Gas-phase cyclisation reactions of 1-(2-arylaminophenyl)alkaniminyl radicals

被引：25

作者：

Leardini, R

McNab, H

Nanni, D

Parsons, S

Reed, D

Tenan, AG

机构：

[1] Univ Edinburgh, Dept Chem, Edinburgh EH9 3JJ, Midlothian, Scotland

[2] Univ Bologna, Dipartimento Chim Organ A Mangini, I-40136 Bologna, Italy

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1998年 / 11期

关键词：

D O I：

10.1039/a800886h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Flash vacuum pyrolysis (FVP) of the oxime ethers 9-11 at 650 degrees C (10(-2)-10(-3) Torr) gives products such as the nitrile 17, carbazoles 19 and 20 and acridines 18 and 21 derived from the corresponding iminyl radicals 13-15. The mechanism proposed for the formation of the acridines involves a key hydrogen abstraction by the iminyl of the adjacent N-H atom. When this route is blocked by an N-methyl group, as in 12, alternative cyclisations ensue, yielding the dihydroquinazoline 26 (via another hydrogen abstraction process) and the benzimidazole 25 (via an iminyl-imidoyl interconversion).

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页码：1833 / 1838

页数：6

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