Structure of the products of the reaction of 9,10-dimethylacridinium salts with aromatic o-hydroxy aldehydes

The reaction of 9,10-dimethylacridinium methosulfate with aromatic o-hydroxy aldehydes in alcohol in the presence of piperidine gives 10-methyl-4-(10-methyl-9-acridanylidenemethyl)-spiro[acridan-9,2-chromans]. The structure of the compounds obtained was established by means of the PMR, UV, and IR spectra.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 539–544, April, 1973.     

The reactions of 5-aryl-2,3-dimethylisoxazolium salts with aromatic aldehydes

The reactions of the 3-methyl group in 5-aryl-2,3-dimethylisoxazolium tetrafluoroborates with aromatic aldehydes, in the presence of piperidine were studied. Isoxazolium salt reactivity is independent of the phenyl group substituent at C-5 on the isoxazolium salt ring. However, it does depend on the aldehyde structure.     

Successful Baylis-Hillman reaction of acrylamide with aromatic aldehydes.

Acrylamide and aromatic aldehydes were found to undergo the Baylis-Hillman reaction at ambient temperature in an aqueous medium in the presence of a stoichiometric amount of base catalyst, DABCO, to give the corresponding 3-hydroxy-2-methylenepropionamides in 61-99% yield. A faster competing, but reversible, non-Baylis-Hillman reaction was initially observed under the conditions to form N-acylhemiaminals, which later disappeared, as the desired Baylis-Hillman adduct was formed as the major product over an extended period of time (12-48 h). This represents the first demonstration of the Baylis-Hillman reaction of aldehydes with acrylamides, which were thought to be inert under atmospheric pressure and at ambient temperature.     

Highly enantioselective hetero-Diels-Alder reaction of Brassard diene with aromatic aldehydes

[reaction: see text] Hetero-Diels-Alder reactions of Brassard diene with aromatic aldehydes were carried out smoothly in the presence of titanium(IV) tridentate Schiff base complexes to give the corresponding chiral delta-lactones in high enantioselectivities (up to 99% ee) under mild conditions.     

Unusual insertion of product the reaction of 3,3-dichloropenlanedione with aromatic aldehydes

Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, p. 183, January, 1994.     

Titanium catalysis in the Ugi reaction of alpha-amino acids with aromatic aldehydes

[reaction: see text] Ugi reaction between an (S)-alpha-amino acid, an aromatic aldehyde, and an isonitrile proceeds best under catalysis by TiCl(4) in MeOH. The sense of diastereoinduction is (S,S).     

Unexpected cascade transformations in the reaction of aromatic aldehydes with the malononitrile dimer

The one-pot reaction of aromatic aldehydes, malononitrile dimer, and triethylamine unexpectedly led to ammonium salts of not previously assumed 5,7-diamino-4-aryl-2-(dicyanomethyl)-1,4-dihydro-1,8-naphthyridine-3,6-dicarbonitriles, but the isomeric 5,7-diamino-4-aryl-2-(dicyanomethyl)-1,4-dihydro-1,6-naphthyridine-3,8-dicarbonitriles. Following neutralization and dehydrogenation led to the new, annulated with pyridine ring tricyanopyridines (TCPy).     

Albumin-mediated asymmetric nitroaldol reaction of aromatic aldehydes with nitromethane in water

We succeeded in the asymmetric nitroaldol (Henry) reaction of aromatic aldehydes with nitromethane using human serum albumin (HSA) in water at neutral pH. The reaction of 4-nitrobenzaldehyde smoothly proceeded for 24 h at 30 °C to afford the corresponding (R)-2-nitro-1-(4-nitrophenyl)ethanol (27% ee). Lowering the reaction temperature to 0 °C improved the enantioselectivity (53% ee). Although the denatured HSA also catalyzed the coupling reaction, no enantioselectivity was observed. The reaction was also applicable to other substrates bearing various substitutions on the benzene ring, and the ee of (R)-1-(biphenyl-4-yl)-2-nitroethanol was up to 79% ee.     

