- Synthesis and crystal structures of 2-amino-4-methyl-5,6,7,8-tetrahydroquinoline-3-carbonitrile and 2-amino-4-phenyl-4a,5,6,7-tetrahydro-4H-naphthalene-1,3,3-tricarbonitrile
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2-Amino-4-methyl-5,6,7,8-tetrahydroquinoline-3-carbonitrile with m.f. C11H13N3 was synthesized using simple multicomponent reaction of cyclohexanone, malononitrile and acetaldehyde. However, in an effort to synthesize anot
- Saddiqa, Aisha,Bukhari, Iftikhar Hussain,Tahir, Muhammad Nawaz,Ahmad, Matloob,Shafiq, Muhammad,Arshad, Muhammad Nadeem
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- Synthesis of cobalt tetra-2,3-pyridiniumporphyrazinato with sulfonic acid tags as an efficient catalyst and its application for the synthesis of bicyclic: Ortho -aminocarbonitriles, cyclohexa-1,3-dienamines and 2-amino-3-cyanopyridines
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Cobalt tetra-2,3-pyridiniumporphyrazinato with sulfonic acid tag [Co(TPPASO3H)]Cl was produced and catalyzed the synthesis of ortho-aminocarbonitriles, cyclohexa-1,3-dienamines and 2-amino-3-cyanopyridines. The synthesis of 2-amino-3-cyanopyridines by usi
- Baghery, Saeed,Dashteh, Mohammad,Khazaei, Ardeshir,Makhdoomi, Sajjad,Safaiee, Maliheh,Yarie, Meysam,Zolfigol, Mohammad Ali
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p. 27824 - 27834
(2020/08/17)
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- Synthesis of 1H-isochromenes, 4H-chromenes, and ortho-aminocarbonitrile tetrahydronaphthalenes from the same reactants by using metal-free catalyst
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A facile and rapid multicomponent synthesis of pharmaceutically diverse 1H-isochromenes, 4H-chromenes, and ortho-aminocarbonitrile tetrahydronaphthalenes has been developed from benzaldehyde, malononitrile, and cyclohexanone. Three different methods from the same reactants, solvent, temperature, and catalyst lead to three products with excellent yields. All the reactions were followed with the Michael addition and cyclization. In this study, morpholine was used as an active metal-free base catalyst that increases the yields of products and decreases the time of reactions.
- Naeimi, Hossein,Mohammadi, Somaye
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- A task-specific biodegradable ionic liquid: a novel catalyst for synthesis of bicyclic ortho-aminocarbonitriles
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Abstract: Herein, we report a novel method for synthesis of bicyclic ortho-aminocarbonitriles catalyzed by biodegradable ionic liquid. The biodegradability (BOD analysis) of all the ionic liquids that are used to carry out the reaction is studied, and the
- Gaikwad,Undale,Patil,Patravale,Kamble
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p. 1175 - 1180
(2018/05/22)
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- Multicomponent domino reactions in deep eutectic solvent: An efficient strategy to synthesize multisubstituted cyclohexa-1,3-dienamines
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The multicomponent domino reactions of ketones, aldehydes and malononitrile in a deep eutectic solvent (DES) were developed. Urea-choline chloride based DES is effective dual solvents/organocatalysts and affording a series of multisubstituted cyclohexa-1,
- Azizi, Najmedin,Ahooie, Tahereh Soleymani,Hashemi, Mohammad Mahmoudi
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p. 221 - 224
(2017/09/28)
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- DABCO: An efficient catalyst for pseudo multi-component reaction of cyclic Ketone, Aldehyde and Malononitrile
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Designing efficient methods for the synthesis of complex molecules with predefined functionalities is a challenging task in modern organic chemistry. In this context, multicomponent reactions (MCRs), by virtue of their applications, constitute a central a
- Chinchkar, Sarika M.,Patil, Jayavant D.,Korade, Suyog N.,Gokavi, Gavisiddappa S.,Shejawal, Rajendra V.,Pore, Dattaprasad M.
