Anna Listratova

• Peoples' Friendship University of Russia

The review summarizes all synthetic methodologies for the preparation of chromeno[3,2-c]pyridines and chromeno[3,2-c]quinolines. The proposed approaches are systemized based on ways for the construction of the heterocyclic system. The presence of these compounds in nature and their bioactivity are also discussed. Natural products with an annelated...

Here, An efficient approach to obtaining previously unknown furo[2′,3′:2,3]pyrrolo[2,1-a]isoquinoline derivatives from readily available 1-R-1-ethynyl-2-vinylisoquinolines is described. The reaction features a simple procedure, occurs in hexaflouroisopropanol and does not require elevated temperatures. It has been found that the addition of glacial...

An efficient approach to the previously unknown furo[2',3':2,3]pyrrolo[2,1-a]isoquinoline deriv-atives from readily available 1-R-1-ethynyl-2-vinylisoquinolines is described. The reaction fea-tures a simple procedure, occurs in hexaflouroisopropanol and does not require elevated tem-peratures. It has been found that the addition of glacial acetic a...

Under microwave (MW) irradiation at 150 °C in toluene and in the presence of nucleophiles (DMAP, triphenylphosphine and tetrahydrothiophene) 1‐substituted 1‐ethynyl‐2‐vinyldi‐ and tetrahydroisoquinolines undergo [3,3]‐sigmatropic rearrangement providing pyrrolo[2,1‐b][3]benzazepines in good yields. The replacement of toluene with acetonitrile direc...

Transformations of 1-methoxymethylethynyl substituted isoquinolines triggered by terminal alkynes in alcohols were studied and new 3-benzazecine-containing compounds synthesized, such as 6-methoxymethyl-3-benzazecines incorporating an endocyclic C6–C8 allene fragment and the -ylidene derivatives 6-methoxymethylene-3-benzazecines. The reaction mecha...

Pericyclic reactions present a convenient tool for constructing heterocyclic systems. They make possible to obtain quite complex structures in one step with high yields and stereoselectivity. A special position in this series is assigned to the named reactions of [3,3]-sigmatropic transformations, including the aza-Claisen one. This rearrangement l...

Transformations of 2-methyl-1-R-1-phenylethynyl-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazines under the action of electron-deficient alkynes in aprotic and protic solvents were studied. 1-Phenyl-1-phenylethynyl substituted pyrrolopyrazine did not react with alkynes or gave complex reaction mixtures. 1-Alkyl substituted 1-phenylethynyl-1,2,3,4-tetrahydr...

We have elaborated a general and simple microwave‐assisted method for the synthesis of original 8‐ylidene decorated benzazecines. We have shown that under the action of electron‐deficient alkynes in acetic acid the starting benzoannulated azacyclic allenes or 1‐alkyl(benzyl)‐1‐phenylethynyl‐substituted isoquinolines underwent transformations leadin...

Recognized as gentler and more environmentally friendly compared to conventional methods, catalytic electrochemical reactions are a powerful tool for constructing heterocycles. Of special interest is indirect electrolysis, where the use of a redox mediator provides an additional means of reaction control, thus avoiding over‐oxidation and facilitati...

The construction of N-heterocyclic rings represents a very important and fast-developing area of organic synthesis. In this context, electrochemistry has emerged as a mild solution for generating in situ the required electrophilic substrates, bases and nucleophiles derived from low-level and extremely stable reagents, the further application of whi...

The title compound, C20H23FN2O4, is the product of a ring-expansion reaction from a seven-membered fluorinated hexa­hydro­azepine to a nine-membered azonine. The nine-membered azonine ring of the mol­ecule adopts a chair–boat conformation. The C=C and C—N bond lengths [1.366 (3) and 1.407 (3) Å, respectively] indicate the presence of conjugation wi...

This review covers recent advances in synthesis of azocine-containing systems. The most approaches towards azocines are discussed. 1 Introduction 2 Ring-Expansion Reaction 2.1 Ring-Expansion Reaction of Cyclopentane Containing the 1,4-Diketone Moiety with Primary Amines (from 5 to 8) 2.2 Ring-Expansion Reaction of Annulated Tetrahydropyridines unde...

