- Prolinamide functionalized polyacrylonitrile fiber with tunable linker length and surface microenvironment as efficient catalyst for Knoevenagel condensation and related multicomponent tandem reactions
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A series of new prolinamide polyacrylonitrile fiber catalysts with tunable length of alkyl linker and different linker group were prepared by covalent bonding for the first time and well characterized by mechanical strength, FT-IR, XRD, EA, TGA, SEM and water contact angel. The catalytic activities of these fiber catalysts were evaluated in Knoevenagel condensation and one-pot Knoevenagel-Michael multicomponent tandem reactions to synthesize α, β-unsaturated nitrile and 2-amino-4H-chromene derivatives in water. The result show that the suitable linker length attaching amines to fiber matrix as well as the constructed hydrophobic microenvironment by linker group within the surface layers of fiber materials effectively promotes the reactions. In addition, the good swollen capacity of fiber in solvent ensure that the reaction proceed well. Fiber catalyst PANPA?2F modified by prolinamide with a C2 alkyl chain exhibited the best catalytic performance and can be easily recovered and reused for at least ten consecutive cycles without significant loss of catalytic activity and active sites leaching.
- Zhu, Hai,Xu, Gang,Du, Huimin,Zhang, Chenlu,Ma, Ning,Zhang, Wenqin
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p. 217 - 229
(2019/05/16)
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- Asymmetric Reaction of p-Quinone Diimide: Organocatalyzed Michael Addition of α-Cyanoacetates
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Hitherto unknown catalytic enantioselective transformation of p-quinone diimides is achieved using chiral bifunctional organic molecules. Bifunctional thiourea compounds catalyze the Michael addition of cyanoacetates with excellent yields and enantioselec
- Reddy, Sivakumar N.,Reddy, Venkatram R.,Dinda, Shrabani,Nanubolu, Jagadeesh Babu,Chandra, Rajesh
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supporting information
p. 2572 - 2575
(2018/05/17)
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- Isocyanate-functionalized starch as biorenewable backbone for the preparation and application of poly(ethylene imine) grafted starch
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Reactive supports provide versatile platforms for surface decoration, affording various functional materials widely used in chemical and biological research. Considering the biodegradability, biocompatibility, and economy, starch is a suitable support med
- Fu, Lixia,Peng, Yanqing
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p. 1547 - 1554
(2017/07/18)
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- Calcium ferrite, an efficient catalyst for knoevenagel condensation(A green approach)
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Calcium ferrite NPs catalyst have been used as a cheaper and highly efficient catalyst for Knoevenagel condensation of active methylene substrate with various carbonyl compounds affording condensed products in excellent yields in shorter reaction time. Th
- Pippal, Parveen,Singh, Prabal Pratap
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p. 1736 - 1743
(2017/10/27)
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- Stereoselective synthesis of vic-halohydrins and an unusual Knoevenagel product from an organocatalyzed aldol reaction: A non-enamine mode
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Stereoselective synthesis by an aldol reaction between chloroacetone and aldehyde was studied using a synthesized chiral organocatalyst and triethylamine. The reaction gave α-chloro-β-hydroxy ketones in excellent yield with high anti selectivity and enantioselectivity. The chiral organocatalyst was also used in the Knoevenagel reaction, which gave α-cyano-β-hydroxy ketones at a low temperature and the usual Knoevenagel product at a high temperature. Both products were obtained in good to moderate yield with good anti selectivity in the case of α-cyano-β-hydroxy ketone derivatives.
