Search results for: Vasiliy A. Bakulev

Items from 1 to 20 out of 45 results

article

Design and the synthesis of 1‐heteroaryl‐1,2,3‐triazoles connected to coumarins via ether linker

Muthipeedika Nibin Joy, Nikolai Beliaev, Tetyana V. Beryozkina, Vasiliy A. Bakulev

Journal of Heterocyclic Chemistry > 57 > 8 > 3173 - 3185

In this paper, we report an efficient and versatile methodology for the synthesis of a series of novel heteroaryl‐1,2,3‐triazoles connected to 4‐methylcoumarin (4‐methyl‐2H‐chromen‐2‐one) via oxymethylene linker. The desired molecules were accessed by both two‐step synthesis and the one‐pot copper catalyzed cycloaddition reaction of heteroaromatic azides with coumarin containing acetylenes. The developed...

article

A Base‐Controlled Reaction of 2‐Cyanoacetamidines (3,3‐Diaminoacrylonitriles) with Sulfonyl Azides as a Route to Nonaromatic 4‐Methylene‐1,2,3‐triazole‐5‐imines

Pavel S. Silaichev, Tetyana V. Beryozkina, Mikhail S. Novikov, Wim Dehaen, more

European Journal of Organic Chemistry > 2020 > 24 > 3688 - 3698

Reactions of 2‐cyanoacetamidines with sulfonyl azides were shown to take place via two different pathways to form a mixture of 1‐substituted 5‐amino‐1,2,3‐triazoles 3 and novel 4‐methylene‐1H‐1,2,3‐triazole‐5(4H)‐imine derivatives 4–14. In the absence of a base, 5‐amino‐1,2,3‐triazoles 3 are formed as the only products. The presence of 1.2 equiv. of sodium ethoxide or DBU switches the reaction outcome...

article

[3+2] Anionic Cycloaddition of Isocyanides to Acyclic Enamines and Enaminones: A New, Simple, and Convenient Method for the Synthesis of 2,4‐Disubstituted Pyrroles

Ilya V. Efimov, Maria D. Matveeva, Rafael Luque, Vasiliy A. Bakulev, more

European Journal of Organic Chemistry > 2020 > 9 > 1108 - 1113

We herein demonstrate a new approach for the synthesis of 2,4‐disubstituted pyrroles by [3+2] cycloaddition reaction of isocyanides to the activated double bond of various enamines and enaminones. This process paved the way for the synthesis a series of 2,4‐disubstituted pyrroles, which are known to be intermediates in the synthesis of biologically active compounds, in good to excellent yields from...

article

Synthesis of β-azolyl- and β-azolylcarbonylenamines and their reactions with aromatic azides

Yuri M. Shafran, Tetyana V. Beryozkina, Ilya V. Efimov, Vasiliy A. Bakulev

Chemistry of Heterocyclic Compounds > 2019 > 55 > 8 > 704-715

Synthesis of 4-acetyl-substituted azoles (1,2,3-triazole, 1,2,3-thiadiazole, and 1,2-oxazole) is reported. Organocatalytic reactions of 4-acetyl-1,2,3-triazoles with aryl azides were used to obtain bis-1,2,3-triazoles containing directly linked ring systems. The reactions of 4-acetylazoles with DMF–DMA led to the formation of enamines. It was found that the acetyl and methyl groups in 4-acetyl-5-methyl-1,2,3-thiadiazole...

article

New transformations of N-hetarylcyclopentano[d][1,2,3]triazoline ring into 5-alkoxyvaleramidines

Nikolay A. Belyaev, Tetyana V. Beryozkina, Gert Lubec, Wim Dehaen, more

Chemistry of Heterocyclic Compounds > 2018 > 54 > 11 > 1050-1055

It was found that brief refluxing of N-hetarylcyclopentano[d][1,2,3]triazolines in methanol resulted in the elimination of nitrogen, accompanied by cyclopentane ring opening with the formation of N-hetarylvaleramidines. Amidines containing pyrimidine-2,4-dione ring were synthesized by a one-step procedure – the reaction of 5-azidopyrimidine-2,4-diones with endocyclic enamines containing a cyclopentene...

article

Diastereoselective synthesis of 1,2,3-triazolines fused with pentane and dihydropyran rings

Nikolay A. Belyaev, Tetyana V. Beryozkina, Vasiliy A. Bakulev, Oleg S. Eltsov, more

