- Cu(II)-Promoted Cascade Synthesis of Fused Imidazo-Pyridine-Carbonitriles
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A Cu(II)-promoted synthesis of an aza-fused N-heterocycle having a benz-imidazopyridine scaffold is developed via an addition-cyclization reaction followed by an Ullmann-type C-N coupling between o-iodoanilines and γ-ketodinitriles. This protocol features a broad substrate scope, giving products in 32-84% yields. The compounds show excellent photoluminescence properties having two absorption maxima in the region between 270-280 and 338-350 nm and emission maxima in the range of 502-533 nm. The HOMO-LUMO energy gap of 3.49-3.57 eV was determined using Gaussian 09 at the B3LYP/6-31G (d, p) basis set level. We also demonstrated a few postsynthetic modifications.
- Rakshit, Amitava,Dhara, Hirendra Nath,Alam, Tipu,Dahiya, Anjali,Patel, Bhisma K.
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supporting information
p. 17504 - 17510
(2021/11/18)
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- Visible-light-accelerated pd-catalyzed cascade addition/ cyclization of arylboronic acids to γ- And β-ketodinitriles for the construction of 3-cyanopyridines and 3-cyanopyrrole analogues
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The one-pot synthetic strategies for 2,4,6-triarylnicotinonitriles and 2,5-diaryl-1H-pyrrole-3-carbonitriles have been accomplished via a Pd-catalyzed coupling of arylboronic acid with 2-(3-oxo-1,3-diarylpropyl)malononitrile and 2-(2-oxo-2- arylethyl)malo
- Patel, Bhisma K.,Rakshit, Amitava,Kumar, Prashant,Alam, Tipu,Dhara, Hirendranath
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p. 12482 - 12504
(2020/11/09)
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- Conjugate addition of malononitrile on chalcone: Biocatalytic [Formula presented] bond formation
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An efficient, cost effective and environmentally friendly protocol has been developed for the Michael addition of malononitrile on 1,3-diaryl-2-propen-1-ones (Chalcones) using very cheaper, easily available natural catalyst, baker's yeast. The whole cells of yeast excellently worked in nonaqueous medium, ethanol without decrease in catalytic activity.
- Punyapreddiwar, Nitesh D.,Zodape, Sangesh P.,Wankhade, Atul V.,Pratap, Umesh R.
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p. 124 - 126
(2016/08/23)
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- One-Pot Quinine-Catalyzed Synthesis of α-Chiral γ-Keto Esters: Enantioenriched Precursors of cis-α,γ-Substituted-γ-Butyrolactones
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A highly enantioselective one-pot synthesis of important building blocks, α-chiral γ-keto esters, has been developed by combining a quinine-catalyzed Michael addition of malononitrile to trans-enones followed by magnesium monoperoxyphthalate (MMPP) oxidat
- Meninno, Sara,Volpe, Chiara,Lattanzi, Alessandra
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supporting information
p. 2845 - 2848
(2016/09/13)
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- Immobilization of lipase on Fe3O4/ZnO core/shell magnetic nanoparticles and catalysis of Michael-type addition to chalcone derivatives
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Fe3O4/ZnO core/shell magnetic nanoparticles in 1:1 and 1:2 molar ratios were prepared and characterized by using X-ray powder diffraction, scanning electron microscopy, thermogravimetric analysis, FT-IR spectra, and flame atomic abso
- Ghasemi, Sabrieh,Heidary, Marjan,Faramarzi, Mohammad Ali,Habibi, Zohreh
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p. 121 - 128
(2014/01/23)
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- A mild and convenient one-pot synthesis of 4,6-diaryl- 3-aminoisoxazolo[3, 4-b]pyridines
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We have developed a convenient method for the synthesis of a series of new 4,6-diaryl-3-aminoisoxazolo[3,4-b]pyridines through one-pot reaction starting from the easily available chalcones, malononitrile, and hydroxylamine. This class of compounds might h
- Miao, Chun-Bao,Wang, Yan-Hong,Dong, Chun-Ping,Yang, Hai-Tao,Meng, Qi,Sun, Xiao-Qiang
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p. 2599 - 2605
(2014/01/06)
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- An active and selective heterogeneous catalytic system for Michael addition
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Potassium fluoride doped natural zeolite was found to be an efficient and selective solid base catalyst for 1,4-Michael addition. The catalyst is easily prepared and the workup procedure simplified by simple filtration. All products were obtained in high
- Keipour, Hoda,Khalilzadeh, Mohammad A.,Hosseini, Abolfazl,Pilevar, Afsaneh,Zareyee, Daryoush
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experimental part
p. 537 - 540
(2012/06/29)
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- The Michael addition of active methylene compounds to chalcone derivatives using a catalytic amount of iodine and K2CO3 at room temperature
