Открытый доступ Открытый доступ  Доступ закрыт Доступ предоставлен  Доступ закрыт Только для подписчиков

Том 54, № 4 (2018)

Review

Synthesis of 4-(Hydroxymethyl)dihydroisoindolium Salts and Their Intramolecular Recyclization

Chukhadzhyan E., Gevorgyan H., Shahkhatuni K., Chukhadzhyan E., Ayrapetyan L., Khachatryan A.

Аннотация

The review discusses intramolecular cyclization of ammonium salts containing a 4-hydroxybut-2- yn-1-yl group in combination with various π4-fragments, as well as mechanisms of cyclization and intramolecular recyclization of the resulting 4-(hydroxymethyl)dihydroisoindolium salts and their fused analogs. The process is accompanied by neither ring expansion nor contraction, and a pharmacophoric 1,3-dihydrofuran ring is formed instead of dihydroisoindolium fragment. The effects of electronic and structural factors on the intramolecular cyclization and recyclization processes are considered.

Russian Journal of Organic Chemistry. 2018;54(4):517-525
pages 517-525 views

Design of Postmetallocene Catalytic Systems of Arylimine Type for Olefin Polymerization: XVIII. Synthesis of N-Arylsalicylaldimine Ligands Containing meta-or para-Diallylamino Group and Their Titanium(IV) Complexes

Oleynik I., Oleynik I.

Аннотация

Salicylaldehydes containing a tert-butyl or 2-phenylpropan-2-yl group in the 3-position reacted with N,N-diallyl-p-and -m-phenylenediamines in methanol to give the corresponding Schiff bases which were used as ligands to obtain titanium(IV) complexes with the composition L2TiCl2 by reaction with diisopropoxytitanium dichloride.

Russian Journal of Organic Chemistry. 2018;54(4):537-544
pages 537-544 views

Reaction of Perfluorobenzocyclobutene with Excess Pentafluorobenzene in SbF5

Mezhenkova T., Sinyakov V., Karpov V., Zonov Y., Gatilov Y., Platonov V.

Аннотация

The reaction of perfluorobenzocyclobutene with excess pentafluorobenzene in SbF5, followed by hydrolysis, gave a mixture of perfluoro-1,3,3-triphenyl-1,3-dihydro-2-benzofuran-1-ol, perfluoro-1,1,2-triphenylbenzocyclobuten- 5-one, and perfluoro-4-(2,2-diphenylbenzocyclobuten-1-ylidene)cyclohexa-2,5-dien-1- one. When the reaction mixture was treated for a long time with Olah’s reagent (HF–pyridine), isomeric perfluoro-9,10-diphenyl-1,4-, -1,10-, -2,9-, and -9,10-dihydroanthracenes were formed and were converted to perfluoro-9,10-diphenylanthracene by the action of SbF5.

Russian Journal of Organic Chemistry. 2018;54(4):545-553
pages 545-553 views

Synthesis and Structure of 5-(2-Alkoxy-2-oxoethyl)-1,2-diaryl-4-hydroxy-1H-pyrrole-3-carboxylic Acid Esters

Mukovoz P., Slepukhin P., El’tsov O., Ganebnykh I., Gorbunova A., Peshkov S.

Аннотация

Dialkyl 3,4-dihydroxyhexa-2,4-dienedioates reacted with substituted anilines and aromatic aldehydes or with the corresponding Schiff bases to give 5-(2-alkoxy-2-oxoethyl)-1,2-diaryl-4-hydroxy-1H-pyrrole- 3-carboxylates.

Russian Journal of Organic Chemistry. 2018;54(4):554-563
pages 554-563 views

Reductive Heterocyclization of 2-Cyanobenzophenones by the Action of NaBH4. New Efficient Synthesis of 3-Arylphthalides

Mochalov S., Fedotov A., Trofimova E., Zefirov N.

Аннотация

The reduction of 2-cyclopropylcarbonyl-, 2-(thiophen-2-yl)carbonyl-, and 2-arylcarbonylbenzonitriles with sodium tetrahydridoborate afforded 3-cyclopropyl-, 3-(2-thiophen-2-yl)-, and 3-arylphthalides, respectively, in high yields. Under analogous conditions, 3-cyanobenzophenones were converted to the corresponding 3-cyanobenzhydrols.

