Anton Prokhorov - Academia.edu (original) (raw)

Papers by Anton Prokhorov

Research paper thumbnail of Direct introduction of acetylene moieties into azines by methodology

Tetrahedron Letters, Apr 1, 2009

The N-oxides of azines 1a–g react with lithium and/or potassium acetylides to give the correspond... more The N-oxides of azines 1a–g react with lithium and/or potassium acetylides to give the corresponding ethynylazines 2a–g. Reaction with lithium acetylide requires subsequent acylation of the intermediate anionic adduct for rearomatization whereas in the case of potassium acetylide, auto-aromatization takes place.

Research paper thumbnail of Reactions of triazines and tetrazines with dienophiles (Review)

Chemistry of Heterocyclic Compounds, Nov 1, 2012

Information on the development of a valuable synthetic methodology based on inverse electron-dema... more Information on the development of a valuable synthetic methodology based on inverse electron-demand Diels–Alder reaction in the series of π-deficient azadienes (triazines and tetrazines) is summarized and classified. By this method it is possible to obtain mono-, di-, and triazines containing functional substituents both from the initial azine and from the dienophile. Such reactions are often the simplest and even the only possible method for the synthesis of substances with properties suitable for practical applications.

Research paper thumbnail of The liquid-crystalline and luminescence properties of polycatenar diphenylpyridine complexes of Palladium(II)

Journal of Organometallic Chemistry

Research paper thumbnail of SNH reactions of pyrazine N-oxides and 1,2,4-triazine 4-oxides with CH-active compounds

Russian Chemical Bulletin, 2003

Nucleophilic substitution of hydrogen in pyrazine N-oxides under the action of CH-active compound... more Nucleophilic substitution of hydrogen in pyrazine N-oxides under the action of CH-active compounds requires activation with acylating agents. This activation facilitates aromatization of intermediate σH adducts via elimination of the acid residue to form substituted pyrazines. More electrophilic 1,2,4-triazine 4-oxides react with carbanions derived from CH-active compounds without additional activation according to a scheme, which has previously been unknown for azine N-oxides. This scheme involves aromatization of σH adducts through elimination of water by the E1cb mechanism. The reaction products occur in DMSO-d6 solutions predominantly as 6-methylene-1,6-dihydropyrazines and 5-methylene-4,5-dihydro-1,2,4-triazines.

Research paper thumbnail of Synthesis and mesomorphism of modified 2,5-Di(4-dodecoxyphen-1-yl)-c-cyclopentene-pyridines

Liquid Crystals, 2016

Herein, we report on a new series of mesomorphic compounds synthesised by directional functionali... more Herein, we report on a new series of mesomorphic compounds synthesised by directional functionalisation of 2,5-di(4-dodecoxyphen-1-yl-c-cyclopentene-pyridine) on the c-cyclopentene moiety. The first functionalisation of the starting compound gave rise to a racemic product modified with a hydroxyl group on the fused cyclopentene ring. Further oxidation of this alcohol to a prochiral ketone and subsequent enantioselective reduction back to the alcohol afforded a new chiral alcohol. Further, the hydroxyl group of the chiral alcohol could be substituted by fluorine in a S N 2 reaction, leading to a chiral compound with enantiomeric excess (ee) of 66% and chiral nematic liquid-crystalline (LC) phase.

Research paper thumbnail of Nucleophilic Substitution or Dipolar 1,3-Cycloaddition in Reactions of Cyanamide with 4-Arylpyrimidine 1-Oxides

Research paper thumbnail of Regioselectivity of Nucleophilic Attack in the Reactions of 1,2,4-Triazine 4-Oxides with Certain C-Nucleophiles

ChemInform, 2005

Triazine derivatives R 0655 Regioselectivity of Nucleophilic Attack in the Reactions of 1,2,4-Tri... more Triazine derivatives R 0655 Regioselectivity of Nucleophilic Attack in the Reactions of 1,2,4-Triazine 4-Oxides with Certain C-Nucleophiles.-The reactions of 1,2,4-triazine 4-oxides (I) with C-nucleophiles under conditions of thermodynamic control occurs via nucleophilic attack at the position 3 of the heterocycle [→ (III) and (V)] whilst under conditions of kinetic control the position 5 is attacked [→ (VII)].

