INTRAMOLECULAR DIELS-ALDER REACTIONS OF 1-THIA-3-AZABUTADIENES - ONE-POT SYNTHESIS OF ANNULATED THIAZINES FROM N-(TRIMETHYLSILYL)IMINES AND ISOTHIOCYANATES

被引：19
作者：
BARLUENGA, J
TOMAS, M
BALLESTEROS, A
LOPEZ, LA
机构：
[1] Departamento de Química Organometálica, Facultad de Química, Universidad de Oviedo
来源：
JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 19期
关键词：
D O I：
10.1021/jo00019a040
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The intramolecular [4 + 2] cycloaddition of 1-thia-3-aza dienes is described. Substituted N-(trimethylsilyl)imines 2 derived from aromatic and heteroaromatic aldehydes 1 react with isothiocyanates to form heterodienes 3, which, although not isolated, undergo intramolecular cycloaddition at 90-degrees-C to yield heteropolycyclic compounds 5 and 7. The process was found to be regioselective and stereospecific; the stereochemistry of the cycloadducts arises from an exo transition state.
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页码：5680 / 5684
页数：5
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