- Thorat,Goswami,Sondankar,Bhusare
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p. 1093 - 1100
(2015/07/01)
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- Discovery, stereospecific characterization and peripheral modification of 1-(pyrrolidin-1-ylmethyl)-2-[(6-chloro-3-oxo-indan)-formyl]-1,2,3,4-tetrahydroisoquinolines as novel selective κ opioid receptor agonists
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A novel series of 1-(pyrrolidin-1-ylmethyl)-2-[(3-oxo-indan)-formyl]-1,2,3,4-tetrahydroisoquinoline derivatives maj-3a-maj-3u were synthesized and evaluated in vitro for their binding affinity at κ-opioid receptors. Maj-3c displayed the highest affinity for κ-opioid receptors (Ki = 0.033 nM) among all the compounds evaluated. Furthermore, all four stereoisomers of compound 3c were prepared, and (1S,18S)-3c was identified as the most potent (Ki = 0.0059 nM) κ-opioid receptor agonist among the four stereoisomers. Maj-3c produced significant antinociception (ED50 = 0.000406 mg kg-1) compared to U-50,488H and original BRL 52580 in the acetic acid writhing assay, but its strong sedative effect (ED50 = 0.000568 mg kg-1) observed in the mouse rotation test reduced its druggability. To minimize the central nervous system side effects, a series of hydroxyl-containing analogs of maj-3c were synthesized, and maj-11a was found to be a potent κ-opioid receptor agonist (Ki = 35.13 nM). More importantly, the dose for the sedative effect (ED50 = 9.29 mg kg-1) of maj-11a was significantly higher than its analgesic dose (ED50 = 0.392 mg kg-1), which made it a promising peripheral analgesic candidate compound with weak sedative side effects.
- Gan, Zong-Jie,Wang, Yu-Hua,Xu, Yun-Gen,Guo, Ting,Wang, Jun,Song, Qiao,Xu, Xue-Jun,Hu, Shi-Yuan,Wang, Yu-Jun,Wang, De-Chuan,Sun, De-Zhu,Zhang, Di,Xi, Tao,Li, Hao-Dong,Zhang, Hai-Bo,Hang, Tai-Jun,Lu, Hong-Guo,Liu, Jing-Gen
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p. 5656 - 5673
(2015/05/27)
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- Synthesis and antiproliferative activity in vitro of new 2-aminobenzimidazole derivatives. Reaction of 2-arylideneaminobenzimidazole with selected nitriles containing active methylene group
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A series of pyrimido[1,2-a]benzimidazole and a-cyanocinnamic acid derivatives have been synthesized in the reactions of Schiff bases 2-7 with selected nitriles containing an active methylene group: malononitrile 8-12, cyanoacetamide 13-16, benzyl cyanide 17-21, benzoylacetonitrile 22-24, cyanoacetate methyl ester 25-28 and benzylacetamide 29. The structures 8-29 were confirmed by the results of elementary analysis and their IR, 1H-, 13C-NMR and MS spectra. The products 8-29 of various chemical structure pyrimido[1,2-a] benzimidazole 8-12, 14-16, 17-21, 23-24, 26 and a-cyanocinnamic acid derivatives 13, 22, 25, 27, 28 were obtained, which are of interest for biological studies or which can be substrates for further synthesis. The selected compounds 10, 13, 14, 17, 19, 21, 23-25 and 28 were screened for their antiproliferative activity in vitro against neoplastic and normal cell lines. The most active two compounds were: 2-(o-bromophenylene)-3-cyano-4-phenyl-1,2-dihydropyrimido[1,2-a] benzimidazole (24) and 3-cyano-4-phenyl-2-(2,4-dimethoxyphenyl)-1,2- dihydropyrimido[1,2-a]benzimidazole (23). However, similarly like cisplatin used as the control, they showed no selectivity towards cancer cells, by inhibiting proliferation of normal mouse fibroblasts in similar manner. Versita Sp. z o.o.
- Nowicka, Anna,Liszkiewicz, Hanna,Nawrocka, Wanda P.,Wietrzyk, Joanna,Kempińska, Katarzyna,Dry?, Andrzej
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p. 1047 - 1055
(2014/06/09)
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- Synthesis of on resin poly(propylene imine) dendrimer and its use as organocatalyst
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Solid phase synthesis of poly(propylene imine) dendrimer is described. An iterative synthesis including double Michael addition of acrylonitrile to the primary amino groups on crosslinked polystyrene support followed by reduction of nitrile groups to amin
- Gopalakrishna Panicker, Rajesh Krishnan,Krishnapillai, Sreekumar
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supporting information
p. 2352 - 2354
(2014/05/06)
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- Ammonium fluoride as an inexpensive catalyst for Knoevenagel condensation in solvent-free conditions under microwave irradiation
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Ammonium fluoride (NH4F) has been found to be an inexpensive catalyst for Knoevenagel condensation between aromatic aldehydes 1 and active methylene compounds 2 to afford arylidene derivatives 3 in excellent yields.
