DIHYDROPYRANS FROM 1,4-CYCLOADDITION OF ENAMINES TO ARYLMETHYLENEPYRAZOLONES - POLAR CHARACTER OF THE THERMAL REARRANGEMENT OF THE RESULTING CYCLOADDUCTS

被引：4

作者：

ABDELRAHMAN, M

ABDELGHANY, H

机构：

[1] Chemistry Department, Faculty of Science, Assiut University, Sohag

来源：

SYNTHETIC COMMUNICATIONS | 1991年 / 21卷 / 10-11期

关键词：

D O I：

10.1080/00397919108021047

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The inverse electron demand hetero-Diels-Alder reaction of arylmethylenepyrazolones with enamines results in the selective formation of 3,4-dihydro-2H-pyran derivatives. These cycloadducts under thermodynamic conditions, are transformed via the zwitterion, which can be captured in the presence of tetracyanoethylene (TCE), as the more stable Michael-type adducts. The zwitterion could also be the intermediate for the cyclic adducts.

引用

收藏

页码：1281 / 1291

页数：11

相关论文

共 17 条

[1]

ABDELRAHMAN M, IN PRESS SYNTH COMMU

[2] SYNTHESIS OF 1,3-CYCLOHEXADIENES BY REACTION OF ENAMINES WITH METHYL TRANS-2,4-PENTADIENOATE [J].

BERCHTOLD, GA ;

CIABATTO.J ;

TUNICK, AA .

JOURNAL OF ORGANIC CHEMISTRY, 1965, 30 (11) :3679-+

[3] LUPINEN-ALKALOIDE .35. UBER DIE UMSETZUNG VON DEHYDROCHINOLIZIDIN MIT BUTADIENCARBONSAUREESTER [J].

BOHLMANN, F ;

SCHUMANN, D ;

SCHMIDT, O .

CHEMISCHE BERICHTE-RECUEIL, 1966, 99 (05) :1652-&

[4] VINYLAMINES .9. REACTION OF CYCLOHEXANONE ENAMINES WITH ALPHABETA-UNSATURATED KETONES [J].

COLONNA, FP ;

FATUTTA, S ;

RISALITI, A ;

RUSSO, C .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1970, (17) :2377-&

[5] REACTION OF PIPERIDONEENAMINES WITH METHYL BETA-VINYLACRYLATE . A ROUTE TO QUINOLINES AND ISOQUINOLINES [J].

DANISHEF.S ;

CAVANAUG.R .

JOURNAL OF ORGANIC CHEMISTRY, 1968, 33 (07) :2959-&

[6] REACTION OF ENAMINES WITH ACTIVATED BUTADIENES . A 1-STEP SYNTHESIS OF BENZENES [J].

DANISHEFSKY, S ;

CUNNINGHAM, R .

JOURNAL OF ORGANIC CHEMISTRY, 1965, 30 (11) :3676-+

[7]

DESIMONI G, 1970, ANN CHIM-ROME, V60, P208

[8] HETERODIENE SYNTHESES WITH ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS [J].

DESIMONI, G ;

TACCONI, G .

CHEMICAL REVIEWS, 1975, 75 (06) :651-692

[9] HETERODIENE SYNTHESES .13. STEREOCHEMICAL CONSEQUENCES OF ELECTRONIC AND STERIC INTERACTIONS IN TRANSITION-STATE OF CYCLOADDITION BETWEEN 4-ARYLIDENE-5-PYRAZOLONES AND VINYLETHERS [J].

DESIMONI, G ;

COLOMBO, G ;

RIGHETTI, PP ;

TACCONI, G .

TETRAHEDRON, 1973, 29 (17) :2635-2644

[10]

Desimoni G., 1968, GAZZ CHIM ITAL, V98, P1301