Pyrimidine annelated heterocycles -: synthesis and cycloaddition of the first pyrimido[1,4]diazepine N-oxides

被引：9

作者：

Heaney, F ^{[1
]}

Burke, C

Cunningham, D

McArdle, P

机构：

[1] Natl Univ Ireland, Dept Chem, Maynooth, Kildare, Ireland

[2] Natl Univ Ireland, Dept Chem, Galway, Ireland

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 2001年 / 06期

关键词：

D O I：

10.1039/b007163n

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

5-Formyl- and 5-acetyl-4-(alkenylamino)pyrimidines 5 have been prepared as precursors to novel pyrimido[1,4]diazepine N-oxides 3. In addition to cyclisation to the targeted dipoles the substrates 5 have also been observed to form imidazopyrimidines 12 and 39 via an intramolecular Michael addition; additionally 5b has been observed to form the pyrimidoazepinone 42. Aldonitrone 3a cycloadded readily to olefinic dipolarophiles; ketodipole 3b did not share this reactivity. Both dipoles reacted with acetylenic dipolarophiles but the ensuing cycloadducts 37 were unstable; facile ring contraction of their isoxazolopyrimidodiazepine skeletons to the pteridine nucleus is noted. The structure of 37c has been determined by X-ray crystallography.

引用

页码：622 / 632

页数：11

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