Chemistry of Heterocyclic Compounds > 2018 > 54 > 10 > 984-988

As a result of studying the reactions of 5-azido-1-methyl-4-nitroimidazole and 2,4,5-trimethoxy-1,3,5-triazine with endocyclic enamines, a diastereoselective method was developed for the synthesis of 1-hetarylcycloalkano[1,2,3]triazolines with cis configuration of substituents at the bridgehead carbon atoms. The structures of the obtained reaction products were studied by methods of NMR spectroscopy,...

article

Synthesis of 1,2,3-triazoles linked into chains with other carbo- and heterocycles by a reaction between β-azolyl enamines and azides

Ilya V. Efimov, Nikolai A. Beliaev, Vasiliy A. Bakulev, Tetyana V. Beryozkina

Chemistry of Heterocyclic Compounds > 2018 > 54 > 2 > 167-172

The reactions of β-azolyl enamines with azides proceeded under solvent-free conditions in the absence of base at 110°С by one of the possible routes, selectively forming 1,4-disubstituted 1,2,3-triazoles. The proposed reaction mechanism includes cycloaddition of the starting reagents, leading to 1,2,3-triazoline intermediates, followed by elimination of dimethylamine and the formation of aromatic...

article

The Rich Chemistry Resulting from the 1,3‐Dipolar Cycloaddition Reactions of Enamines and Azides

Vasiliy A. Bakulev, Tetyana Beryozkina, Joice Thomas, Wim Dehaen

European Journal of Organic Chemistry > 2018 > 3 > 262 - 294

Enamines exhibit exceptionally high reactivity in their 1,3‐dipolar cycloaddition reactions with azides in comparison with other dipolarophiles. This review includes the reactions of various types of enamines with azides of different nature, including catalytic processes. The initial products of the reaction, 1,2,3‐triazolines, are generally unstable and very reactive compounds which are prone to...

article

Reaction of CF3-ynones with azides. An efficient regioselective and metal-free route to 4-trifluoroacetyl-1,2,3-triazoles

Vasiliy M. Muzalevskiy, Mansim N. Mamedzade, Vyacheslav A. Chertkov, Vasiliy A. Bakulev, more

Mendeleev Communications > 2018 > 28 > 1 > 17-19

[3+2] Cycloaddition of CF₃-ynones with azides proceeds regioselectively to give 1-R-4-trifluoroacetyl-1H-1,2,3-triazoles as the major products.

article

Reactions of quinoxalin-2-one with β-diketones: a new approach to 6a,7-dihydro-5H-pyrido[1,2-a]quinoxaline-6,8-diones

Yurii A. Azev, Mikhail I. Kodess, Marina A. Ezhikova, Ol’ga S. Ermakova, more

Mendeleev Communications > 2017 > 27 > 1 > 97-98

Quinoxalin-2-one on heating with acetylacetone, benzoylacetone or heptane-3,5-dione in trifluoroacetic acid gives 6a,7-dihydro-5H-pyrido[1,2-a]quinoxaline-6,8-dione derivatives.

article

Synthesis and (3+2) cycloaddition reactions of N,Nʹ- and C,N-cyclic azomethine imines

Nataliya P. Belskaya, Vasiliy A. Bakulev, Zhijin Fan

Chemistry of Heterocyclic Compounds > 2016 > 52 > 9 > 627-636

This review considers new methods for the synthesis of N,Nʹ- and C,N-cyclic azomethine imines, as well as the most characteristic of their transformations – (3+2)-dipolar cycloaddition reactions. Particular attention was focused on the issues of regio- and stereoselectivity, the effects of the structure of starting materials, solvents, and catalysts on the reaction direction and yields of cycloadducts...

article

Synthesis of Assemblies of Isoxazole and Azoles Based on 1,3-Dipolar Cycloaddition Reaction of Enamines with Nitrile Oxides

Ilya V. Efimov, Yuri M. Shafran, Natalia N. Volkova, Nikolai A. Beliaev, more

Chemistry of Heterocyclic Compounds > 2016 > 52 > 9 > 743-749

2-(1,2,3-Thiadiazol-5-yl)enamines and 3-(1,2,3-triazol-4-yl)enaminones react with arylhydroxamoyl chlorides at room temperature with the exclusive formation of 3-aryl-4-(1,2,3-thiadiazol-5-yl)- and [4-(1,2,3-triazol-4-yl)carbonyl]isoxazoles in high yields. The proposed mechanism includes in situ generation of nitrile oxides, which participate in the (3+2)-dipolar cycloaddition reactions leading to...

