Studies with enamines:: Reactivity of N,N-dimethyl-N-[(E)-2-(4-nitrophenyl)-1-ethenyl]amine towards nitrilimine and aromatic diazonium salts.

被引：23
作者：
Al-Matar, Hamad M.
Riyadh, Sayed M.
Elnagdi, Mohamed H.
机构：
[1] Kuwait Univ, Fac Sci, Dept Chem, Safat 13060, Kuwait
[2] Cairo Univ, Fac Sci, Dept Chem, Giza, Egypt
来源：
JOURNAL OF HETEROCYCLIC CHEMISTRY | 2007年 / 44卷 / 03期
关键词：
D O I：
10.1002/jhet.5570440315
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
In the presence of triethylamine, cycloaddition reaction of enarnine 1 with hydrazonoyl halides 2 followed by dimethylamine elimination was achieved, yielding the corresponding 1, 3,4-trisubstituted pyrazoles 4. Coupling of enamine 1 with aromatic diazonium salts afforded 2-(arylhydrazono)-2-(4-nitrophenyl)acetaldehyde 9 in good yield. Refluxing the phenyl hydrazone 9a with chloroacetone in ethanol in the presence of triethylamine afforded 1,3,5-trisubstituted pyrazole 12a, formed via intermediate 11a. Reaction of 9a with hydroxylamine hydrochloride in ethanol in the presence of anhydrous sodium acetate yielded oxime 13a which was irradiated in a microwave oven in the presence of acetic acid to afford a mixture of 15a and 16a.
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页码：603 / 607
页数：5
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