An efficient synthetic route to carbocyclic enaminonitriles via Lewis acid catalysed domino-ring-opening-cyclisation (DROC) of donor-acceptor cyclopropanes with malononitrile

被引：41

作者：

Ghorai, Manas K. ^{[1
]}

Talukdar, Ranadeep ^{[1
]}

Tiwari, Deo Prakash ^{[1
]}

机构：

[1] Indian Inst Technol, Dept Chem, Kanpur 208016, Uttar Pradesh, India

来源：

CHEMICAL COMMUNICATIONS | 2013年 / 49卷 / 74期

关键词：

ENANTIOSELECTIVE SYNTHESIS; BETA-ENAMINONITRILES; ACTIVATED AZIRIDINES; 3+2 CYCLOADDITION; HETEROCYCLIC SYNTHESIS; BUILDING-BLOCKS; DERIVATIVES; CONSTRUCTION; ANNULATIONS; INHIBITORS;

D O I：

10.1039/c3cc44533j

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A highly efficient strategy for the synthesis of functionalised carbocyclic enaminonitriles in excellent yields has been described. The reaction utilises Yb(OTf)(3) catalysed C-C bond cleavage and two simultaneous C-C bond formations of donor-acceptor (DA)-cyclopr-opanes with malononitrile anions in a domino fashion.

引用

页码：8205 / 8207

页数：3

共 87 条

[1] Design and synthesis of some new thiophene, thienopyrimidine and thienothiadiazine derivatives of antipyrine as potential antimicrobial agents [J].

Aly, Hala M. ;

Saleh, Nashwa M. ;

Elhady, Heba A. .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2011, 46 (09) :4566-4572

[2] The formation and reactions of imino-com-pounds Part I Condensation of ethyl cyano-acetate with its sodium derivative [J].

Baron, H ;

Remfry, FGP ;

Thorpe, JF .

JOURNAL OF THE CHEMICAL SOCIETY, 1904, 85 :1726-1761

[3] An efficient one-pot synthesis of tethered cyclohexadiene enaminonitriles from methyl-ketones: An effective route to quinazolines [J].

Bench, Bennie J. ;

Suarez, Victor H. ;

Watanabe, Coran M. H. .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2008, 18 (10) :3126-3130

[4] Enaminonitrile in heterocyclic synthesis: Synthesis and antimicrobial evaluation of some new pyrazole, isoxazole and pyrimidine derivatives incorporating a benzothiazole moiety [J].

Bondock, Samir ;

Fadaly, Walid ;

Metwally, Mohamed A. .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2009, 44 (12) :4813-4818

[5] Complexity-Building Annulations of Strained Cycloalkanes and C=O π Bonds [J].

Campbell, Matthew J. ;

Johnson, Jeffrey S. ;

Parsons, Andrew T. ;

Pohlhaus, Patrick D. ;

Sanders, Shanina D. .

JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (19) :6317-6325

[6] Asymmetric Synthesis of (+)-Polyanthellin A [J].

Campbell, Matthew J. ;

Johnson, Jeffrey S. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (30) :10370-+

[7] Heterocycles from cyclopropanes: applications in natural product synthesis [J].

Carson, Cheryl A. ;

Kerr, Michael A. .

CHEMICAL SOCIETY REVIEWS, 2009, 38 (11) :3051-3060

[8] Lewis acid-catalyzed reactions of donor-acceptor cyclopropanes with furan derivatives [J].

Chagarovskiy, Alexey O. ;

Budynina, Ekaterina M. ;

Ivanova, Olga A. ;

Grishin, Yuri K. ;

Trushkov, Igor V. ;

Verteletskii, Pavel V. .

TETRAHEDRON, 2009, 65 (27) :5385-5392

[9] Recent Developments in Enantioselective Metal-Catalyzed Domino Reactions [J].

Clavier, Herve ;

Pellissier, Helene .

ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (18) :3347-3403

[10] Three-membered-ring-based molecular architectures [J].

de Meijere, Armin ;

Kozhushkov, Sergei I. ;

Schill, Heiko .

CHEMICAL REVIEWS, 2006, 106 (12) :4926-4996

← 1 2 3 4 5 6 7 8 9 →