article

Multicomponent and domino reactions of 3-aroylacrylic acids in the synthesis of heterocycles

Tetyana V. Beryozkina, Nadezhda N. Kolos, Vasiliy A. Bakulev

Chemistry of Heterocyclic Compounds > 2016 > 52 > 9 > 651-657

This review generalizes the data available on heterocyclizations of 3-aroylacrylic acids and their esters, published over the previous 15 years. Multicomponent, cascade, and domino reactions, as well as cycloaddition and electrocyclization reactions involving 3-aroylacrylic acids and their esters have been used to obtain five- and six-membered aromatic and non-aromatic (including chiral) oxygen- or...

article

Synthesis and biological activity of novel N-(3-furan-2-yl-1-phenyl-1H-pyrazol-5-yl) amides derivatives

Jing-Qian Huo, Liu-Yong Ma, Zhe Zhang, Zhi-Jin Fan, more

Chinese Chemical Letters > 2016 > 27 > 9 > 1547-1550

A series of novel N-(3-furan-2-yl-1-phenyl-1H-pyrazol-5-yl) amides derivatives were designed and synthesized. Their structures were confirmed by ¹H NMR, ¹³C NMR and HRMS. All title compounds were evaluated for their herbicidal and antifungal activities. Preliminary bioassay results indicated that the title compounds showed good to moderate herbicidal activity at 1000mg/L. Compound 6q presented the...

article

Design, Synthesis, and Biological Screening of Novel Anthranilic Diamides

Xuewen Hua, Wutao Mao, Zhijin Fan, Xiaotian Ji, more

Journal of Heterocyclic Chemistry > 53 > 3 > 865 - 875

Three series of new anthranilic diamide derivatives containing sulfide, N‐cyanomethylsulfilimine, and N‐cyanomethylsulfoximine groups were designed and synthesized by combining the active substructures of anthranilic diamides and sulfoxaflor. The structures of all newly synthesized compounds were confirmed by IR and ¹H/¹³C‐NMR, and some of them were confirmed by elemental analysis or HRMS too. The...

article

The new facile and straightforward method for the synthesis of 4H-1,2,3-thiadiazolo[5,4-b]indoles and determination of their antiproliferative activity

Nataliya P. Belskaya, Kseniya I. Lugovik, Vasiliy A. Bakulev, Jenny Bauer, more

European Journal of Medicinal Chemistry > 2016 > 108 > C > 245-257

A series of 4H-1,2,3-thiadiazolo[5,4-b]indoles were synthesized by novel tandem of oxidative cyclization of 3-alkoxycarbonylhydrazonoindoline-2-thiones, 1,5-H-shift and elimination of tert-butoxy(ethoxy)carbonyl group. The simple method for their modifications by the reactions with electrophilic agents were elaborated and as a result of the synthetic investigation a number of N-alkyl-, N-acyl- and...

article

Synthesis of N-heteroarylamidines of 1,2,3-thiadiazole-4-carboxylic acid from 2-cyanothioacetamides and 5-azido-1-methyl-4-nitroimidazole

Nikolay A. Belyaev, Tetyana V. Beryozkina, Vasiliy A. Bakulev

Chemistry of Heterocyclic Compounds > 2016 > 52 > 3 > 206-208

The reaction of 2-cyanothioacetamides with 5-azido-1-methyl-4-nitroimidazole in ethanol in the presence of sodium ethoxide at 0°С lead to the formation of previously unknown N-heteroarylamidines of 1,2,3-thiadiazole-4-carboxylic acid in 58–76% yields.

article

NH-1,2,3-triazoles: synthesis and reactions with electrophilic agents

Vasiliy A. Bakulev, Tetyana A. Beryozkina

Chemistry of Heterocyclic Compounds > 2016 > 52 > 1 > 4-6

Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2016, 52(1), 4–6

article

Reactivity of 1,2,3-triazoles towards sulfonyl chlorides. A novel approach to 1- and 2-sulfonyl-4-azolyl-1,2,3-triazoles

Tetyana V. Beryozkina, Ilya V. Efimov, Walter M.F. Fabian, Nikolai A. Beliaev, more

Tetrahedron > 2015 > 71 > 36 > 6189-6195

The reactions of N-unsubstituted triazoles with sulfonyl chlorides afforded mixtures of regioisomeric 1- and 2-sulfonyl-1,2,3-triazoles. In some cases, pure regioisomers were obtained by crystallization of mixtures of isomers. 1,2,3-Triazoles bearing thiadiazole, isoxazole and benzene rings react with mesyl chloride and tosyl chloride to form mainly 1-substituted 1,2,3-triazoles. Conversely, reactions...

