ELECTROCYCLIC AROMATIC-SUBSTITUTION BY NITRILE YLIDES TO GIVE 3H-2-BENZAZEPINES - SUBSTITUENT EFFECTS AND MECHANISM

被引：14

作者：

GROUNDWATER, PW ^{[1
]}

SHARP, JT ^{[1
]}

机构：

[1] UNIV EDINBURGH,DEPT CHEM,W MAINS RD,EDINBURGH EH9 3JJ,MIDLOTHIAN,SCOTLAND

来源：

TETRAHEDRON | 1992年 / 48卷 / 37期

关键词：

ELECTROCYCLIC; NITRILE YLIDE; DIAZO-COMPOUND; BENZAZEPINE;

D O I：

10.1016/S0040-4020(01)80469-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Benzonitrile 3,3-diarylallyl nitrile ylides (16), generated by the base-induced dehydrochlorination of imidoyl chlorides, cyclised by 1,7-ring closure to give 3H-2-benzazepines e.g. (19), in contrast to analogous diazo-compounds (1) which prefer 1,5-electrocyclisation. Asymmetrically placed substituents [R in (16b-e)] favour substitution at the ortho (2') position irrespective of their polar electronic effects. Deuterium labelling studies have shown that the cyclisation step is irreversible for these nitrite ylides in contrast to the analogous diazo-compounds (3) for which it is reversible.

引用

页码：7951 / 7964

页数：14

共 21 条

[1] CARBENIC REACTIONS OF 4-DIAZO-4H-IMIDAZOLE WITH BENZENE-DERIVATIVES [J].

AMICK, TJ ;

SHECHTER, H .

TETRAHEDRON LETTERS, 1986, 27 (08) :901-904

[2]

Coops J, 1940, RECL TRAV CHIM PAY-B, V59, P1109

[3] FACILE SYNTHESIS OF 2-ARYLPYRROLES AND 2-HETEROARYLPYRROLES FROM N-ALLYLCARBOXAMIDES [J].

ENGEL, N ;

STEGLICH, W .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1978, 17 (09) :676-676

[4] STERIC EFFECTS IN CYCLISATION OF DIAZOALKENES - A NEW ROOTE TO 1,2-BENZODIAZEPINES [J].

FINDLAY, RH ;

SHARP, JT ;

THOROGOO.PB .

JOURNAL OF THE CHEMICAL SOCIETY D-CHEMICAL COMMUNICATIONS, 1970, (15) :909-&

[5]

FINDLAY RH, 1975, J CHEM SOC P1, P102

[6] THE CYCLIZATION OF BENZONITRILE 3,3-DIARYLALLYL YLIDES TO GIVE 3H-2-BENZAZEPINES - SUBSTITUENT DIRECTIVE EFFECTS AND MECHANISM [J].

GROUNDWATER, PW ;

SHARP, JT .

TETRAHEDRON LETTERS, 1987, 28 (18) :2069-2072

[7] THE CHEMICAL COMPOSITION OF TECHNICAL DDT [J].

HALLER, HL ;

BARTLETT, PD ;

DRAKE, NL ;

NEWMAN, MS ;

CRISTOL, SJ ;

EAKER, CM ;

HAYES, RA ;

KILMER, GW ;

MAGERLEIN, B ;

MUELLER, GP ;

SCHNEIDER, A ;

WHEATLEY, W .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1945, 67 (09) :1591-1602

[8]

JONES G, 1971, J MED CHEM, V14, P161

[9] IONIZATION OF AN ALPHA HYDROGEN OF ACETONITRILE BY N-BUTYLLITHIUM AND ALKALI AMIDES . CONDENSATIONS WITH KETONES AND ALDEHYDES TO FORM BETA-HYDROXYNITRILES [J].

KAISER, EM ;

HAUSER, CR .

JOURNAL OF ORGANIC CHEMISTRY, 1968, 33 (09) :3402-&

[10] PROTONENRESONANZ-UNTERSUCHUNGEN AN SIEBENGLIEDRIGEN RINGVERBINDUNGEN .I. INTRAMOLEKULARE BEWEGLICHKEIT VON AZEPINEN UND DIAZEPINEN [J].

MANNSCHRECK, A ;

RISSMANN, G ;

VOGTLE, F ;

WILD, D .

CHEMISCHE BERICHTE-RECUEIL, 1967, 100 (01) :335-+

← 1 2 3 →