- The Michael addition of active methylene compounds to chalcone derivatives using a catalytic amount of iodine and K2CO3 at room temperature
-
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
-
-
Read Online
- A mild and convenient one-pot synthesis of 4,6-diaryl- 3-aminoisoxazolo[3, 4-b]pyridines
-
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
-
-
Read Online
- Cu(II)-Promoted Cascade Synthesis of Fused Imidazo-Pyridine-Carbonitriles
-
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.
-
supporting information
p. 17504 - 17510
(2021/11/18)
-
- Reaction of 3-Amino-4,6-diarylthieno[2,3-b]pyridine-2-carboxamides with Ninhydrin
-
Abstract: The reaction of N-substituted amides of 3-amino-4,6-diarylthieno[2,3-b]pyridine-2-carboxylic acids with ninhydrin in the presence of catalytic amounts of sulfuric acid gave 1′-spiro[indene-2,2′-pyrido[3′,2′:4,5]thieno[3,2-d]pyrimidine]-1,3,4′(3′
- Aksenov, N. A.,Aksenova, I. V.,Dotsenko, V. V.,Dyadyuchenko, L. V.,Krapivin, G. D.,Lukina, D. Yu.,Muraviev, V. S.,Strelkov, V. D.
-
p. 948 - 960
(2020/07/27)
-
- 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
-
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
-
p. 12482 - 12504
(2020/11/09)
-
- Thieme Chemistry Journals Awardees - Where Are They Now? A Stereoselective Tripeptide Catalyst for Conjugate Addition Reactions of Acetophenones to Dicyanoolefins
-
Peptides of the type H-Pro-Pro-Xaa-NH 2 were evaluated as catalysts for conjugate addition reactions of acetophenones to cyanoolefins. Tripeptide H- d -Pro-Pro-Glu-NH 2 with a carboxylic acid moiety in the side chain of Xaa was ident
- Schnitzer, Tobias,Wennemers, Helma
-
supporting information
p. 1282 - 1286
(2017/06/27)
-
- Chloramphenicol base chemistry. Part 11: chloramphenicol base-derived thiourea-catalyzed enantioselective Michael addition of malononitrile to α,β-unsaturated ketones
-
The first chloramphenicol base-derived thiourea-catalyzed enantioselective Michael addition of malononitrile to α,β-unsaturated ketones is reported. The Michael adducts were obtained in good to excellent yields (up to 98% yield) and enantioselectivities (up to 94% ee). This reaction has a broad substrate scope to various α,β-unsaturated ketones. With this in mind, this methodology was successfully applied to the synthesis of a chiral piperidone, an advanced building block for dihydropyridinone P2X7 receptor antagonists.
- Yan, Linjie,Wang, Haifeng,Xiong, Fangjun,Tao, Yuan,Wu, Yan,Chen, Fener
-
p. 921 - 929
(2017/07/11)
-
- Organocatalytic Enantioselective Decarboxylative Michael Addition of β-Keto Acids to Dicyanoolefins and Disulfonylolefins
-
A convenient organocatalytic enantioselective decarboxylative Michael addition of β-keto acids to dicyanoolefins and disulfonylolefins is realized. In the presence of saccharide-derived chiral amino thioureas, the reaction proceeded smoothly to afford a wide range of the Michael adducts in 62–99% yield with 70–94% ee. Moreover, one of the chiral adducts obtained could be readily converted into the monofluorinated product in a total 68% yield over four steps with 85% ee. (Figure presented.).
- Wei, Yi,Guo, Ran,Dang, Yanfeng,Nie, Jing,Ma, Jun-An
-
p. 2721 - 2726
(2016/09/13)
-
- One-Pot Quinine-Catalyzed Synthesis of α-Chiral γ-Keto Esters: Enantioenriched Precursors of cis-α,γ-Substituted-γ-Butyrolactones
-
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
-
supporting information
p. 2845 - 2848
(2016/09/13)
-
- Conjugate addition of malononitrile on chalcone: Biocatalytic [Formula presented] bond formation
-
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.
-
p. 124 - 126
(2016/08/23)
-
- Quinine catalysed asymmetric Michael additions in a sustainable solvent
-
Diethyl carbonate is shown to be a suitable, sustainable solvent in which to carry out quinine catalysed asymmetric Michael additions of malononitriles to enones. Both malonitrile and α-substituted malononitriles can be used as substrate and the results suggest that π-π stacking interactions between the (hetero)aromatic rings of the catalyst and substrates are important in determining the degree of asymmetric induction.
