[3+2]- versus [4+2]-cycloaddition reactions of 3-methylsulfanyl-2-arylazo-3-(pyrrolidin-1-yl)acrylonitriles with N-substituted maleimides involving pyrrolidine-derived azomethine ylides

被引：14

作者：

Deryabina, TG

Belskaia, NP

Kodess, MI

Dehaen, W

Toppet, S

Bakulev, VA

机构：

[1] Urals State Tech Univ, Lab Technol Organ Synth, Ekaterinburg 620002, Russia

[2] Russian Acad Sci, Ural Branch, I Ya Postovsky Inst Organ Synth, Ekaterinburg 620219, Russia

[3] Katholieke Univ Leuven, Dept Chem, B-3001 Louvain, Belgium

来源：

TETRAHEDRON LETTERS | 2006年 / 47卷 / 11期

基金：

俄罗斯基础研究基金会;

关键词：

cycloaddition; diazadienes; azomethine ylides; maleimides; pyrrolizidines;

D O I：

10.1016/j.tetlet.2005.12.130

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

3-Methylsulfanyl-2-arylazo-3-(pyrrolidin-1-yl)acrylonitriles do not enter into [4+2]-cycloaddition reactions with male-imides to form the expected pyrrolo-pyridazines. Instead the formation of novel pyrrolo-pyridazines of type 4 takes place via a formal [3+2]-cycloaddition of initially formed pyrrolidine-derived azomethine ylides 7. The mechanism leading to the final product is discussed. (c) 2006 Elsevier Ltd. All rights reserved.

引用

收藏

页码：1853 / 1855

页数：3

相关论文

共 10 条

[1] Experimental and theoretical insights regarding the cycloaddition reaction of carbohydrate-based 1,2-diaza-1,3-butadienes and acrylonitrile.: A model case for the behavior of chiral azoalkenes and unsymmetric olefinst [J].

Avalos, M ;

Babiano, R ;

Cintas, P ;

Clemente, FR ;

Gordillo, R ;

Jiménez, JL ;

Palacios, JC .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (07) :2241-2251

[2] New heterocyclic precursors for thermal generation of reactive, electron-rich 1,2-diaza-1 3-butadienes [J].

Boeckman, RK ;

Ge, P ;

Reed, JE .

ORGANIC LETTERS, 2001, 3 (23) :3647-3650

[3] SUBSTITUTED 1,3,3A,4,5,6A-HEXAHYDRO-OXAZOLO[4,5-D]-1,2,3-TRIAZOLES FROM A CYCLOADDITION ON A CARBONYL GROUP - THERMAL RING EXPANSION - A NEW ROUTE TO SUBSTITUTED 1,3,4,5-OXATRIAZENES [J].

BUTLER, RN ;

EVANS, AM ;

MCARDLE, P ;

CUNNINGHAM, D .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (14) :1090-1091

[4] The use of 2-azadienes in the Diels-Alder reaction [J].

Gilchrist, TL ;

Gonsalves, AMDR ;

Melo, TMVDPE .

PURE AND APPLIED CHEMISTRY, 1996, 68 (04) :859-862

[5] Diastereoselective cycloadditions of new trifluoromethyl azomethine ylides derived from trifluorothioacetamides [J].

Laduron, F ;

Ates, C ;

Viehe, HG .

TETRAHEDRON LETTERS, 1996, 37 (31) :5515-5518

[6] Diastereoselective 1,3-dipolar cycloadditions of new azomethine ylides derived from trifluorothioacetamides or cyanothioformamides [J].

Laduron, F ;

Viehe, HG .

TETRAHEDRON, 2002, 58 (18) :3543-3551

[7] Cycloaddition reactions of phosphorylated 1,2-diaza-1,3-butadienes with olefins:: Regioselective synthesis of pyridazine derivatives [J].

Palacios, F ;

Aparicio, D ;

López, Y ;

Santos, JMD ;

Alonso, C .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (06) :1142-1147

[8] SYNTHESIS OF BETA-LACTAMS VIA CYCLOADDITION OF HYDRAZONES WITH PHENOXYKETENE [J].

SHARMA, SD ;

PANDHI, SB .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (07) :2196-2200

[9] Synthesis and reactions of haloazodienes. A new and general synthesis of substituted pyridazines [J].

South, MS ;

Jakuboski, TL ;

Westmeyer, MD ;

Dukesherer, DR .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (25) :8921-8934

[10] Novel cyclization reactions of mono- and dichloroazodienes. A new synthesis of substituted pyridazines [J].

South, MS .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1999, 36 (02) :301-319