Functionally Substituted 3-Heterylpyrazoles: IX. 3-Aryl(heteryl)-4-mercapto(thiocyanato,isothiocyanato)methylpyrazoles

By reaction of 3-aryl(heteryl)-4-chloromethylpyrazoles with thiourea and sodium thiocyanate respectively 3-aryl(heteryl)-4-mercaptomethylpyrazoles and 3-aryl(heteryl)-thiocyanatomethylpyrazoles were obtained. The latter were subjected to thermal isomerization into 3-aryl(heteryl)-isothiocyanatomethylpyrazoles.     

Stereoselective oxidative rearrangement of 2-aryl tryptamine derivatives

The oxidation of 2-aryl tryptamines followed by a stereoselective rearrangement provides a versatile strategy for the synthesis of C3-quaternary oxindoles bearing a C3-aryl group. Treatment of optically active 2-aryl hydroxyindolenines with scandium trifluoromethanesulfonate in toluene at 110 degrees C leads to complete and stereoselective isomerization to the corresponding C3-aryl oxindoles which represent versatile intermediates for the synthesis of C3a-aryl hexahydropyrroloindoles.     

4-Functionally Substituted 3-Heterylpyrazoles: IV. 1-Phenyl-3-aryl(heteryl)-5-(4-pyrazolyl)-2-pyrazolines

3-Aryl(heteryl)-4-formylpyrazoles in condensation with methyl aryl(heteryl) ketones afforded 1-aryl(heteryl)-3-[3-aryl(heteryl)-4-pyrazolyl]propenones. The latter reacted with phenylhydrazine yielding 1-phenyl-3-aryl(heteryl)-5-(4-pyrazolyl)-2-pyrazolines.     

New Efficient Synthesis of Methyl Trans-2-Aryl (or Hetaryl)-1-Benzamidocyclopropancarboxylates

Methyl trans-2-aryl(or hetaryl)-1-benzamidocyclopropancarboxylates can be easily obtained by thermal decomposition of trans-4-aryl(or hetaryl)-3-benzamido-3-carbomethoxy-Δ¹-pyrazolines synthesized by 1,3-dipolar cycloaddition of diazomethane with methyl E-3-aryl(or hetaryl)-2-benzamido-2-propenoates.     

Synthesis of heterocyclic compounds. XXXIX. Synthesis of 5-cyano-2-phenyl-4-thioxo-3,4-dihydropyrimidines

The reaction of thiobenzamide with 3-alkoxy-3-aryl(or alkyl)-2-cyanopropenenitriles 1 and sodium 2-propoxide in 2-propanol afforded after acidic treatment 6-aryl(or alkyl)-5-cyano-2-phenyl-4-thioxo-3,4-dihydropyrimidines 3 through formation of the 3-aryl(or alkyl)-2-cyano-3-thiobenzamidopropenenitrile 2 that has been isolated in one case ( 2a , R¹ = Ph).     

Dehydrogenation of 1-aryl(hetaryl)-1,2,3,4-tetrahydro-9<Emphasis Type="Italic">H</Emphasis>-β-carboline-3-carboxylic acids and their esters with dimethyl sulfoxide

Oxidative dehydrogenation of 1-aryl(hetaryl)-1,2,3,4-tetrahydro-9Н-β-carboline-3-carboxylic acids derivatives with dimethyl sulfoxide leads to the formation of 1-aryl(hetaryl)-9Н-β-carbolines. Simultaneously with the dehydrogenation decarboxylation occurs. At the oxidation with dimethyl sulfoxide of methyl 1-aryl (hetaryl)-1,2,3,4-tetrahydro-9Н-β-carboline-3-carboxylicates methyl 1-aryl(hetaryl)-9Н-β-carboline-3-carboxylates formed whose hydrolysis afforded the corresponding 1-aryl(hetaryl)-9Н-β-carboline-3-carboxylic acids.     

Facile synthesis of 3-aryl benzofurans, 3-aryl benzothiophenes, 2-aryl indoles and their dimers

The preparation of 3-aryl benzofuran and benzothiophenes and their dimers at 2-position and, 2-aryl indoles and their 3-position dimers preparation is described.     

Direct oxidative conversion of 3-aryl propionaldehydes to 3-aryl acroleins promoted by SOMO catalysis

A new direct oxidative transformation of 3-aryl propionaldehydes to 3-aryl acroleins promoted by SOMO catalysis has been realized with high efficiency under mild reaction conditions.     

Synthesis of Novel 3-Aryl Isoindolinone Derivatives

A library of novel 3-aryl isoindolinone derivatives with aromatic amino acid derivative fragments was designed and synthesized. Two synthetic routes were employed to construct 3-aryl isoindolinone ring system for different amino acid derivatives.     

An efficient synthesis of 3-aryl-2-aryl(or methyl)sulfanylbenzo[b]thiophenes via cyclization of aryl 2-aryl(or methyl)sulfanylmethylsulfanylphenyl ketones

A convenient method for the preparation of 2-aryl(or methyl)sulfanylbenzo[b]thiophenes has been developed. Thus, aryl 2-aryl(or methyl)sulfanylmethylsulfanylphenyl ketones, easily prepared from readily available aryl 2-sulfanylphenyl ketones or 2-chloro-5-nitrophenyl phenyl ketone, are treated with LDA in 1,2-dimethoxyethane (DME) to give 3-aryl-2-aryl(or methyl)sulfanylmethylsulfanyl-2,3-dihydrobenzo[b]thiophen-3-ols, which in turn were dehydrated with thionyl chloride to afford 3-aryl-2-aryl(or methyl)sulfanylbenzo[b]thiophenes in reasonable overall yields.     