Research paper thumbnail of ChemInform Abstract: Reactions of Triazines and Tetrazines with Dienophiles

Research paper thumbnail of V.L. Rusinov, D.N. Kozhevnikov, A.M. Prokhorov, M.M. Ustinova, O.N. Chupakhin, E.V. Novikova, G.P. Belov. Pd-complexes based on bi- and terdantate azaheterocycluc ligands as catalytic systems for alternating copolymerization of ethylene with carbon monoxide. Abstr. of 7-th Intern. Seminar “Scient...

Research paper thumbnail of ChemInform Abstract: Auto-aromatization of the σH-Adducts of 1,2,4-Triazine 4-Oxides with Carbanions in Reactions of Nucleophilic Substitution of Hydrogen

ChemInform, 2001

Auto-aromatization of the σ H-Adducts of 1,2,4-Triazine 4-Oxides with Carbanions in Reactions of ... more Auto-aromatization of the σ H-Adducts of 1,2,4-Triazine 4-Oxides with Carbanions in Reactions of Nucleophilic Substitution of Hydrogen.-Triazine 4-oxides (I) react with stable carbanions to furnish 5-substituted triazines (III) (9 examples) as products of a deoxidative nucleophilic substitution reaction.-(KOZHEVNIKOV, DMITRY N.; PROKHOROV, ANTON M.;

Research paper thumbnail of Triazines and Tetrazines

Progress in Heterocyclic Chemistry, 2014

Abstract This review covers the work published in the calendar year 2013. Novel reaction chemistr... more Abstract This review covers the work published in the calendar year 2013. Novel reaction chemistry and new ring synthetic methods for 1,2,3-triazines, 1,2,4-triazines, 1,3,5-triazines, and tetrazines are reviewed.

Research paper thumbnail of Aromatic Nucleophilic Substitution in 1,2,4-Triazine 4-Oxides with Grignard Reagents

ChemInform, 2004

Addition of the Grignard reagents to 1,2,4-triazine 4-oxides followed by aromatization ofthe inte... more Addition of the Grignard reagents to 1,2,4-triazine 4-oxides followed by aromatization ofthe intermediate σ H -adducts by dehydrogenation or dehydration was used for synthesis of 5-alkyl- or 5-aryl-substituted 1,2,4-triazines and their 4-oxides.

Research paper thumbnail of SHN Reactions of Pyrazine N‐Oxides and 1,2,4‐Triazine 4‐Oxides with CH‐Active Compounds

ChemInform, 2004

Reactions of Pyrazine N-Oxides and 1,2,4-Triazine 4-Oxides with CH-Active Compounds.-The nucleoph... more Reactions of Pyrazine N-Oxides and 1,2,4-Triazine 4-Oxides with CH-Active Compounds.-The nucleophilic substitution of hydrogen in triazine N-oxides (V) with anionic nucleophiles usually proceeds with autoaromatization of the intermediate σ H adducts. Pyrazine N-oxides like (I), however, require activation by acylating agents to undergo this reaction.-(KOZHEVNIKOV, D. N.; KOVALEV, I. S.;

Research paper thumbnail of The amidine rearrangement in 5-amino-6-aryl-1,2,4-triazine-4-oxides initiated by hydroxylamine

Tetrahedron Letters, 2000

Addition of hydroxylamine at the 3 position of 6-aryl-5-amino-1,2,4-triazine-4-oxides initiates t... more Addition of hydroxylamine at the 3 position of 6-aryl-5-amino-1,2,4-triazine-4-oxides initiates the amidine rearrangement resulting in 6-aryl-5-hydroxylamine-1,2,4-triazines, as con®rmed by an experiment with 15 N-labeling.

Research paper thumbnail of The use of the 1,2,4-triazine method of pyridine ligand synthesis for the preparation of a luminescent Pt(II) labeling agent

Tetrahedron Letters, 2012

Research paper thumbnail of Direct introduction of acetylene moieties into azines by methodology

Tetrahedron Letters, 2009

The N-oxides of azines 1a–g react with lithium and/or potassium acetylides to give the correspond... more The N-oxides of azines 1a–g react with lithium and/or potassium acetylides to give the corresponding ethynylazines 2a–g. Reaction with lithium acetylide requires subsequent acylation of the intermediate anionic adduct for rearomatization whereas in the case of potassium acetylide, auto-aromatization takes place.