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A convenient method for the Michael addition of active methylene compounds to chalcone derivatives has been developed using the inexpensive and environmentally friendly reagent I2/K2CO3 at room temperature. The method is m
- Ren, Yi-Ming,Cai, Chun
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experimental part
p. 176 - 178
(2011/07/31)
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- A facile and efficient one-pot synthesis of polysubstituted benzenes in guanidinium ionic liquids
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A facile and efficient synthesis of polysubstituted benzenes has been developed via sequential Michael addition, Knoevenagel condensation and nucleophilic cyclization reactions of readily available chalcones with active methylene compounds in guanidinium
- Xin, Xin,Wang, Yan,Xu, Wu,Lin, Yingjie,Duan, Haifeng,Dong, Dewen
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body text
p. 893 - 898
(2010/09/05)
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- Back to natural cinchona alkaloids: Highly enantioselective Michael addition of malononitrile to enones
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An efficient and convenient highly enantioselective Michael addition of malononitrile to enones has been developed by using quinine as the organocatalyst. The adducts were isolated in excellent yield and high asymmetric induction (up to 95% ee). An easy r
- Russo, Alessio,Perfetto, Alessandra,Lattanzi, Alessandra
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supporting information; experimental part
p. 3067 - 3071
(2010/04/06)
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- Michael addition of active methylene compounds to α, β-unsaturated carbonyl compounds under the influence of molecular sieves in dimethyl sulfoxide
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The Michael addition of active methylene compounds to α, β-unsaturated carbonyl compounds in the presence of MS 4A in dimethyl sulfoxide proceeds smoothly to afford the corresponding 1,4-addition products in good to high yields. Copyright
- Kakinuma, Tomoko,Chiba, Ryoichi,Oriyama, Takeshi
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experimental part
p. 1204 - 1205
(2009/12/01)
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- Natural phosphate modified with lithium nitrate: A new efficient catalyst for the construction of carbon-carbon, carbon-sulfur, and carbon-nitrogen bonds
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The addition of small amounts of lithium nitrate to natural phosphate followed by calcination gives a new catalyst Li/NP (weight ratio LiNO3/NP = 1/15). This material showed catalytic activity in the Michael addition of amines, mercaptans, and active methylene compounds to chalcone derivatives with high yields under mild reaction conditions. Li/NP is used as the catalyst for a facile synthesis of -amino acids, -sulfur acids, and 4 H-chromenes under heterogeneous conditions. The usual, undesirable byproducts from the Michael condensation such as 1,2-addition, bis-addition, and polymerization compounds are not observed with this method. The work-up procedure is simplified by simple filtration with the use of Li/NP.
- Zahouily, Mohamed,Mounir, Bahija,Cherki, Hind,Bahlaouan, Bouchaib,Rayadh, Ahmed,Sebti, Said
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p. 1203 - 1217
(2008/02/02)
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- Natural phosphate doped with potassium fluoride: Efficient catalyst for the construction of a carbon-carbon bond
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Natural phosphate-doped catalyst was found to be an efficient, environmentally attractive, and selective solid base catalyst for 1,4-Michael addition. The products of undesirable side reactions resulting from 1,2-adddition, polymerization, and bis-additio
- Zahouily, Mohamed,Bahlaouan, Bouchaib,Aadil, Mina,Rayadh, Ahmed,Sebti, Said
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p. 275 - 278
(2013/09/04)
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- Samarium(III) iodide promoted three-component coupling reactions of aldehydes, α-haloketones, and active methylene or methyl compounds
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In the presence of samarium(III) iodide, the reaction of aldehydes, α-haloketones with malononitrile, ethylcyanoacetate or nitromethane proceeded very efficiently and furnished moderate to high yields of adducts.
- Ma, Yongmin,Zhang, Yongmin
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p. 711 - 715
(2007/10/03)
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- A novel tandem reaction of chalcone with malononitrile or ethylcyanoacetate promoted by samarium (III) iodide and followed by samarium (II) iodide
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Michael additions of active methylene compounds (for example: malononitrile, ethylcyanoacetate) to chalcones promoted by Sm3 gave 1,4-adducts which, after intramolecular coupling reactions induced by Sm2, furnished fine yields of cyc
- Ma, Yongmin,Zhang, Yongmin
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p. 288 - 290
(2007/10/03)
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