An Improved Synthesis,of 3-Aryl Thigphenes Using Phase-Transfer Co-Catalysts

An efficient and facile synthesis of 3-aryl thiophenes From disodium 2-aryl succinates using phosphorus penta sulphide-red phosphorus under phase transfer co-catalyst is reported in near quantitative yield.     

Synthesis of 7-acetyl-8-aryl(hetaryl)- 6-hydroxy-1,6-dimethyl-3-selenoxo-2,3,5,6,7,8-hexahydroiso-quinoline-4-carbonitriles by the condensation of 2,4-diacetyl-3-aryl(hetaryl)- 5-hydroxy-5-methyl-cyclohexanones with cyanoselenoacetamide

7-Acetyl-8-aryl(hetaryl)-6-hydroxy-1,6-dimethyl-3-selenoxo-2,3,5,6,7,8-hexahydroisoquinoline-4-carbo- nitriles have been obtained by the condensation of 2,4-diacetyl-3-aryl(hetaryl)-5-hydroxy-5-methyl-cyclohexanones with cyanoselenoacetamide.     

Synthesis of some 3-aryl-4-oxothiazolin-2-yl-[3-(2-aryl)indolyl]hydrazories

Several 4-aryl-l-[3-(2-aryl)indolyl]-3-thiosemiearbazones and 3-aryl-4-oxothiazolin-2-yl-[3-(2-aryl)indolyl] hydrazones were synthesized as possible antilertility agents. J. Heterocyclic Chem., 15 , 677 (1978)     

Photo-transformations of 6-chloro-3-propargyloxy-2-aryl-4-oxo-4H-1-benzopyran: 1,4-hydrogen abstraction in propargylethers

1,4-Biradicals generated in the Norrish type-II reactions of 3-propargyloxy-2-arylchromones lead to cyclic products involving the 2-aryl group. The formation and distribution of products varied with the nature of 2-aryl group.     

Mn(OAc)3*2H2O promoted addition of arylboronic acids to quinoxalin-2-ones

A simple method has been developed for the synthesis of 3-aryl quinoxalin-2-one derivatives through an oxidative cross-coupling of arylboronic acids with quinoxalin-2-ones using a readily available oxidant Mn(III) acetate dihydrate. This method provides 3-aryl quinoxalin-2-one scaffolds with a broad substrate scope.     

4-Functionally Substituted 3-Heterylpyrazoles: IV. Benzylamino[3-aryl(heteryl)-4-pyrazolyl]methylphosphonic Acids

Derivatives of N-benzyl[3-aryl(heteryl)-4-pyrazolyl]methanimines react with diethyl phosphite to afford diethyl benzylamino[3-aryl(heteryl)-4-pyrazolyl]-4-methylphosphonates that on hydrolysis with 18% hydrochloric acid yield the corresponding aminophosphonic acids.     

Functionally Substituted 3-Heterylpyrazoles: XI. 3-[3-Aryl(heteryl)pyrazol-4-yl]propenoic and Propanoic acids

3-Aryl(heteryl)-4-formylpyrazoles by condensation with malonic acid furnish 3-[3-aryl(heteryl)- pyrazol-4-yl]propenoic acids that in the presence of Raney nickel are reduced by hydrazine hydrate to 3-[3-aryl(heteryl)pyrazol-4-yl]propanoic acids. The successive conversion of both type acids into the corresponding acyl chlorides, esters, and amides was performed.     

Synthesis and Structure of (2E)-3-Aryl(hetaryl)-2-[5-bromo-4-aryl(hetaryl)-1,3-thiazol-2-yl]acrylonitriles

Russian Journal of General Chemistry - Bromination of (2E)-3-aryl(hetaryl)-2-[4-aryl(hetaryl)-1,3-thiazol-2-yl]acrylonitriles proceeds regioselectively at the C5 atom of the thiazole ring with the...     

First acetylenic derivatives of stable 3-imidazoline nitroxides

The Stephens-Castro reaction of copper(I) salts of 1-aryl(hetaryl)alkynes with 2,2,5,5-tetramethyl-4-[2-(4-iodophenyl)-vinyl]imidazoline-3-oxide-1-ol proved to be a general method for the preparation of 2,2,5,5-tetramethyl-4-[2-(p-aryl(hetaryl)ethynylphenyl)]vinyl-3-imidazoline-3-oxide-1-oxyles.     

Palladium-catalyzed asymmetric benzylation of 3-aryl oxindoles

Herein we report palladium-catalyzed asymmetric benzylic alkylation with 3-aryl oxindoles as prochiral nucleophiles. Proceeding analogously to asymmetric allylic alkylation, asymmetric benzylation occurs in high yield and enantioselectivity for a variety of unprotected 3-aryl oxindoles and benzylic methyl carbonates using chiral bisphosphine ligands. This methodology represents a novel asymmetric carbon-carbon bond formation between a benzyl group and a prochiral nucleophile to generate a quaternary center.