- Mogilaiah,Vinay Chandra,Jagadeeshwar,Kavitha
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p. 694 - 697
(2013/07/05)
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- Proximal ester assistance vsstereoelectronic prohibition in catalytic N -acyliminium ion reactions: Stereoselective formation of aza-heterocycles with two contiguous quaternary-tertiary stereocenters
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The catalytic intramolecular and intermolecular -amidoalkylation of deactivated N,O-acetals equipped with either two ester groups or both an ester and a cyano groups to the reactive center has been developed. Reactions in the cyano ester series proceeded
- Saber, Moussa,Comesse, Sébastien,Dalla, Vincent,Netchita?lo, Pierre,Da?ch, Adam
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supporting information; scheme or table
p. 2425 - 2429
(2011/11/04)
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- Synthesis and biological evaluation of 3-amino pyrazolones
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A series of 3-amino-4-(substituted benzylidene)-1H-pyrazol-5(4H)-ones were synthesized by condensation of ethyl-2-cyano-3-(substituted) phenylacrylates with hydrazine hydrate. The chemical structures of synthesized compounds were confirmed by means of IR,
- Rajitha, Galla,Prasad,Bharathi, Koganti
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experimental part
p. 684 - 686
(2011/12/22)
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- Microwave-enhanced Knoevenagel condensation catalysed by NH 2so3NH4
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Ammonium sulphamate catalyses the efficient Knoevenagel condensation of aromatic aldehydes 1 with active methylene compounds in solvent-free conditions under microwave irradiation to give arylidene derivatives 3. The yields are excellent and purity is hig
- Mogilaiah,Babu, H. Sharath,Vidya,Kumar, K. Shiva
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experimental part
p. 390 - 393
(2010/10/18)
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- TETRAHYDRO ISOQUINOLINE DERIVATIVES, PREPARATION METHODS AND MEDICINAL USES THEREOF
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A kind of tetrahydro isoquinoline derivatives (I), their preparation methods, medicine compositions and medicinal uses thereof, especially their uses as κ-opioid receptor excitant in pain relieving, which belongs to the medicine chemistry. The substituents R1, R2, R3, R4 of general formula (I) are defined as the description.
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Page/Page column 9
(2009/04/23)
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- Tetrahydro isoquinoline derivatives, preparation methods and medicinal uses thereof
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A kind of tetrahydro isoquinoline derivatives (I), their preparation methods, medicine compositions and medicinal uses thereof, especially their uses as kappa-opioid receptor excitant in pain relieving, which belongs to the medicine chemistry. The substituents R1, R2, R3, R4 of general formula (I) are defined as the description.
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Page/Page column 6
(2009/12/02)
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- Reaction of ethyl cyanoacetate with benzal-4-acetylanilines: An unexpected result
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Reaction of ethyl cyanoacetate with benzal-4-acetylanilines 1a-10a, the compounds containing both azomethine and ketone linkages, in equimolar ratio, in the presence of pyridine yields solid products, which have been characterized as ethyl benzal-cyanoacetate and its derivatives 1b-10b on the basis of elemental analysis and spectral studies. The reaction of 1a-10a with two moles of ethyl cyanoacetate also results in the formation of the same products 1b-10b, by an unexpected attack of ethyl cyanoacetate on azomethine linkage only rather than on both the reactive centres i.e. carbon-nitrogen double bond and carbon-oxygen double bond.
- Sidhu, Anjali,Rai, Mangat
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p. 778 - 780
(2008/12/20)
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- Efficient green procedure for the Knoevenagel condensation under solvent-free conditions
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Knoevenagel condensation of aromatic aldehydes with active methylene compounds under solvent-free conditions to synthesize arylidene compounds by grinding in the presence of TEBA at room temperature has been described. This method is simple, efficient, an
- Rong, Liangce,Li, Xiaoyue,Wang, Haiying,Shi, Daqing,Tu, Shujiang,Zhuang, Qiya
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p. 2407 - 2412
(2007/10/03)
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- Solvent-free Knoevenagel condensation reaction under microwave irradiation exploiting a new reagent: Antimony trichloride
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A rapid microwave-assisted Knoevenagel condensation exploiting antimony trichloride under solvent-free condition is reported. Several aromatic aldehydes condense with malononitrile and ethyl cyanoacetate within a few minutes in high yields.
