any added catalyst.
- Fan, Xuesen,Wang, Xia,Zhang, Xinying,Li, Xiaoyan,Qu, Guirong
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p. 693 - 695
(2008/09/21)
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- CYCLIZATION OF NITRILES. XXX. SYNTHESIS, STRUCTURE, AND PROPERTIES OF 6-AMINO-4-ARYL(HETEROARYL)-3,5-DICYANO-2(1H)-PYRIDINETHIONES
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The reactions of arylmethylenecyanothioacetamides with malononitrile and of arylmethylenemalononitriles with cyanothioacetamide take place regioselectively with the formation of 6-amino-4-aryl-3,5-dicyano-2(1H)-pyridinethiones and not 5-arylmethylene-4,6-diamino-3-cyanopyridine-2-thiones.The 6-amino-4-aryl-3,5-dicyano-2(1H)-pyridinethiones are formed by the recyclization of the 4-aryl-2,6-diamino-3,5-dicyano-4H-thiopyranes.
- Sharanin, Yu. A.,Promomenkov, V. N.,Shestopalov, A. M.,Nestorov, V. N.,Malenchuk, S. N.,et al.
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p. 560 - 565
(2007/10/02)
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- CYCLIZATION OF NITRILES. XXXIII. SYNTHESIS AND STRUCTURE OF 4-ARYL-2,6-DIAMINO-3,5-DICYANOTHIOPYRANS AND THEIR RECYCLIZATION TO 6-AMINO-4-ARYL-3,5-DICYANO-2(1H)-PYRIDINETHIONES
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Like the three-component condensation of aromatic aldehydes, malononitrile, and cyanothioacetamide, the reaction of arylidenemalononitriles with cyanothioacetamide and of arylidenecyanothioacetamides with malononitrile leads to the formation of 4-aryl-2,6-diamino-3,5-dicyano-4H-thiopyrans.It was established by x-ray crystallographic investigation that the 4H-thiopyran ring in the obtained compounds has the boat conformation.Under the influence of bases the 4H-thiopyrans readily undergo recyclization to 6-amino-4-aryl-3,5-dicyano-2(1H)-pyridinethiones.
- Sharanin, Yu. A.,Shestopalov, A. M.,Nesterov, V. N.,Melenchuk, S. N.,Promonenkov, V. K.,et al.
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p. 1189 - 1196
(2007/10/02)
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- Activated Nitriles in Heterocyclic Synthesis: The Reaction of Cyanothioacetamide with Activated Double Bond Systems
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Die Reaktion von Benzylidenmalononitrilen mit Cyanthioacetamid (1) ergibt je nach den Reaktionsbedingungen entweder Thiopyrane oder Pyridine.Die Strukturen der Reaktionsprodukte wurden mittels 13C-NMR aufgeklaert.
- Galil, Fathy Mohamed Abdel,Sallam, Mohamed Mohamed,Sherif, Sherif Mourad,Elnagdi, Mohamed Hilmy
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p. 1639 - 1644
(2007/10/02)
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- Nitriles in Heterocyclic Synthesis: Novel Synthesis of 4H-Thiopyran and of 2-Hydroxy-6-pyridine Thione Derivatives
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Reaction of arylmethylenemalononitrile 2a-c with cyanothioacetamide 1 afforded 4-aryl-2,6-diamino-4H-thiopyran-3,5-dicarbonitriles 5a-c on refluxing in ethanolic aqueous triethylamine, rearranged to yield the 4-aryl-1,2-dihydro-6-hydroxy-2-thioxo-3,5-pyridine dicarbonitriles 8a-c.The same compounds could be obtained on treatment of 2a-c with 1 in ethanolic aqueous triethylamine or on reacting 1 with 2d-f.The 13C NMR data of the products are reported and interpreted. - Keywords: Cyanothioacetamide, 2-Aminothiopyranes, Pyridine Thiones, 13C NMR Spectra
- Elgemeie, Galal Eldin Hamza,Sherif, Sherif Mourad,Aal, Fatma Abd El Maksoud Abd El,Elnagdi, Mohamed Hilmy
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p. 781 - 783
(2007/10/02)
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- A NOVEL SYNTHESIS OF 4-H-THIOPYRANS : UNEXPECTED PRODUCTS OF REACTION OF CYANOTHIOACETAMIDE WITH CINNAMONITRILE DERIVATIVES
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The reaction of arylidenemalononitrile with cynothioacetamide afforded either thiopyrans or pyridine derivatives depending on reaction conditions. 13 C NMR was utilised to elucidate the proposed structures of the reaction products.
- Elgemeie, Galal Eldin Hamza,Sallam, Mohamed Mohamed Mohamed,Sherif, Sherif Mourad,Elnagdi, Mohamed Hilmy
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p. 3107 - 3110
(2007/10/02)
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