Russian Journal of Organic Chemistry. 2018;54(4):568-572
pages 568-572 views

1-Alkoxy-7-hydroxy-1,3-dihydrofuro[3,4-c]pyridinium Salts

Bagautdinova R., Kibardina L., Pudovik M., Pudovik E., Burilov A., Trifonov A., Dobrynin A.

Аннотация

New salt structures have been synthesized from pyridoxal and various organic and inorganic acids.

Russian Journal of Organic Chemistry. 2018;54(4):578-581
pages 578-581 views

Chemistry of Iminofurans: XV. Decyclization of Ethyl 2-[5-Aryl-2-oxofuran-3(2H)-ylideneamino]-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylates by the Action of Secondary Amines

Vasileva A., Vaganov V., Shipilovskikh S., Rubtsov A.

Аннотация

Ethyl 2-[5-aryl-2-oxofuran-3(2H)-ylideneamino]-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylates reacted with secondary amines to give 4-aryl-2-(thiophen-2-yl)-4-oxobutanamides, whereas their reaction with piperazine afforded N,N′-disubstituted piperazine derivatives regardless of the reactant ratio.

Russian Journal of Organic Chemistry. 2018;54(4):582-587
pages 582-587 views

Alternative Synthesis of Isoguvacine and Its N-(2-Aryl-2-hydroxyethyl) Derivatives

Abramyants M., Lomov D., Lyashchuk S., Zaporozhets O.

Аннотация

Isonicotinic acid ethyl ester reacted with substituted phenacyl bromides to give the corresponding quaternary salts which were reduced with sodium tetrahydridoborate to ethyl 1-(2-aryl-2-hydroxyethyl)-1,2,3,6- tetrahydropyridine-4-carboxylates. The presence of an electron-donating substituent in the benzene ring of the latter is a necessary condition for their acid hydrolysis with cleavage of the C–N bond and formation of isoguvacine. Analogous derivatives with electron-withdrawing substituents are not converted to isoguvacine under similar conditions.

Russian Journal of Organic Chemistry. 2018;54(4):593-600
pages 593-600 views

Halocyclization of 1-Allyl-6(7)-methylquinolin-2(1H)-ones

Kim D., Vershinina E., Sharutin V.

Аннотация

Oxidation of 1-allyl-6- and -7-methylquinolinium iodides with potassium hexacyanoferrate(III) gave 1-allyl-6(7)-methylquinolin-2(1H)-ones which reacted with halogens to afford 2-halomethyl-7(8)- methyl-1,2-dihydro[1,3]oxazolo[3,2-a]quinolinium halides.

Russian Journal of Organic Chemistry. 2018;54(4):601-605
pages 601-605 views

Some Transformations of 2-(Chloromethyl)-5,5-dimethyl-5,6-dihydrobenzo[h]quinazolin-4(3H)-one

Markosyan A., Hayrapetyan K., Gabrielyan S., Shirinyan V., Mamyan S., Avakimyan J., Stepanyan G.

Аннотация

The condensation of 1-amino-3,3-dimethyl-3,4-dihydronaphthalene-2-carbonitrile with chloroacetyl chloride afforded chloro-N-(2-cyano-3,3-dimethyl-3,4-dihydronaphthalen-1-yl)acetamide which underwent cyclization to 2-(chloromethyl)-5,5-dimethyl-5,6-dihydrobenzo[h]quinazolin-4(3H)-one. The latter reacted with various nucleophiles (alkali metal alkoxides, piperazine, 2-sulfanylethanol) to give 2-(alkoxymethyl)-, 2-(piperazin-1-ylmethyl)-, and 2-{[(2-hydroxyethyl)sulfanyl]methyl}-5,5-dimethyl-5,6-dihydrobenzo[h]quinazolin- 4(3H)-ones. The condensation of 2-(chloromethyl)benzo[h]quinazoline with 2-thioxo derivatives of quinazoline and benzo[h]quinazolines led to the formation of bis-quinazolines in which 5,5-dimethyl-5,6- dihydrobenzo[h]quinazolin-4(3H)-one fragment is linked to quinazoline or benzo[h]quinazoline system through a CH2S bridge.

