T. V. Shokol

Interaction of 2-(2-azahetaryl)-3-oxo-4-chlorobutane nitriles with esters of aromatic amino acids

The reaction of 2-(2-azahetaryl)-3-oxo-4-chlorobutane nitriles with esters of aromatic acids was studied. A series of 1H,4H-3-(2-azahetaryl)pyrrolo[1,2-a] quinazoline-2,5-diones and 1-aryl-2-amino-3-(2-azahetaryl)-4-(5H)-oxopyrroles was obtained. The reaction of the latter with hydrazine and acetic anhydride was investigated.

SYNTHESIS OF 1-R-2-AMINO-3-2-(BENZ)AZOLYL-4(5H)-KETOPYRROLES

A study has been made of the interaction of 2-[2-(benz)azolyl]3-keto-4-chlorobutanenitriles with primary aliphatic amines. This is a convenient method for the synthesis of 2-amino-3-[2-(benz)azolyl]-4(5H)-ketopyrroles.

Chemoselective Alkylation of 3- and 4-(5-Amino-4-hetaryl-2,3-dihydro-3-oxopyrrol-1-yl)benzoic Acids

Alkylation of 3- and 4-(5-amino-4-hetaryl-2,3-dihydro-3-oxopyrrol-1-yl)benzoic acids with phenacyl bromides or chloroacetanilides in DMF in the presence of triethylamine occurs at the carboxy group with high selectivity and yields the corresponding phenacyl and arylcarbamoylmethyl esters. The initial pyrrolylbenzoic acids were synthesized by reaction of 3- and 4-aminobenzoic acids with 4-chloro-2-hetaryl-3-oxo-butyronitriles.

4H,8H-Pyrano[2,3-f]chromene-4,8-diones as versatile precursors for the synthesis of 6-(1,2-oxazol-5-yl)-2H-chromene-2-ones

An efficient and versatile synthesis of 3-azolyl-6-(1,2-oxazol-5-yl)-2H-chromene-2-ones using a Knoevenagel reaction and subsequent cleavage with hydroxylamine hydrochloride is described.Graphical abstract

Synthesis of 6-alkyl-4-[5-dialkylaminomethyl-4-(4-methyl-1,3-thiazol-2-yl)-1H-pyrazol-3-yl]-1,3-benzenediols

6-Alkyl-2-dialkylaminomethyl-7-hydroxy-3-(4-methyl-1,3-thiazol-2-yl)-4H-chromen-4-ones recyclized into 6-alkyl-4-[5-dialkylaminomethyl-4-(4-methyl-1,3-thiazol-2-yl)-1H-pyrazol-3-yl]-1,3-benzenediols under the influence of hydrazine hydrate.

Synthesis and properties of 6,7,8-substituted 2-(4-oxo-3,4-dihydro-2-quinazolinyl)-acetonitriles

Abstract2-(4-Oxo-3,4-dihydro-2-quinazolinyl)acetonitriles have been obtained by the interaction of α-cyanoethylthioiminoacetate with substituted anthranilic acids. Prototropy became apparent in the series of synthesized compounds. Reactions of the 2-(4-oxo-3,4-dihydro-2-quinazolinyl)acetonitriles have been carried out with (hetero)aromatic aldehydes leading to the formation of 3-aryl-2-(4-oxo-3,4-dihydro-2-quinazolinyl)acrylonitriles.

Synthesis of 2-cyanomethylazaheterocycles

Abstract2-(α-Aryloxyacetyl)cyanomethyl-, 2-(α-1-adamantylacetyl)cyanomethyl-, 2-(α-adamantoyl)cyanometyl-, and 2-(α-1-naphthylacetyl)cyanomethylazaheterocycles have been synthesized by treating 2-cyanomethylazaheterocycles with carboxylic acid chlorides. The 2-cyanomethylbenzimidazoles exist in the enaminoketone form. The biological activity of the synthesized compounds was studied and substances possessing fungicidal activity discovered.

Features of the α-azolyl-2-hydroxy-acetophenones reaction with chloroacetyl chloride

The patent [1] reports the synthesis of 2-chloromethyl-7-hydroxyisoflavones by condensation of -aryl2-hydroxyacetophenones with chloroacetic acid anhydride and subsequent acid hydrolysis of the 7-acyloxy group. In our study of the reactivity of -hetaryl-2-hydroxyacetophenones of type 1 we have shown that chloroacetyl chloride acylation of the derivative with a 5-phenyl-1,3,4-thiadiazol-2-yl substituent gives a 2-chloromethylchromone of type 2 [2], while both the -(2-pyridyl)and -(2-quinolyl) derivatives form the products of subsequent intramolecular cyclization with annelation of indolizine or pyrroloquinoline ring to the chromone ring [3, 4].

Synthesis of 6-alkyl-2-dialkylaminomethyl-7-hydroxy-3-(4-methylthiazol-2-yl)-4H-chromen-4-ones

Amination of 6-alkyl-2-chloromethyl-7-hydroxy-3-(4-methylthiazol-2-yl)-4H-chromen-4-ones by secon-dary cyclic amines gives the corresponding 2-dialkylaminomethyl derivatives.