article

1,3-Dipolar cycloaddition of 3-alkylsulfanyl-2-arylazo-3-(tert-cycloalkylamino)acrylonitriles with N-methyl- and N-phenylmaleimides

Nataliya P. Belskaya, Svetlana G. Lesogorova, Julia O. Subbotina, Aleksandr V. Koksharov, more

Tetrahedron > 2015 > 71 > 9 > 1438-1447

A series of 1,2-diaza-1,3-butadienes with terminal S,N-acetal function were obtained and reacted with N-methyl- and N-phenylmaleimides. As a result of the 1,3-dipolar cycloaddition, a range of new functionalized nonaromatic heterocyclic compounds including: octahydro-1H-pyrrolo[3,4-a]indolizine, octahydropyrrolo[3′,4′:3,4]pyrrolo[1,2-a]azepine, hexahydropyrrolo[3′,4′:3,4]pyrrolo[2,1-c][1,4]oxazine...

Publication date

Set your own date range

INFONA - science communication portal

Search results for: Vasiliy A. Bakulev

Design and the synthesis of 1‐heteroaryl‐1,2,3‐triazoles connected to coumarins via ether linker

A Base‐Controlled Reaction of 2‐Cyanoacetamidines (3,3‐Diaminoacrylonitriles) with Sulfonyl Azides as a Route to Nonaromatic 4‐Methylene‐1,2,3‐triazole‐5‐imines

[3+2] Anionic Cycloaddition of Isocyanides to Acyclic Enamines and Enaminones: A New, Simple, and Convenient Method for the Synthesis of 2,4‐Disubstituted Pyrroles

Synthesis of β-azolyl- and β-azolylcarbonylenamines and their reactions with aromatic azides

New transformations of N-hetarylcyclopentano[d][1,2,3]triazoline ring into 5-alkoxyvaleramidines

Diastereoselective synthesis of 1,2,3-triazolines fused with pentane and dihydropyran rings

Synthesis of 1,2,3-triazoles linked into chains with other carbo- and heterocycles by a reaction between β-azolyl enamines and azides

The Rich Chemistry Resulting from the 1,3‐Dipolar Cycloaddition Reactions of Enamines and Azides

Reaction of CF3-ynones with azides. An efficient regioselective and metal-free route to 4-trifluoroacetyl-1,2,3-triazoles

Reactions of quinoxalin-2-one with β-diketones: a new approach to 6a,7-dihydro-5H-pyrido[1,2-a]quinoxaline-6,8-diones

Synthesis and (3+2) cycloaddition reactions of N,Nʹ- and C,N-cyclic azomethine imines

Synthesis of Assemblies of Isoxazole and Azoles Based on 1,3-Dipolar Cycloaddition Reaction of Enamines with Nitrile Oxides

Multicomponent and domino reactions of 3-aroylacrylic acids in the synthesis of heterocycles

Synthesis and biological activity of novel N-(3-furan-2-yl-1-phenyl-1H-pyrazol-5-yl) amides derivatives

Design, Synthesis, and Biological Screening of Novel Anthranilic Diamides

The new facile and straightforward method for the synthesis of 4H-1,2,3-thiadiazolo[5,4-b]indoles and determination of their antiproliferative activity

Synthesis of N-heteroarylamidines of 1,2,3-thiadiazole-4-carboxylic acid from 2-cyanothioacetamides and 5-azido-1-methyl-4-nitroimidazole

NH-1,2,3-triazoles: synthesis and reactions with electrophilic agents

Reactivity of 1,2,3-triazoles towards sulfonyl chlorides. A novel approach to 1- and 2-sulfonyl-4-azolyl-1,2,3-triazoles

1,3-Dipolar cycloaddition of 3-alkylsulfanyl-2-arylazo-3-(tert-cycloalkylamino)acrylonitriles with N-methyl- and N-phenylmaleimides

Filter options

Publication date

Content availability

Keywords

Data set

Journal

INFONA - science communication portal

Search results for: Vasiliy A. Bakulev

Add recipient

Sending message cancelled

Are you sure you want to cancel sending this message?

Send message

Filter options

Publication date

Date range setting

Set the date range to filter the displayed results. You can set a starting date, ending date or both. You can enter the dates manually or choose them from the calendar.

Content availability

Keywords

Data set

Journal

Reporting an error / abuse

Sending the report failed

Accessibility options