- Castro-Osma, Jos A.,Comerford, James W.,Heath, Samantha,Jones, Oliver,Morcillo, Maria,North, Michael
-
p. 3678 - 3685
(2015/02/03)
-
- An active and selective heterogeneous catalytic system for Michael addition
-
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
-
experimental part
p. 537 - 540
(2012/06/29)
-
- Ionic-liquid-supported 1,5,7-triazabicyclo[4.4.0]dec-5-ene - An efficient and recyclable organocatalyst for Michael addition to α,β-unsaturated ketones
-
A novel ionic-liquid-supported 1,5,7-triazabicyclo[4.4.0]dec-5-ene (IL-TBD) was synthesized and investigated for its ability to act as an active organocatalyst in the Michael addition of active methylene compounds and thiophenols to chalcones under solven
- Muthyala, Manoj Kumar,Chhikara, Bhupender S.,Parang, Keykavous,Kumar, Anil
-
experimental part
p. 290 - 297
(2012/04/23)
-
- Mesoporous SBA-15 with short mesochannels immobilized natural quinine for asymmetric Michael addition of chalcones
-
A heterogeneous catalyst of natural quinine supported on the mesoporous SBA-15 of short mesochannels was originally synthesized through a simple co-condensation approach for asymmetric organocatalysed Michael addition of malononitrile to chalcones. The ca
- Chen, Qiu,Xin, Cui,Lou, Lan-Lan,Yu, Kai,Ding, Fei,Liu, Shuangxi
-
experimental part
p. 1378 - 1383
(2012/02/01)
-
- Back to natural cinchona alkaloids: Highly enantioselective Michael addition of malononitrile to enones
-
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
-
supporting information; experimental part
p. 3067 - 3071
(2010/04/06)
-
- Michael addition of active methylene compounds to α, β-unsaturated carbonyl compounds under the influence of molecular sieves in dimethyl sulfoxide
-
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
-
experimental part
p. 1204 - 1205
(2009/12/01)
-
- Natural phosphate modified with lithium nitrate: A new efficient catalyst for the construction of carbon-carbon, carbon-sulfur, and carbon-nitrogen bonds
-
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
-
p. 1203 - 1217
(2008/02/02)
-
- Natural phosphate doped with potassium fluoride: Efficient catalyst for the construction of a carbon-carbon bond
-
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
-
p. 275 - 278
(2013/09/04)
-
- Samarium(III) iodide promoted three-component coupling reactions of aldehydes, α-haloketones, and active methylene or methyl compounds
-
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
-
p. 711 - 715
(2007/10/03)
-
- A novel tandem reaction of chalcone with malononitrile or ethylcyanoacetate promoted by samarium (III) iodide and followed by samarium (II) iodide
-
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
-
p. 288 - 290
(2007/10/03)
-
- Asymmetric Michael Additions via SAMP-/RAMP-Hydrazones Enantioselective 1,4-Addition of Methyl Ketones to Knoevenagel Acceptors
-
Asymmetric Michael addition of lithiated methyl ketone SAMP-hydrazones (S)-2 to 2-benzylidenemalonates and -dinitriles 3 followed by oxidative cleavage of the 1,4-adducts (SR)-4 by ozonolysis affords 2-substituted 4-oxo diesters and -dinitriles (R)-5 in good overall yields of 50-82percent and high enantiomeric excesses (ee >/= 95percent).
- Enders, Dieter,Demir, Ayhan S.,Rendenbach, Beatrice E. M.
-
p. 1731 - 1736
(2007/10/02)
-
- CYCLIZATION OF NITRILES. IX. SYNTHESES BASED ON 2-ARYL-3-AROYL-1,1-DICYANOPROPANES
-
2-Aryl-3-aroyl-1,1-dicyanopropanes and 2-aryl-3-aroyl-1-bromo-1,1-dicyanopropanes were synthesized from chalcones and malononitrile and were converted into 4,6-diaryl-2-bromo-3-cyanopyridines and 3-cyano-2(1H)-pyridinethiones.The 2-aryl-3-aroyl-1-bromo-1,1-dicyanopropanes proved convenient intermediates for the production of the corresponding cyclopropanes and other compounds.By their reaction with urea a new method was developed for the production of substituted 3-cyano-2(1H)-pyridinethiones.The 2-bromo-3-cyanopyridines contain a mobile bromine atom readily exchanged for the various nucleophilic residues of alcohols and amines and for iodide, and cyano and thiocyanato groups.The 3-cyano-2(1H)-pyridinethiones were used in the synthesis of 3-aminothienopyridines through the isolated 2-Z-methylthio-3-cyanopyridines.
- Shestopalov, A. M.,Promonenkov, V. K.,Sharanin, Yu. A.,Rodinovskaya, L. A.,Sharanin, S. Yu.
-
p. 1382 - 1401
(2007/10/02)
-
- SYNTHESIS AND SOME REACTIONS OF 3-CYANOPYRIDINE-2-THIONES
-
New method for the synthesis of 3-cyanopyridine-2-thiones by the reaction of δ-keto nitroles with sulfur and by condensation of chalcones or benzylideneacetone with cyanothioacetamide are given.The compounds obtained were used in various reactions for the preparation of alkylated products, disulfides, and condensed heterocycles, viz., thienopyridines and pyridothienopyrimidines.
- Krauze, A. A.,Bomika, Z. A.,Shestopalov, A. M.,Rodinovskaya, L. A.,Pelcher, Yu. E',et al.
-
p. 279 - 284
(2007/10/02)
-