Research paper thumbnail of Nucleophilic substitution of hydrogen in the reaction of 1,2,4-triazin-4-oxides with cyanamide

Russian Chemical Bulletin, 2000

It was shown that cyanamide can successfully be used in reactions of nucleophilic substitution of... more It was shown that cyanamide can successfully be used in reactions of nucleophilic substitution of hydrogen with 1,2,4-triazin-4-oxides in the presence of a base to give 5-cyanoimino-1,2,4-triazines. It was found by13C NMR spectroscopy that these compounds and their alkylation products at the cyclic nitrogen atom exist in the form of 5-cyanoimino-2,5-dihydro-1,2,4-triazines.

Research paper thumbnail of Auto-aromatization of the σH-adducts of 1,2,4-triazine 4-oxides with carbanions in reactions of nucleophilic substitution of hydrogen

Mendeleev Communications, 2000

Triazine 4-oxides react with stable carbanions to form 5-substituted 1,2,4-triazines as the produ... more Triazine 4-oxides react with stable carbanions to form 5-substituted 1,2,4-triazines as the products of deoxygenation nucleophilic substitution of hydrogen.

Research paper thumbnail of Reactions of triazines and tetrazines with dienophiles (Review)

Chemistry of Heterocyclic Compounds, 2012

Information on the development of a valuable synthetic methodology based on inverse electron-dema... more Information on the development of a valuable synthetic methodology based on inverse electron-demand Diels–Alder reaction in the series of π-deficient azadienes (triazines and tetrazines) is summarized and classified. By this method it is possible to obtain mono-, di-, and triazines containing functional substituents both from the initial azine and from the dienophile. Such reactions are often the simplest and even the only possible method for the synthesis of substances with properties suitable for practical applications.

Research paper thumbnail of Regioselectivity of Nucleophilic Attack on the Reactions of 1,2,4-Triazine 4-Oxides with Certain C-Nucleophiles

Chemistry of Heterocyclic Compounds, 2004

The addition of CH-active compounds to 6-aryl-1,2,4-triazine 4-oxide is reversible and occurs und... more The addition of CH-active compounds to 6-aryl-1,2,4-triazine 4-oxide is reversible and occurs under conditions of kinetic control at position 5 of the heterocycle to form cyclic C(5)-σ H adducts. Under conditions of thermodynamic control the nucleophilic attack is directed to position 3 of the heterocycle and is accompanied by its opening to form the more stable open chain addition products. Attack of ethylmagnesium bromide is directed exclusively to the 5 position of the 6-aryl-1,2,4-triazine 4-oxides as a result of the irreversibility of the given reaction.

Research paper thumbnail of Direct introduction of acetylene moieties into azines by methodology

Tetrahedron Letters, Apr 1, 2009

The N-oxides of azines 1a–g react with lithium and/or potassium acetylides to give the correspond... more The N-oxides of azines 1a–g react with lithium and/or potassium acetylides to give the corresponding ethynylazines 2a–g. Reaction with lithium acetylide requires subsequent acylation of the intermediate anionic adduct for rearomatization whereas in the case of potassium acetylide, auto-aromatization takes place.

Research paper thumbnail of Reactions of triazines and tetrazines with dienophiles (Review)

Chemistry of Heterocyclic Compounds, Nov 1, 2012

Information on the development of a valuable synthetic methodology based on inverse electron-dema... more Information on the development of a valuable synthetic methodology based on inverse electron-demand Diels–Alder reaction in the series of π-deficient azadienes (triazines and tetrazines) is summarized and classified. By this method it is possible to obtain mono-, di-, and triazines containing functional substituents both from the initial azine and from the dienophile. Such reactions are often the simplest and even the only possible method for the synthesis of substances with properties suitable for practical applications.

Research paper thumbnail of The liquid-crystalline and luminescence properties of polycatenar diphenylpyridine complexes of Palladium(II)

Journal of Organometallic Chemistry

Research paper thumbnail of SNH reactions of pyrazine N-oxides and 1,2,4-triazine 4-oxides with CH-active compounds

Russian Chemical Bulletin, 2003

Nucleophilic substitution of hydrogen in pyrazine N-oxides under the action of CH-active compound... more Nucleophilic substitution of hydrogen in pyrazine N-oxides under the action of CH-active compounds requires activation with acylating agents. This activation facilitates aromatization of intermediate σH adducts via elimination of the acid residue to form substituted pyrazines. More electrophilic 1,2,4-triazine 4-oxides react with carbanions derived from CH-active compounds without additional activation according to a scheme, which has previously been unknown for azine N-oxides. This scheme involves aromatization of σH adducts through elimination of water by the E1cb mechanism. The reaction products occur in DMSO-d6 solutions predominantly as 6-methylene-1,6-dihydropyrazines and 5-methylene-4,5-dihydro-1,2,4-triazines.