Russian Journal of Organic Chemistry. 2018;54(4):606-613
pages 606-613 views

Synthesis of Spiroheterocyclic Oxygen-Containing Tryptanthrin Derivatives

Deryabin P., Moskovkina T., Bukreev A., Andina A., Gerasimenko A.

Аннотация

6-Spiro derivatives of tryptanthrin were synthesized in high yields by reaction of indolo[2,1-b]quinazoline- 6,12-dione with alkanediols. The structure of the spiro dioxolane derivatives was studied in detail by X-ray analysis.

Russian Journal of Organic Chemistry. 2018;54(4):622-625
pages 622-625 views

Article

Alkoxytelluration of Allylbenzene

Musalova M., Musalov M., Udalova S., Khabibulina A., Albanov A., Potapov V., Amosova S.

Аннотация

(2-Alkoxy-3-phenylpropyl)trichlorotellanes were synthesized by regioselective reaction of tellurium tetrachloride with allylbenzene in the system MeOH–CH2Cl2, as well as by nucleophilic substitution of chlorine in trichloro(2-chloro-3-phenylpropyl)tellane in MeOH–CH2Cl2 and EtOH–CHCl3. Allylbenzene reacted with tellurium tetrabromide on heating in methanol or ethanol. The reduction of (2-alkoxy-3-phenylpropyl) trihalotellanes with NaBH4 in H2O–THF gave 1,2-bis(2-alkoxy-3-phenylpropyl)ditellanes.

Russian Journal of Organic Chemistry. 2018;54(4):526-529
pages 526-529 views

Reactions of [(3,5-Di-tert-butyl-4-oxocyclohexa-2,5-dien- 1-ylidene)methyl]phosphonates with Phenols

Gibadullina E., Shaekhov T., Voronina Y., Pudovik M., Burilov A.

Аннотация

Dialkyl [(3,5-di-tert-butyl-4-oxocyclohexa-2,5-dien-1-ylidene)methyl]phosphonates reacted with phenol and benzenediols in the presence of trifluoromethanesulfonic acid to give products of electrophilic substitution in the benzene ring, the corresponding diarylmethylphosphonates or [phenylenebis(arylmethylene)]- diphosphonates. The reaction of diphenyl [(3,5-di-tert-butyl-4-oxocyclohexa-2,5-dien-1-ylidene)methyl]phosphonate with 2-methylbenzene-1,3-diol at a ratio of 1: 1 afforded 3-(3,5-di-tert-butyl-4-hydroxyphenyl)-6-hydroxy-7-methyl-2-phenoxy-2,3-dihydro-1,2λ5-benzoxaphosphol-6-one.

Russian Journal of Organic Chemistry. 2018;54(4):530-536
pages 530-536 views

Three-Component Spiro Heterocyclization of Pyrrolediones with Malononitrile and Cyclic Enols

Sal’nikova T., Dmitriev M., Bushmeleva E., Silaichev P., Maslivets A.

Аннотация

Ethyl 4,5-dioxo-2-phenyl-4,5-dihydro-1H-pyrrole-3-carboxylates reacted with malononitrile and five-membered cyclic enols, indan-1,3-dione and cyclopentane-1,3-dione to give 1-substituted ethyl 2-amino-3- cyano-2′,5-dioxo-5′-phenyl-1′,2′-dihydro-5H-spiro[indeno[1,2-b]pyran-4,3′-pyrrole]-4′-carboxylates and ethyl 2-amino-3-cyano-2′,5-dioxo-5′-phenyl-1′,2′,6,7-tetrahydro-5H-spiro[cyclopenta[b]pyran-4,3′-pyrrole]-4′-carboxylates, respectively.

Russian Journal of Organic Chemistry. 2018;54(4):564-567
pages 564-567 views

Reactions of Ethyl 2-Amino-5-(2-aryl-2-oxoethylidene)- 4-oxo-4,5-dihydrofuran-3-carboxylates and 2-Amino-5-(2-aryl- 2-oxoethylidene)-4-oxo-4,5-dihydrofuran-3-carbonitriles with Alcohols

Ivanov D., Igidov N., Shurov S., Dmitriev M., Chernov I.