The title compound, C20H24N2O4, is the product of a ring-expansion reaction from a seven-membered hexa­hydro­azepine to a nine-membered azonine. The azonine ring of the mol­ecule adopts a chair–boat conformation. In the crystal, mol­ecules are linked by bifurcated N—H⋯(O,O) hydrogen bonds, generating [010] zigzag chains. The title compound shows in...

2-(Chloromethyl)-5,6,7,8-tetrahydropyrido[4',3':4,5]thieno[2,3-d]pyrimidin-4(3De)-ones reacted with acetylenedicarboxylate ester, methyl propiolate or acetylacetylene, forming mixtures of 2-(chloromethyl)-5,6,7,10-tetrahydropyrimido[5',4':4,5]thieno[3,2-d]azocin-4(3De)-ones and 2'-chloromethyl-6'-methylidene-2,3-dihydro-1De-spiro[pyrido[4,5']thieno...

The regioselectivity of the reaction of 10-substituted benzonaphthyridines with dehydrobenzene strongly depends on the electronic effects of the C-10 substituent furnishing predominantly Stevens rearrangement [cf.

A method for the preparation of 4-amino-substituted tetrahydropyrimido[4,5-d]azocines containing an aromatic pyrimidine fragment has been developed. It was established that tetrahydropyrido[4,3-d]pyri-midines are cleaved by the action of activated alkynes with the formation of 6-vinylpyrimidines.

The regioselectivity of dehydrobenzene reaction with 10-substituted benzo[b][1,6]naphthyridines was found to depend on electronic effects due to the C-10 substituent. Stevens rearrangement of 10-cyano-substituted naphthyridines produced 1-alkyl-2-phenyltetrahydrobenzonaphthyridines. 10-Carbamoyl-substituted naphthyridines underwent Hoffman cleavage...

A study was carried out on the domino transformations of tetrahydrobenzofuro[2,3-c]pyridines and tetrahydrobenzofuro[3,2-c]pyridines by the action of activated alkynes in methanol and acetonitrile. This reaction is a new method for the synthesis of spiro[benzofuropyridines] showing acetylcholinesterase inhibition activity.

It was shown that 2,3,4,5-tetrahydro-1,4-benzoxazepines were cleaved at the N–C(5) bond under the action of activated alkynes in methanol, forming o-(methoxyethyl)- and o-(methoxybenzyl)-phenyl(aminoethyl) ethers. The cleavage rate depended on the electronic effects of the substituents at the C-5 atom. Thiazepine ring expansion in tetrahydro-1,4-be...

The reactivity of some new tetrahydrothienopyridines towards activated alkynes was investigated. A novel cascade cleavage-spiroannulation process, leading to the formation of previously unreported derivatives of 1′H-spiro[1-benzothiophene-3,4′-pyridine] was discovered and studied.Graphical abstract

The reactions of partially hydrogenated indoleefused quinolizines and indolizines with activated alkynes in methanol, acetonitrile, and dichloromethane were studied. The reactions were shown to be accompanied by the cleavage of the bridging C—N bond. Azecino[5,44b]] indole and indolo[3,22e][2]benzazonine derivatives were synthesized. Key words: aze...

Tetrahydropyrido[4′,3′:4,5]thieno[2,3-d]pyrimidines in the presence of activated alkynes were transformed into mixtures of pyrimido[5′,4′:4,5]thieno[3,2-d]azocines and spiro[pyridine-4,5′-thieno[2,3-d]pyrimidines].

It has been established that 2-R-4-oxotetrahydropyrido[4,3-d]pyrimidines, under the action of activated alkynes in methanol, form a mixture of 2-R-4-oxohexahydropyrimido[4,5-d]azocines and products of decomposition of the tetrahydropyridine ring, the 2-R-5-methoxymethyl-4-oxo-6-vinylaminoethyl-pyrimidines. Tetrahydropyrido[3,4-d]pyrimidine, isomeri...