Research paper thumbnail of Synthesis and mesomorphism of modified 2,5-Di(4-dodecoxyphen-1-yl)-c-cyclopentene-pyridines

Liquid Crystals, 2016

Herein, we report on a new series of mesomorphic compounds synthesised by directional functionali... more Herein, we report on a new series of mesomorphic compounds synthesised by directional functionalisation of 2,5-di(4-dodecoxyphen-1-yl-c-cyclopentene-pyridine) on the c-cyclopentene moiety. The first functionalisation of the starting compound gave rise to a racemic product modified with a hydroxyl group on the fused cyclopentene ring. Further oxidation of this alcohol to a prochiral ketone and subsequent enantioselective reduction back to the alcohol afforded a new chiral alcohol. Further, the hydroxyl group of the chiral alcohol could be substituted by fluorine in a S N 2 reaction, leading to a chiral compound with enantiomeric excess (ee) of 66% and chiral nematic liquid-crystalline (LC) phase.

Research paper thumbnail of Nucleophilic Substitution or Dipolar 1,3-Cycloaddition in Reactions of Cyanamide with 4-Arylpyrimidine 1-Oxides

Research paper thumbnail of Regioselectivity of Nucleophilic Attack in the Reactions of 1,2,4-Triazine 4-Oxides with Certain C-Nucleophiles

ChemInform, 2005

Triazine derivatives R 0655 Regioselectivity of Nucleophilic Attack in the Reactions of 1,2,4-Tri... more Triazine derivatives R 0655 Regioselectivity of Nucleophilic Attack in the Reactions of 1,2,4-Triazine 4-Oxides with Certain C-Nucleophiles.-The reactions of 1,2,4-triazine 4-oxides (I) with C-nucleophiles under conditions of thermodynamic control occurs via nucleophilic attack at the position 3 of the heterocycle [→ (III) and (V)] whilst under conditions of kinetic control the position 5 is attacked [→ (VII)].

Research paper thumbnail of ChemInform Abstract: Reactions of Triazines and Tetrazines with Dienophiles

Research paper thumbnail of V.L. Rusinov, D.N. Kozhevnikov, A.M. Prokhorov, M.M. Ustinova, O.N. Chupakhin, E.V. Novikova, G.P. Belov. Pd-complexes based on bi- and terdantate azaheterocycluc ligands as catalytic systems for alternating copolymerization of ethylene with carbon monoxide. Abstr. of 7-th Intern. Seminar “Scient...

Research paper thumbnail of ChemInform Abstract: Auto-aromatization of the σH-Adducts of 1,2,4-Triazine 4-Oxides with Carbanions in Reactions of Nucleophilic Substitution of Hydrogen

ChemInform, 2001

Auto-aromatization of the σ H-Adducts of 1,2,4-Triazine 4-Oxides with Carbanions in Reactions of ... more Auto-aromatization of the σ H-Adducts of 1,2,4-Triazine 4-Oxides with Carbanions in Reactions of Nucleophilic Substitution of Hydrogen.-Triazine 4-oxides (I) react with stable carbanions to furnish 5-substituted triazines (III) (9 examples) as products of a deoxidative nucleophilic substitution reaction.-(KOZHEVNIKOV, DMITRY N.; PROKHOROV, ANTON M.;

Research paper thumbnail of Triazines and Tetrazines

Progress in Heterocyclic Chemistry, 2014

Abstract This review covers the work published in the calendar year 2013. Novel reaction chemistr... more Abstract This review covers the work published in the calendar year 2013. Novel reaction chemistry and new ring synthetic methods for 1,2,3-triazines, 1,2,4-triazines, 1,3,5-triazines, and tetrazines are reviewed.

Research paper thumbnail of Aromatic Nucleophilic Substitution in 1,2,4-Triazine 4-Oxides with Grignard Reagents

ChemInform, 2004

Addition of the Grignard reagents to 1,2,4-triazine 4-oxides followed by aromatization ofthe inte... more Addition of the Grignard reagents to 1,2,4-triazine 4-oxides followed by aromatization ofthe intermediate σ H -adducts by dehydrogenation or dehydration was used for synthesis of 5-alkyl- or 5-aryl-substituted 1,2,4-triazines and their 4-oxides.