Аннотация

Ethyl 2-amino-5-(2-aryl-2-oxoethylidene)-4-oxo-1H-4,5-dihydrofuran-3-carboxylates and 2-amino- 5-(2-aryl-2-oxoethylidene)-4-oxo-1H-4,5-dihydrofuran-3-carbonitriles reacted with alcohols in the presence of a catalytic amount of concentrated aqueous HCl to give the corresponding 5-alkoxy-2-amino-5-(2-aryl-2- oxoethyl)-4-oxo-1H-4,5-dihydrofuran-3-carboxylic acid derivatives. A probable reaction mechanism was proposed on the basis B3LYP/6-311G(d) quantum chemical calculations.

Russian Journal of Organic Chemistry. 2018;54(4):573-577
pages 573-577 views

Synthesis of a New Spiro System: 1-Oxa-7-thia-4-azaspiro[4.5]decane 7,7-Dioxide

Pal’chikov V., Gaponov A., Chabanenko R., Mykolenko S.

Аннотация

Dihydro-2H-1λ6-thiopyran-1,1,3(4H)-trione reacted with N-substituted 2-aminoethanols to give derivatives of a new spiro system, 1-oxa-7λ6-thia-4-azaspiro[4.5]decane-7,7-diones. No spirocyclic product was obtained by the reaction with unsubstituted 2-aminoethanol, but the corresponding enamine was formed as in the reactions with other primary amines.

Russian Journal of Organic Chemistry. 2018;54(4):588-592
pages 588-592 views

Substituted 2-(2-Arylethenyl]pyrimidin-4(3H)-ones: Synthesis and Structure

Harutyunyan A., Panosyan G., Tamazyan R., Aivazyan A., Gukasyan G., Danagulyan G.

Аннотация

5-Substituted 2,6-dimethylpyrimidin-4(3H)-ones were synthesized, and their structure was proved by X-ray analysis. Their reactions with aromatic aldehydes regioselectively afforded (Z)-2-(2-arylethenyl)- pyrimidin-4(3H)-ones whose structure was determined by one- and two-dimensional (NOESY) 1H NMR and X-ray analysis.

Russian Journal of Organic Chemistry. 2018;54(4):614-621
pages 614-621 views

Synthesis of Pyrano[4′,3′:2,3]pyrrolo[1,2-a]quinoxalines by Reaction of Aroylpyrroloquinoxalines with Alkyl Vinyl Ethers

Kasatkina S., Titov M., Stepanova E., Dmitriev M., Maslivets A.

Аннотация

Thermally induced [4 + 2]-cycloaddition of 3-aroylpyrrolo[1,2-a]quinoxaline-1,2,4(5H)-triones with alkyl vinyl ethers afforded mixtures of diastereoisomeric (5S*,6aR*)- and (5R*,6aR*)-5-alkoxy-3-aryl-5,6-dihydropyrano[ 4′,3′: 2,3]pyrrolo[1,2-a]quinoxaline-1,2,7(8H)-triones.

Russian Journal of Organic Chemistry. 2018;54(4):626-632
pages 626-632 views

Synthesis, Structure, and Anti-influenza Activity of 2-(Adamantan-1-yl)-5-aryl-1,3,4-oxadiazoles and 2-(Adamantan-1-yl)-5-aryltetrazoles

Seliverstova D., Suslonov V., Zarubaev V., Trifonov R.

Аннотация

Two series of new adamantyl derivatives of polynitrogen heterocycles, 2-(adamantan-1-yl)-5-aryl- 1,3,4-oxadiazoles and 2-(adamantan-1-yl)-5-aryl-2H-tetrazoles, have been synthesized, and their structure has been determined by NMR spectroscopy, mass spectrometry, and X-ray analysis. Biological studies in vitro have revealed high inhibitory activity of some of the synthesized 2-(adamantan-1-yl)-5-aryl-2H-tetrazoles against H1N1 influenza A viruses in combination with a relatively low selectivity.

Russian Journal of Organic Chemistry. 2018;54(4):633-638
pages 633-638 views

1,2,3-Triazole Derivatives Based on Glycine and Phenylalanine Amides and Triterpene Acids

Khusnutdinova E., Petrova A., Faskhutdinova L., Kukovinets O.

Аннотация

Successive conjugation of betulonic and oleanonic acids first with glycine or L-phenylalanine and then with propargylamine or propargyl alcohol and 1,3-dipolar cycloaddition of β-D-glucopyranosyl azide afforded new polyhybrid triterpenoids in an average yield of 65%. The structure of the isolated compounds was determined by NMR spectroscopy.

