Quinone imines and aminophenols as precursors of new heterocycles

被引：28

作者：

Abakumov, GA ^{[1
]}

Druzhkov, NO ^{[1
]}

Kurskii, YA ^{[1
]}

Abakumova, LG ^{[1
]}

Shavyrin, AS ^{[1
]}

Fukin, GK ^{[1
]}

Poddel'skii, AI ^{[1
]}

Cherkasov, VK ^{[1
]}

Okhlopkova, LS ^{[1
]}

机构：

[1] Russian Acad Sci, GA Razuvaev Inst Organomet Chem, Nizhnii Novgorod 603950, Russia

来源：

RUSSIAN CHEMICAL BULLETIN | 2005年 / 54卷 / 11期

基金：

俄罗斯基础研究基金会;

关键词：

cyclization; 4H-1,4-benzoxazine; 4aH-phenoxazine; 14,16-dioxa-5,9-diaza-8,15-ethenohexaphene; 1,4]benzoxazino[3,2-b][1,4]benzoxazine; stable radical; X-ray diffraction; NMR; ESR;

D O I：

10.1007/s11172-006-0157-7

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Cyclization of substituted quinone imines and diazabutadiene derivatives of aminophenols affords 4aH-phenoxazine or 4H-1,4-benzoxazine derivatives, which are finally transformed into the following fused heterocycles: the stable 1,4,6,8-tetra(tert-butyl)phenoxazin-10-yl radical and 7a,14a,15a,15b-tetrahydro-14,16-dioxa-5,9-diaza-8,15-ethenohexaphene and 5a,6,11a,12-tetrahydro[1,4]benzoxazino[3,2-b][1,4]benzoxazine derivatives. The influence of the substituents on the pathways of the reactions of intermediate benzoxazines and phenoxazines, such as oxidation, [2+4] dimerization, and the closure of the second ring, was studied. The structures of the fused heterocycles were determined by X-ray diffraction, NMR spectroscopy, and ESR.

引用

页码：2571 / 2577

页数：7

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