- A convenient synthesis of 2,4-diarylpolyhydroquinoline derivations in the presence of ammonium acetate
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A series of substituted 5-oxo-1,2,3,4,5,6,7,8-octahydroquinoline derivatives have been synthesized from 5,5-dimethyl-1,3-cyclohexane-dione (dimedone) and 1,3-diaryl-2-propen-1-one in DMF at 80°C in the presence of ammonium acetate with high yields (64-98%
- Wang, Xiang-Shan,Shi, Da-Qing,Tu, Shu-Jiang
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- Silica-supported perchloric acid (HClO4-SiO2): A mild, reusable and highly efficient heterogeneous catalyst for multicomponent synthesis of 1,4-dihydropyridines via unsymmetrical Hantzsch reaction
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Facile synthesis of some 1,4-dihydropyridine derivatives via Hantzsch reaction of 5,5-dimethyl-1,3-cyclohexanedione (dimedone), 1,3-diphenyl-2-propen- 1-one derivatives and ammonium acetate under solvent-free condition in the presence of silica-supported perchloric acid (HClO4-SiO2) is described. The catalyst is easily prepared, stable, reusable and efficient under the reaction conditions.
- Mansoor, Syed Sheik,Aswin, Krishnamoorthy,Logaiya, Kuppan,Sudhan, Prasanna Nitiya,Malik, Saleem
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- Synthesis and crystal structure of 7,7-dimethyl-2,4-diphenyl-5-oxo-1,4,5,6,7,8-hexahydroquinolin
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The 7,7-dimethyl-2,4-diphenyl-5-oxo-1,4,5,6,7,8-hexahydroquinolin was synthesized and the compound was identified by IR, 1H NMR, elemental analysis and X-ray crystallography. It crystallized in the triclinic space group P1, with a = 7.129(2) A, b = 10.514(3) A, c = 13.040(3) A, α = 76.58(2)°, β = 88.97(2)°, γ = 79.24(2)°, and Dcalc = 1.172 g cm-3 for Z = 2. X-ray analysis revealed that the atoms C(2), C(3), C(4), C(10), C(9), and N form a six-membered ring that adopts a boat conformation, and another six-membered ring (C(10)-C(9)-C(8)-C(7)-C(6)-C(5)) adopts a half-chair conformation. In addition, there is an intermolecular hydrogen bond (N-H0 ... O) in the product molecule.
- Wang, Xiangshan,Shi, Daqing,Tu, Shujiang
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- Efficient synthesis of 2,4-diaryl hexahydroquinoline-5-one derivatives in the presence of triethylamine
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Abstract A convenient and efficient protocol for the synthesis of 2,4-diaryl hexahydroquinoline-5-one derivatives has been accomplished by a three-component reaction of 1,3-diaryl-2-propen-1-ones, dimedone and ammonium acetate catalyzed by triethylamine under solvent-free conditions. The simple experimental procedure, use of an inexpensive catalyst, short reaction times, and excellent yields make this procedure facile, practical, and sustainable.
- Karimi-Jaberi, Zahed,Azadi, Maryam
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p. 6741 - 6747
(2015/02/19)
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- Regiospecific ring closure reactions of 1, 3-diphenylthiobarbituric acid and dimedone: Formation of spiro vs fused heterocycles
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The one pot reaction of 1, 3-diphenylthiobarbituric acid with benzylidene acetophenone, benzaldehyde and ammonium acetate in presence of catalytic amount of acetic acid furnishes regiospecifically an azaspiro compound. The azaspiro compound has also been
- Pati, Anita,Majumdar, Poulomi,Garnayak, Sarita,Behera, Ajaya K.,Behera, Rajani K.