- Mitra, Alok Kumar,Karchaudhuri, Nilay,De, Aparna
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p. 177 - 179
(2007/10/03)
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- Low-color ultraviolet absorber compounds and compositions thereof
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Novel ultraviolet absorbing compounds that are liquid in nature, are extremely low in color (and thus permit use without the concomitant necessity of adding large amounts of other coloring agents to combat such discoloring), and are highly effective in pr
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Page/Page column 17
(2010/02/11)
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- Solvent-free synthesis of ethyl α-cyanocinnamate in the presence of CaO
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Ethyl α-cyanocinnamate can be prepared by grinding in the presence of CaO at room temperature. This method is simple, efficient, economical, and environmentally benign.
- Lu, Yeying,Ren, Zhongjiao,Cao, Weiguo,Tong, Weiqi,Gao, Mengfei
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p. 2047 - 2051
(2007/10/03)
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- Microwave assisted Knoevenagel condensation using sodium fluoride and lithium chloride as catalysts under solvent-free conditions
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Microwave assisted Knoevenagel condensation of aromatic aldehydes 1 with active methylene compounds 2 under solvent free conditions to prepare arylidene compounds 3 in excellent yields using cheap and readily available NaF and LiCI as catalysts has been d
- Mogilaiah,Prashanthi,Reddy, G. Randheer,Reddy, Ch. Srinivas,Reddy, N. Vasudeva
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p. 2309 - 2312
(2007/10/03)
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- 7-Methyl trimethoprim analogues as inhibitors of the folate metabolizing enzymes
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A series of 5-(1-phenylethyl)pyrimidines 2-10 (Table I) were designed and synthesized as potent and selective inhibitors of Pneumocystis carinii (P. carinii), Toxoplasma gondii (T. gondii) and Mycobacterium avium (M. avium) dihydrofolate reductases (DHFR)
- Gangjee, Aleem,Lin, Xin,Queener, Sherry F.
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p. 507 - 512
(2007/10/03)
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- A convenient synthesis of 2-amino-5,6,7,8,-tetrahydro-5-oxo-4-aryl-7,7-dimethyl-4H-benzo-[b]- pyran-3-ethylcarboxylates under microwave irradiation
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A series of 2-amino-5,6,7,8-tetrahydro-5-oxo-4-aryl-7,7-dimethyl-4H-benzo-[b] -pyran-3-ethylcarboxylates were synthesized by reaction of β-cyano-β-carbothoxy styrene and 5,5-dimethyl-1,3-cyclo-hexanedione under microwave irradiation without catalyst and s
- Tu,Wang,Feng,Tang,Feng
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p. 2663 - 2666
(2007/10/03)
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- Synthesis and dopaminergic activity of 3-(3,4-dihydroxyphenyl)-1-n-propylpyrrolidine hydrobromide
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3-(3,4-Dihydroxyphenyl)-1-n-propylpyrrolidine hydrobromide was synthesized by a six-step reaction sequence and was evaluated, and compared with apomarphine, for central dopaminergic agonist activity. The compound produced behavioral and biochemical change
- Crider,Hemdi,Hassan,Fahn
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p. 1585 - 1587
(2007/10/02)
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- Reaction of Active Methylene Compounds with Veratraldehyde Schiff Bases and Antifungal Activity of Products
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Michael reaction of veratraldehyde schiff bases with ethyl cyanoacetate, cyanoacetic acid, malonamide, acetylacetone, diethyl malonate, cyanoacetamide and malononitrile gives the addition elimination products, viz. ethyl 3,4-dimethoxybenzalcyanoacetate (2
- Manrao, M. R.,Kaur, Baljit,Sharma, R. C.,Kalsi, P. S.
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p. 1059 - 1060
(2007/10/02)
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