Russian Journal of Organic Chemistry. 2018;54(4):639-643
pages 639-643 views

Conformational Analysis of Fluoroethane in Nanotubes

Kuznetsov V.

Аннотация

Conformational analysis of a fluoroethane molecule encapsulated in single-walled carbon nanotubes at the DFT PBE/3ζ level of theory showed that the force field of the nanotube considerably reduces the potential barrier to internal rotation about the C–C bond due to increase of the relative stability of the eclipsed or closely related pseudo-staggered conformer, which in some cases correspond to the energy minima. This is accompanied by shortening of the C–C and C–F bonds and appearance of an electric charge on the encapsulated molecule.

Russian Journal of Organic Chemistry. 2018;54(4):644-651
pages 644-651 views

Short Communications

Synthesis of New 1,1′-Selanediyldi(alkan-2-ols)

Kurkutov E., Potapov V., Amosova S.

Аннотация

A procedure has been developed for the synthesis of 1,1′-selanediyldi(alkan-2-ols) by reaction of selenium dibromide with terminal alkenes and subsequent hydrolysis of the addition products in DMF at room temperature in the absence of a base.

Russian Journal of Organic Chemistry. 2018;54(4):652-653
pages 652-653 views

Methylation of Cycloalkanamines with Dimethyl Carbonate in the Presence of Binder-Free NaY Zeolite

Khusnutdinov R., Shchadneva N., Mayakova Y., Egorova T., Khazipova A., Kutepov B.

Аннотация

N-Methyl- and N,N-dimethylcycloalkanamines were synthesized by reaction of cycloalkanamines with dimethyl carbonate in the presence of NaY zeolite containing no binder. Optimal reactant and catalyst ratios and reaction conditions were found.

Russian Journal of Organic Chemistry. 2018;54(4):654-656
pages 654-656 views

Synthesis of Spiro[benzo[g]chromene-4,3′-pyrroles] by Reaction of Pyrrolediones with Malononitrile and 2-Hydroxynaphthalene-1,4-dione

Sal’nikova T., Dmitriev M., Maslivets A.

Аннотация

One-pot reaction of ethyl 1-R-4,5-dioxo-2-phenyl-4,5-dihydro-1H-pyrrole-3-carboxylates with malononitrile and 2-hydroxynaphthalene-1,4-dione in boiling 1,4-dioxane in the presence of triethylamine afforded ethyl 1′-R-2-amino-3-cyano-2′,5,10-trioxo-5′-phenyl-1′,2′,5,10-tetrahydrospiro[benzo[g]chromene- 4,3′-pyrrole]-4′-carboxylates.

Russian Journal of Organic Chemistry. 2018;54(4):657-658
pages 657-658 views

Three-Step Synthesis of 2-Acetyl-4-methyl-3,4-dihydropyran Oximes from Acetylbenzenes and Acetylene

Tatarinova I., Protsuk N., Ushakov I., Schmidt E., Trofimov B.

Аннотация

2-Acetyl-4-methyl-3,4-dihydropyrans reacted with hydroxylamine in pyridine to give (E)-1-(4-methyl-3,4-dihydro-2H-pyran-2-yl)ethan-1-one oximes in up to 85% yield with high stereoselectivity.

Russian Journal of Organic Chemistry. 2018;54(4):659-661
pages 659-661 views

Condensation of 5-Phenylpent-1-en-4-yn-3-one with Arylhydrazines

Golovanov A., Zatynatskiy E., Odin I., Dorogov M., Vikarchuk A.

Аннотация

The reactions of 5-phenylpent-1-en-4-yn-3-one with phenyl- and 4-methylphenylhydrazines in ethanol at room temperature involved the carbonyl group and terminal double bond and afforded 1-aryl-3- (phenylethynyl)-4,5-dihydro-1H-pyrazoles.

Russian Journal of Organic Chemistry. 2018;54(4):662-663
pages 662-663 views

Acylation of 2,3-Dimethylquinoxaline with 5-Arylfuran-2,3-diones

El’chishcheva N., Konovalova V.

Аннотация

1-Aryl-3,4-dihydroxy-5-(3-methylquinoxalin-2-yl)penta-2,4-dien-1-ones were synthesized by reaction of 5-arylfuran-2,3-diones with 2,3-dimethylquinoxaline.

