R. V. Tyurin

Ambident chemosensors based on benzo[h]chromen-2-one

Schiff bases derived from 7-hydroxy-4-methyl-2-oxobenzo[h]chromene-8-carbaldehyde in solution exist as equilibrium mixtures of benzoid and quinoid tautomers. The fraction of the quinoid tautomer increases with rise in solvent polarity. The Schiff base containing a benzo-15-crown-5 fragment on the nitrogen atom was shown to be a new ambident chemosensor capable of selectively binding transition metal cations via reaction at the o-hydroxyaldehyde imine fragment and alkaline-earth metals via host-guest interaction with the crown ether moiety. This compound exhibits a pronounced sensor activity toward Mg2+ and Ba2+ ions and is a selective naked-eye fluorescent chemosensor for Cu2+ and Co2+ ions.

Structural studies of 1,3-oxazolidine-containing spiropyrans

New 3’-(4-chlorophenyl)-5’,5’-dimethyl-2’-oxospiro[(2H)-chromene-2,4’-1,3-oxazolidine] was synthesized to study the donor influence of the chlorine atom at the N-phenyl substituent on the structure and photochromic properties of 1,3-oxazolidine-containing spiropyrans. Photochemical properties of synthesized 1,3-oxazolidine derivatives were studied at room temperature in toluene. The X-ray diffraction parameters for the new compound were compared with the data obtained earlier for similar spiropyrans.

Cyclic tautomer of 1,5-diacetyl-4,8-dihydroxynaphthalene and its reaction with hydrazine

Demethylation of 1,5-diacetyl-4,8-dimethoxynaphthalene by the action of anhydrous aluminum chloride gave 6-acetyl-2,5-dihydroxy-2-methylnaphtho[1,8-bc]furan which reacted with hydrazine to produce 3,8-dimethyl-1,2,6,7-tetraazapyrene.

Polynuclear heterocyclic systems based on naphthalene-1,5-diol: I. Reaction of naphthalene-1,5-diol and its derivatives with β-dicarbonyl and α, β-unsaturated carbonyl compounds

Reactions of naphthalene-1,5-diol and its derivatives (5-methoxynaphthalen-1-ol, 2-bromo-5-methoxynaphthalen-1-ol, and 2,6-di-tert-butylnaphthalene-1,5-diol) with ethyl acetoacetate, acetylacetone, and p-methoxycinnamic acid under acidic conditions (HCl, HClO4, CF3CO2H) gave substituted benzo[h]-chromenes, naphtho[1,2-b]pyrylium salts, and 3,4-dihydrobenzo[h]chromenes, respectively. Possible mechanisms were proposed for the observed acid-catalyzed heterocyclizations.

Building up of a peri-Hydroxynaphthoyl Fragment on the Core of 2H-Naphtho[1,8-bc] furan

The reaction of 2-aryl-5-acetoxy-4,8-di-tert-butyl-2H-naphtho[1,8-bc]furan with dichloromethyl ethyl ether in the presence of aluminum chloride gave rise to 6-formyl derivatives of the title heterocyclic system, and at the use of aliphatic acids anhydrides in the presence of perchloric acid 6-acyl derivatives were obtained. The target products with a peri-hydroxycarbonyl group were obtained by the ester group elimination.

A new procedure for fusion of a five-membered ring. Building up of the naphtho[1,8-bc]furan system

Reactions of 2,6-di-tert-butylnaphthalene-1,5-diol with aminals derived from aromatic aldehydes afforded 2-aryl-4,8-di-tert-butyl-2H-naphtho[1,8-bc]furan-5-ols and 2-aryl-4,8-di-tert-butylnaphtho[1,8-bc]-furan-5-ones.

Synthesis of 2-(3,3-Dicyano-2-propenylidene)-4,4,5,5-tetramethyldioxolane and Its Reactions with Hydrazine and Primary Amines

Reactions of 2-(β-ethoxyvinyl)-4,4,5,5-tetramethyl-4,5-dihydro-1,3-dioxol-1-ium salts with cyanomethylene compounds gave the corresponding 2-(2-propenylidene)-1,3-dioxolane derivatives which reacted with hydrazine and primary amines to afford, respectively, 3-(2-hydroxy-1,1,2-trimethylpropoxy)pyrazole and 1-substituted 6-amino-5-cyanopyridin-2(1H)-ones.

Oxidative transformatons of 2-aryl-1,2,3,4,7,8-hexahydroacenaphtho[5,6-bc]azepin-4-ones

Reactions of partial (elimination of H2 from the bimethylene unit) and exhaustive (elimination of 2H2 from the bimethylene unit and the seven-membered heterocycle) dehydrogenation of 2-aryl-1,2,3,4,7,8-hexahydroacenaphtho[5,6-bc]azepin-4-ones were performed. The effect of the electronic structure of initial and dehydrogenated compounds on their spectral characteristics was discussed. New peri-fused heterocyclic systems were obtained.

Specific example of the mannich reaction in the series of 5-acetyl-6-aminoacenaphthene and its derivatives

Reactions of 5-acetyl-6-aminoacenaphthene and 5-acetyl-6-acetylaminoacenaphthene with aromatic aldehydes under conditions of base and acid catalysis gave derivatives of a new peri-fused heterocyclic system, 2,3,7,8-tetrahydroacenaphtho[5,6-bc]azepin-4(1H)-ones.

Synthesis and structure of 2-aryl-4H-acenaphth[5,6-bc]oxepin-4-ones

Oxidation of 2-aryl-7,8-dihydro-4H-acenaphth[5,6-bc]oxepin-4-ones with chloranil led to the formation of 2-aryl-4H-acenaphth[5,6-bc]oxepin-4-ones. Their spectral characteristics were analyzed, and a calculation of the molecular structure of model and real compounds was carried out.