We have been studying the development of new asymmetric two-center catalysis using rare earth alkoxides and bifunctional sugar and related ligands. In The Fourth International Conference on Multi-Component Reactions and Related Chemistry (MCR 2009), new catalytic asymmetric reactions using catalysts 1 and 2 and catalytic asymmetric syntheses of ran...

The first synthesis of tetrahydrochromeno[4,3-d]azocines via an alkyne-induced expansion reaction is described.

It has been established that 2-R-4-oxotetrahydropyrido[4,3-d]pyrimidines, under the action of activated alkynes in methanol, form a mixture of 2-R-4-oxohexahydropyrimido[4,5-d]azocines and products of decomposition of the tetrahydropyridine ring, the 2-R-5-methoxymethyl-4-oxo-6-vinylaminoethyl-pyrimidines. Tetrahydropyrido[3,4-d]pyrimidine, isomeri...

Reactions of the title tetrahydropyrrolo[1,2-a]pyrazines with activated alkynes provides ring-opening products, i.e.

A novel and efficient one-pot synthesis of pyrrolo[1,2-d][1,4]diazocines based on tandem transformation of tetrahydropyrazine ring was elaborated.

We are the first to show that quaternary 7-nitropyrido[1,2-a]benzimidazolium salts are cleaved by hydrazine, phenylhydrazine, and hydroxylamine to form 2-pyrazolinemethyl- and 2-isoxazoline-methyl-6-nitrobenzimidazoles.

A simple one-pot protocol allows the synthesis of the title compounds via a cascade reaction of immonium salts (I) and α-hydroxyaromatic aldehydes.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

A one-pot protocol toward previously unreported derivatives of chromeno[2′,2′:4,5]imidazo[2,1-a]isoquinoline via a cascade reaction of isoquinoline-derived immonium salts and α-hydroxy aromatic aldehydes is elaborated.

The reactions of 6-formyl- and 6-trifluoroacetyl-1-methyl-2-R-tetrahydropyrrolo[l, 2-a]-pyrazines with activated alkynes in methanol and acetonitrile have been studied. Terahydro-pyrrolo[l,2-d][l,4]diazocine derivatives were synthesized at the first time.

Reaction of 5-bromo-2-methyl-8-nitro-1,2,3,4-tetrahydroisoquinoline with activated alkynes affords stable tetrahydropyrrolo[2,1-a]isoquinolin-4-ium ylides. Further reactions of ylide 2 gives access to substituted dihydropyrrolo[2,1-a]isoquinolines in good yields.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

This Letter describes a novel synthetic approach towards imidazo[1,2-a]pyridines via a three-component condensation using trimethylsilyl cyanide (TMSCN) or cyanohydrins as the source of CN− ions and silica-sulfuric acid as the catalyst.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

The reaction of 10-carboxamido tetrahydrobenzo[b][1,6]naphthyridines 1-3 with activated terminal alkynes in DMF/methanol resulted with the formation of hexahydrobenzo[b]pyrido[3,4,5-de]-1,6-naph-thyridines 7-10- representatives of a new heterocyclic system.

A novel and efficient one-pot synthesis of thieno[3,2-d]azocines based on tamden transformation of tetrahydropyridine ring was elaborated.Graphical abstract

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Tetrahydroisoquinolines underwent tandem piperidine ring enlargement in the presence of activated alkynes in acetonitrile or methanol, producing tetrahydrobenzo[d]azocines in high yields. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

The transformations of tetrahydrothieno[3,2-c]-and tetrahydrobenzothieno[2,3-c]pyridines in the reactions with acetylenedicarboxylic ester, alkyl propiolates, and acetylacetylene in alcohols were studied. Tetrahydrobenzothieno[3,2-d]azocines and 2-methoxyethyl-3-vinyl-aminoethylbenzothiophenes were synthesized.

Tetrahydroisoquinolines 3a–e underwent piperidine ring enlargement under the action of activated alkynes, giving benzoazocines 4, 5 and 7–11 in high yields.

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