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p. 384 - 391
(2014/05/06)
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- New 5-unsubstituted dihydropyridines with improved CaV1.3 selectivity as potential neuroprotective agents against ischemic injury
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C5-unsubstituted-C6-aryl-1,4-dihydropyridines were prepared by a CAN-catalyzed multicomponent reaction from chalcones, β-dicarbonyl compounds, and ammonium acetate. These compounds were able to block Ca2+ entry after a dep
- Tenti, Giammarco,Parada, Esther,León, Rafael,Egea, Javier,Martínez-Revelles, Sonia,Briones, Ana María,Sridharan, Vellaisamy,López, Manuela G.,Ramos, María Teresa,Menéndez, J. Carlos
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p. 4313 - 4323
(2014/06/09)
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- Para substituted benzaldehydes as expedient reagents for the oxidative aromatization of hydroquinoline
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A Cannizzaro-type reaction of tetrahydro-5(1H)-quinolinones with para substituted benzaldehydes in the presence of a base formed the corresponding quinoline and aryl methanol rather than arylidene derivatives because of the oxidation of tetrahydroquinoline and reduction of benzaldehydes as a result of unprecedented hydride transfer from tetrahydroquinoline to arylaldehydes. The reaction proceeds best with the participation of substituents with +M effect in substrate molecule.
- Majumdar, Poulomi,Pati, Anita,Behera, Rajani K.,Behera, Ajaya Kumar
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p. 703 - 712
(2013/07/05)
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- Cobalt nanoparticles promoted highly efficient one pot four-component synthesis of 1,4-dihydropyridines under solvent-free conditions
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A straightforward and general method has been developed for the synthesis of C5-unsubstitiuted 1,4-dihydropyridines by a reaction using dimedone, acetophenone, aromatic aldehydes, and ammonium acetate in the presence of a catalytic amount of Co nanopartic
- Safari, Javad,Banitaba, Sayed Hossein,Dehghan Khalili, Shiva
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experimental part
p. 1850 - 1855
(2012/02/16)
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- Design and synthesis of 2,4-disubstituted polyhydroquinolines as prospective antihyperglycemic and lipid modulating agents
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A series of 2,4-disubstituted polyhydroquinoline were synthesized and evaluated for their in vivo antihyperglycemic as well as antidyslipidemic activities. Several synthesized compounds have exhibited promising in vivo antihyperglycemic in SLM, STZ-S, and db/db mice model along with significant lipid and TG modulating activity. All these compounds were evaluated in various in vitro models of diabetes to know the possible mechanism of their antihyperglycemic action. Interestingly, compounds 3a-r (diaryl substitution) have exhibited promising protein-tyrosine phosphatase 1B (PTP1B) inhibitory activity whereas, compounds 5a-d (acid substituted) have shown significant glycogen phosphorylase activity.
- Kumar, Atul,Sharma, Siddharth,Tripathi, Vishwa Deepak,Maurya, Ram Awatar,Srivastava, Swayam Prakash,Bhatia, Gitika,Tamrakar,Srivastava, Arvind Kumar
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experimental part
p. 4138 - 4148
(2010/08/06)
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- A facile and expeditious microwave-assisted synthesis of 4-aryl-2-ferrocenyl-quinoline derivatives via multi-component reaction
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An efficient and rapid route for the synthesis of 4-aryl-2-ferrocenyl-quinoline derivatives through microwave-assisted multi-component reaction of acetylferrocene with aromatic aldehyde and dimedone in the presence of ammonium acetate using DMF as reactio
- Tu, Shu-Jiang,Yan, Shu,Cao, Xu-Dong,Wu, Shan-Shan,Zhang, Xiao-Hong,Hao, Wen-Juan,Han, Zheng-Guo,Shi, Feng
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experimental part
p. 91 - 96
(2009/03/12)
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- A facile and green preparation of 2,4-diarylpolyhydroquinolines
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An efficient and environmentally benign procedure for the preparation of 2,4-diarylpolyhydroquinoline derivatives from 5,5-dimethylcyclohexane-1,3-dione, chalcones and ammonium acetate under microwave irradiation in a solvent-free manner is described in t
- Hu, Xueyuan,Zhang, Xinying,Fan, Xuesen,Qu, Guirong,Li, Yanzhen
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p. 697 - 699
(2007/10/03)
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- 5-OXOHEXAHYDROQUINOLINES, CONDENSED ANALOGS OF 1,4-DIHYDROPYRIDINES. PREPARATION AND PROPERTIES
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The optimum conditions for the preparation of 5-oxohexahydroquinolines have been established, and a probable reaction mechanism for their formation is proposed.Some reactions of these compounds have been examined.
- Kazarinova, T. D.,Markova, L. I.,Kharchenko, V. G.
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p. 438 - 441
(2007/10/02)
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