Research paper thumbnail of SHN Reactions of Pyrazine N‐Oxides and 1,2,4‐Triazine 4‐Oxides with CH‐Active Compounds

ChemInform, 2004

Reactions of Pyrazine N-Oxides and 1,2,4-Triazine 4-Oxides with CH-Active Compounds.-The nucleoph... more Reactions of Pyrazine N-Oxides and 1,2,4-Triazine 4-Oxides with CH-Active Compounds.-The nucleophilic substitution of hydrogen in triazine N-oxides (V) with anionic nucleophiles usually proceeds with autoaromatization of the intermediate σ H adducts. Pyrazine N-oxides like (I), however, require activation by acylating agents to undergo this reaction.-(KOZHEVNIKOV, D. N.; KOVALEV, I. S.;

Research paper thumbnail of The amidine rearrangement in 5-amino-6-aryl-1,2,4-triazine-4-oxides initiated by hydroxylamine

Tetrahedron Letters, 2000

Addition of hydroxylamine at the 3 position of 6-aryl-5-amino-1,2,4-triazine-4-oxides initiates t... more Addition of hydroxylamine at the 3 position of 6-aryl-5-amino-1,2,4-triazine-4-oxides initiates the amidine rearrangement resulting in 6-aryl-5-hydroxylamine-1,2,4-triazines, as con®rmed by an experiment with 15 N-labeling.

Research paper thumbnail of The use of the 1,2,4-triazine method of pyridine ligand synthesis for the preparation of a luminescent Pt(II) labeling agent

Tetrahedron Letters, 2012

Research paper thumbnail of Direct introduction of acetylene moieties into azines by methodology

Tetrahedron Letters, 2009

The N-oxides of azines 1a–g react with lithium and/or potassium acetylides to give the correspond... more The N-oxides of azines 1a–g react with lithium and/or potassium acetylides to give the corresponding ethynylazines 2a–g. Reaction with lithium acetylide requires subsequent acylation of the intermediate anionic adduct for rearomatization whereas in the case of potassium acetylide, auto-aromatization takes place.

Research paper thumbnail of Nucleophilic substitution of hydrogen in the reaction of 1,2,4-triazin-4-oxides with cyanamide

Russian Chemical Bulletin, 2000

It was shown that cyanamide can successfully be used in reactions of nucleophilic substitution of... more It was shown that cyanamide can successfully be used in reactions of nucleophilic substitution of hydrogen with 1,2,4-triazin-4-oxides in the presence of a base to give 5-cyanoimino-1,2,4-triazines. It was found by13C NMR spectroscopy that these compounds and their alkylation products at the cyclic nitrogen atom exist in the form of 5-cyanoimino-2,5-dihydro-1,2,4-triazines.

Research paper thumbnail of Auto-aromatization of the σH-adducts of 1,2,4-triazine 4-oxides with carbanions in reactions of nucleophilic substitution of hydrogen

Mendeleev Communications, 2000

Triazine 4-oxides react with stable carbanions to form 5-substituted 1,2,4-triazines as the produ... more Triazine 4-oxides react with stable carbanions to form 5-substituted 1,2,4-triazines as the products of deoxygenation nucleophilic substitution of hydrogen.

Research paper thumbnail of Reactions of triazines and tetrazines with dienophiles (Review)

Chemistry of Heterocyclic Compounds, 2012

Information on the development of a valuable synthetic methodology based on inverse electron-dema... more Information on the development of a valuable synthetic methodology based on inverse electron-demand Diels–Alder reaction in the series of π-deficient azadienes (triazines and tetrazines) is summarized and classified. By this method it is possible to obtain mono-, di-, and triazines containing functional substituents both from the initial azine and from the dienophile. Such reactions are often the simplest and even the only possible method for the synthesis of substances with properties suitable for practical applications.

Research paper thumbnail of Regioselectivity of Nucleophilic Attack on the Reactions of 1,2,4-Triazine 4-Oxides with Certain C-Nucleophiles

Chemistry of Heterocyclic Compounds, 2004

The addition of CH-active compounds to 6-aryl-1,2,4-triazine 4-oxide is reversible and occurs und... more The addition of CH-active compounds to 6-aryl-1,2,4-triazine 4-oxide is reversible and occurs under conditions of kinetic control at position 5 of the heterocycle to form cyclic C(5)-σ H adducts. Under conditions of thermodynamic control the nucleophilic attack is directed to position 3 of the heterocycle and is accompanied by its opening to form the more stable open chain addition products. Attack of ethylmagnesium bromide is directed exclusively to the 5 position of the 6-aryl-1,2,4-triazine 4-oxides as a result of the irreversibility of the given reaction.