Chemo-and stereoselectivity of the reaction of aromatic aldehydes with triphenylphosphine and trichloroacetic acid derivatives

Aromatic aldehydes react with triphenylphosphine and ethyl trichloroacetate or trichloroacetonitrile to give the corresponding benzylidene dichlorides or α-chlorocinnamic acid derivatives. The chemo-and regioselectivity of these reactions depend on both the substituent in the aromatic ring and reaction conditions. The product configuration was determined on the basis of the coupling constants ² J _CH and ³ J _CH in the ¹³C NMR spectra.     

Trans stereoselectivity in the reaction of (4-carboxybutylidene)triphenylphosphorane with aromatic aldehydes

Aromatic aldehydes react with $\text{1}$ to give predominantly trans 6-aryl-5-hexenoic acids, under special conditions. A systematic study of the reaction of $\text{1}$ with aldehydes, in a preliminary attempt to define the cause and scope of the trans stereoselectivity, is reported.     

Nickel salt-catalyzed addition reaction of arylboronic acids to aromatic aldehydes

Arylation reaction of aromatic aldehydes with arylboronic acids proceeded smoothly in the presence of a base and catalytic amount of a nickel salt, Ni(ClO₄)₂·6H₂O, in toluene/IPA = 5:1 or IPA to afford corresponding diarylmethanols in good to excellent yields.     

Reaction of 3,3-dichloropentane-2,4-dione with aromatic aldehydes under the conditions of Darzens reaction

3,3-Dichloropentane-2,4-dione reacts with aromatic aldehydes under the conditions of Darzens reaction to give 4-acetoxy-4-aryl-3,3-dichlorobutan-2-ones, the products of insertion into the -C-C bond. The reaction of ethyl dichloroacetylacetate with benzaldehyde yields a derivative of tricyclo[5.1.0.0^3,5]octane, rather than 2,6-bis(1-chlorobenzylidene)cyclohexane-1,4-dione, as the by-product.Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1294–1298, July, 1995.     

Tetronic acid in reaction with aromatic aldehydes and 2-naphthylamine. Investigation of fluorescent and nonlinear-optical characteristics of compounds obtained

By Knoevenagel condensation and by three-component condensation 3-arylmethylenetetrahydrofuran-2,4-diones and previously unknown 8,11-dihydro-11-arylbenzo[f]furo[3,4-b]quinolin-10(7H)-ones were respectively synthesized. The luminescent spectra and nonlinear-optical characteristics of compounds obtained were investigated.     

Competition between cyclisation and bisimine formation in the reaction of 1,3-diaminopropanes with aromatic aldehydes

Condensation of 1,3-diamines with aldehydes or ketones gives rise to two major products, the hexahydropyrimidine and the bisimine. Experimental studies of the reaction between a range of aromatic aldehydes and 1,3-diaminopropane or 1,3-diamino-2-propanol establish that the hexahydropyrimidine is favoured by the less nucleophilic amine and by the presence of electron withdrawing groups on the aryl ring of the aldehyde. Calculations indicate that the electronic nature of this aryl ring substituent influences both the relative thermodynamic stability of the final products and the reactivity of the aldehyde as an electrophile.     

Reaction of perfluoroisobutylene with aromatic aldehydes

Conclusions Depending on the nature of the catalyst, 1,1-bis(trifluoromethyl)-2-arylethylenes or products of the addition of the perfluoro-tert-butyl anion to the carbonyl group are formed in the reaction of perfluoroisobutylene with ArCHO under conditions of nucleophilic catalysis.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 6, pp. 1367–1371, June, 1981.     

Investigation of the products of reaction of epichlorohydrin with aromatic amines

It is shown that the reaction of thionyl chloride with 1, 2, 3, 4-tetrahydro-3-hydroxy-6-methyl[h]benzoquinoline leads not only to aromatization of the tetrahydroquinoline ring, but also to chlorination of the methyl group.For Part II see [3].