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supporting information
p. 403 - 408
(2017/07/24)
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- DABCO functionalized dicationic ionic liquid (DDIL): A novel green benchmark in multicomponent synthesis of heterocyclic scaffolds under sustainable reaction conditions
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A novel DABCO functionalized dicationic ionic liquid (DDIL) has been synthesized using diazabicyclo[2,2,2]octane (DABCO), 1,3-dichloro-2-propanol and NaBF4 in acetonitrile. The IL was fully characterized by IR, NMR and mass spectroscopic techniques. The presence of BF4? anion in IL was confirmed by 19F NMR and also supported by mass analysis. The TGA analysis showed that the IL is thermally stable up to 180?°C temperature. We demonstrated that the presence of the tertiary nitrogen sites and hydroxyl group in the DDIL network enhances the overall activity of DDIL. These make them compatible for base catalyzed one pot multicomponent synthesis of ortho-amino carbonitriles and 3-methyl-4-arylmethylene-isoxazol-5(4H)-ones under grinding without solvent. In addition the activity of DDIL was also studied for synthesis of tetrahydrobenzo[b]pyrans under ultrasound irradiation in water. Furthermore the DDIL was easily recoverable and recyclable many times with modest decrease in activity.
- Lohar, Trushant,Kumbhar, Arjun,Barge, Madhuri,Salunkhe, Rajshri
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p. 1102 - 1108
(2016/11/09)
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- Facile one-pot synthesis of novel ortho-aminocarbonitriles and dicyanoanilines fused to heterocycles via pseudo four-component reactions
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1-Methylpiperidin-4-one and its sulfur and oxygen analogues undergo individual facile pseudo four-component reactions with two folds of malononitrile and various aldehydes by using ultrasonic irradiation and deficient quantities of pyrrolidine. As a conse
- Mojtahedi, Mohammad M.,Pourabdi, Ladan,Abaee, M. Saeed,Jami, Hamed,Dini, Masoud,Halvagar, Mohammad R.
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p. 1699 - 1705
(2016/03/08)
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- Noncovalent catalysis of glucose-containing imidazolium salt in solvent-free one-pot synthesis of Ortho-aminocarbonitriles
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Abstract A glucose-containing imidazolium salt β-1-imidazole-2,3,4,6-tetraacetyl-D-glucopyranosyl bromide was firstly used as efficient noncovalent organocatalyst to promote the solvent-free preparation of ortho-aminocarbonitriles via a four-component con
- Zhang, Li-Zhuo,Wan, Yu,Zhang, Xiao-Xiao,Cui, Hao,Zou, Huan,Zhou, Qiu-Ju,Wu, Hui
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supporting information
p. 4934 - 4937
(2015/07/28)
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- Tandem synthesis of bicyclic ortho-aminocarbonitrile derivatives in ionic liquids
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An efficient synthesis of 2-amino-4a,5,6,7-tetrahydronaphthalene-1,3,3(4H)-tricarbonitriles via the tandem four-component condensation of one equivalent of aromatic aldehyde, cyclohexanone, and two equivalents of malononitrile in ionic liquids was underta
- Wan,Zhang,Zhao,Wang,Chen,Liu,Huang,Yue,Zhang,Wu
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p. 623 - 627
(2015/03/30)
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- 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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p. 5288 - 5305
(2013/07/19)
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- Primary 1,2-diamine catalysis III: An unexpected domino reaction for the synthesis of multisubstituted cyclohexa-1,3-dienamines
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The first organocatalyzed multicomponent domino reactions of aryl ketones, aldehydes and malononitrile were carried out successfully to afford multisubstituted cyclohexa-1,3-dienamines in satisfactory yields.
- Wang, Junfeng,Li, Qin,Qi, Chao,Liu, Yi,Ge, Zemei,Li, Runtao
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supporting information; experimental part
p. 4240 - 4242
(2010/11/18)
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- Nitriles in Organic Synthesis: The Reaction of Cinnamonitriles with Cyclohexanone and Acetylacetone
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The reaction of 1a,b with cyclohexanone afforded hexahydronaphthalene derivatives (3a,b).In contrast to the behaviour of 1a,b, cyclohexanone reacts with 4a-c to yield the propenylidenecyclohexanone derivatives (5a-c).The reaction of 1a with acetylacetone
- El-Sakka, I. A.,El-Kousy, S. M.
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p. 345 - 350
(2007/10/02)
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- CYCLIZATION REACTIONS OF NITRILES. III. SYNTHESIS OF o-CYANOANILINES BY THE THORPE REACTION
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The reaction of alkylidenemalononitriles with arylidene derivatives of malononitrile and cyanoacetic ester leads to the formation of derivatives of 1-amino-2,6-dicyano-3,5-diaryl-1,3-cyclohexadiene or 2,4-dicyano-3-amino-5-arylbicyclodeca-2,10-dien
- Sharanin, Yu. A.,Baskakov, Yu. A.,Abramenko, Yu. T.,Putsykin, Yu. G.,Vasil'ev, A. F.,Nazarova, E.B.
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p. 1870 - 1879
(2007/10/02)
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