Russian Journal of Organic Chemistry. 2018;54(4):664-665
pages 664-665 views

Synthesis of 6-Aryl-4-[(3-aryl-1H-pyrazol-5-yl)methylidene]- 4,5-dihydropyridazin-3-ols

Anis’kova T., Stulova E., Egorova A.

Аннотация

The reaction of 5-aryl-3-(chromen-3-ylmethylidene)furan-2(3H)-ones with hydrazine led to the formation of 6-aryl-4-{[3-(2-hydroxyphenyl)-1H-pyrazol-5-yl]methylidene}-4,5-dihydropyridazin-3-ols.

Russian Journal of Organic Chemistry. 2018;54(4):666-667
pages 666-667 views

Mechanochemical Activation of the Reaction of Tetraacetylglycoluril with Some Cyclic Primary Amines. Synthesis of Acetamides

Bakibaev A., Khoang N., Mamontov V.

Аннотация

A new mechanochemical method has been proposed for the synthesis of some acetamides containing a cyclic fragment by reaction of primary cyclic amines with tetraacetylglycoluril.

Russian Journal of Organic Chemistry. 2018;54(4):668-669
pages 668-669 views

Согласие на обработку персональных данных с помощью сервиса «Яндекс.Метрика»

1. Я (далее – «Пользователь» или «Субъект персональных данных»), осуществляя использование сайта https://journals.rcsi.science/ (далее – «Сайт»), подтверждая свою полную дееспособность даю согласие на обработку персональных данных с использованием средств автоматизации Оператору - федеральному государственному бюджетному учреждению «Российский центр научной информации» (РЦНИ), далее – «Оператор», расположенному по адресу: 119991, г. Москва, Ленинский просп., д.32А, со следующими условиями.

2. Категории обрабатываемых данных: файлы «cookies» (куки-файлы). Файлы «cookie» – это небольшой текстовый файл, который веб-сервер может хранить в браузере Пользователя. Данные файлы веб-сервер загружает на устройство Пользователя при посещении им Сайта. При каждом следующем посещении Пользователем Сайта «cookie» файлы отправляются на Сайт Оператора. Данные файлы позволяют Сайту распознавать устройство Пользователя. Содержимое такого файла может как относиться, так и не относиться к персональным данным, в зависимости от того, содержит ли такой файл персональные данные или содержит обезличенные технические данные.

3. Цель обработки персональных данных: анализ пользовательской активности с помощью сервиса «Яндекс.Метрика».

4. Категории субъектов персональных данных: все Пользователи Сайта, которые дали согласие на обработку файлов «cookie».

5. Способы обработки: сбор, запись, систематизация, накопление, хранение, уточнение (обновление, изменение), извлечение, использование, передача (доступ, предоставление), блокирование, удаление, уничтожение персональных данных.

6. Срок обработки и хранения: до получения от Субъекта персональных данных требования о прекращении обработки/отзыва согласия.

7. Способ отзыва: заявление об отзыве в письменном виде путём его направления на адрес электронной почты Оператора: info@rcsi.science или путем письменного обращения по юридическому адресу: 119991, г. Москва, Ленинский просп., д.32А

8. Субъект персональных данных вправе запретить своему оборудованию прием этих данных или ограничить прием этих данных. При отказе от получения таких данных или при ограничении приема данных некоторые функции Сайта могут работать некорректно. Субъект персональных данных обязуется сам настроить свое оборудование таким способом, чтобы оно обеспечивало адекватный его желаниям режим работы и уровень защиты данных файлов «cookie», Оператор не предоставляет технологических и правовых консультаций на темы подобного характера.

9. Порядок уничтожения персональных данных при достижении цели их обработки или при наступлении иных законных оснований определяется Оператором в соответствии с законодательством Российской Федерации.

10. Я согласен/согласна квалифицировать в качестве своей простой электронной подписи под настоящим Согласием и под Политикой обработки персональных данных выполнение мною следующего действия на сайте: https://journals.rcsi.science/ нажатие мною на интерфейсе с текстом: «Сайт использует сервис «Яндекс.Метрика» (который использует файлы «cookie») на элемент с текстом «Принять и продолжить».