Diastereoselective multicomponent synthesis of (4RS,6SR)-4,6-diaryl-5,5-dicyano-2-methyl-1,4,5,6-tetrahydropyridine-3-carboxylates

被引：11

作者：

Vereshchagin, A. N. ^{[1
]}

Karpenko, K. A. ^{[1
]}

Iliyasov, T. M. ^{[1
]}

Elinson, M. N. ^{[1
]}

Dorofeeva, E. O. ^{[1
]}

Fakhrutdinov, A. N. ^{[1
]}

Egorov, M. P. ^{[1
]}

机构：

[1] Russian Acad Sci, ND Zelinsky Inst Organ Chem, 47 Leninsky Prosp, Moscow 119991, Russia

来源：

RUSSIAN CHEMICAL BULLETIN | 2018年 / 67卷 / 11期

基金：

俄罗斯科学基金会;

关键词：

tetrahydropyridines; multicomponent reactions; stereoselectivity; benzylidenemalononitriles; 2-acetyl-3-arylacrylates; ELECTROCATALYTIC TRANSFORMATION; STEREOSELECTIVE-SYNTHESIS; EFFICIENT APPROACH; MALONONITRILE; CYCLOALKYLIDENEMALONONITRILES; 1,4-DIHYDROPYRIDINES; DERIVATIVES; PIPERIDINES; CYCLIZATION; ANTAGONISTS;

D O I：

10.1007/s11172-018-2327-9

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Multicomponent reaction of benzylidenemalononitrile, 2-acetyl-3-arylacrylates, and aqueous ammonia in alcohols at room temperature proceeds stereoselectively to give (4RS,6SR)-4,6-diaryl-5,5-dicyano-2-methyl-1,4,5,6-tetrahydropyridine-3-carboxylates in 55-87% yields. In this reaction, ammonia acts as both the catalyst and the source of nitrogen for constructing tetrahydropyridine cycle.

引用

页码：2049 / 2053

页数：5

共 34 条

[1] L-Proline nitrate: a recyclable and green catalyst for the synthesis of highly functionalized piperidines [J].

Agrawal, Nikita R. ;

Bahekar, Sandeep P. ;

Sarode, Prashant B. ;

Zade, Sanjio S. ;

Chandak, Hemant S. .

RSC ADVANCES, 2015, 5 (58) :47053-47059

[2] Evaluation of anticancer effects of newly synthesized dihydropyridine derivatives in comparison to verapamil and doxorubicin on T47D parental and resistant cell lines in vitro [J].

Bazargan, L. ;

Fouladdel, S. ;

Shafiee, A. ;

Amini, M. ;

Ghaffari, S. M. ;

Azizi, E. .

CELL BIOLOGY AND TOXICOLOGY, 2008, 24 (02) :165-174

[3] 'On-solvent' new domino reaction of salicylaldehyde, malononitrile and 4-hydroxy-6-methylpyridin-2(1H)-one: fast and efficient approach to medicinally relevant 4-pyridinyl-2-amino-4H-chromene scaffold [J].

Elinson, Michail N. ;

Ryzhkov, Fedor V. ;

Vereshchagin, Anatoly N. ;

Korshunov, Alexander D. ;

Novikov, Roman A. ;

Egorov, Mikhail P. .

MENDELEEV COMMUNICATIONS, 2017, 27 (06) :559-561

[4] Multicomponent assembling of isatins, malononitrile and 4-hydroxy-6-methylpyridin-2(1H)-ones: one-pot efficient approach to privileged spiro[indoline-3,4′-pyrano[3,2-c]pyridine]-2,5′(6′H)-dione scaffold [J].

Elinson, Michail N. ;

Ryzhkov, Fedor V. ;

Vereshchagin, Anatoly N. ;

Zaimovskaya, Tatiana A. ;

Korolev, Victor A. ;

Egorov, Mikhail P. .

MENDELEEV COMMUNICATIONS, 2016, 26 (05) :399-401

[5] Unexpected stereoselective sodium acetate catalyzed multicomponent cyclization of aryl aldehydes, malononitrile and acetone into cis-4-dicyanomethylene-2,6-diarylcyclohexane-1,1-dicarbonitriles [J].

Elinson, Michall N. ;

Vereshchagin, Anatolii N. ;

Feducovich, Sergey K. ;

Zaimovskaya, Tatyana A. ;

Starikova, Zoya A. ;

Belyakov, Pavel A. ;

Nikishin, Gennady I. .

TETRAHEDRON LETTERS, 2007, 48 (38) :6614-6619

[6] Electrocatalytic transformation of malononitrile and cycloalkylidenemalononitriles into spirotricyclic and spirotetracyclic compounds containing cyclopropane and pyrroline fragments [J].

M. N. Elinson ;

S. K. Fedukovich ;

T. A. Zaimovskaya ;

A. N. Vereshchagin ;

G. I. Nikishin .

Russian Chemical Bulletin, 2003, 52 (10) :2241-2246

[7] Electrocatalytic transformation of malononitrile and cycloalkylidenemalononitriles into spirobicyclic and spirotricyclic compounds containing 1,1,2,2-tetracyanocyclopropane fragment [J].

Elinson, MN ;

Fedukovich, SK ;

Vereshchagin, AN ;

Dorofeev, AS ;

Dmitriev, DE ;

Nikishin, GI .

RUSSIAN CHEMICAL BULLETIN, 2003, 52 (10) :2235-2240

[8] Dihydropyridine calcium channel antagonists in the management of hypertension [J].

Epstein, Benjamin J. ;

Vogelz, Katherine ;

Palmer, Biff F. .

DRUGS, 2007, 67 (09) :1309-1327

[9] Magnetically recyclable magnetite-ceria (Nanocat-Fe-Ce) nanocatalyst - applications in multicomponent reactions under benign conditions [J].

Gawande, Manoj B. ;

Bonifacio, Vasco D. B. ;

Varma, Rajender S. ;

Nogueira, Isabel D. ;

Bundaleski, Nenad ;

Ghumman, C. Amjad A. ;

Teodoro, Orlando M. N. D. ;

Branco, Paula S. .

GREEN CHEMISTRY, 2013, 15 (05) :1226-1231

[10] 1,4-DIHYDROPYRIDINES - EFFECTS OF CHIRALITY AND CONFORMATION ON THE CALCIUM-ANTAGONIST AND CALCIUM AGONIST ACTIVITIES [J].

GOLDMANN, S ;

STOLTEFUSS, J .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1991, 30 (12) :1559-1578

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