Utility of N-2-pyridyl-3-oxobutanamide in heterocyclic synthesis: Synthesis of new dihydropyridine, fused pyridine, pyridopyridine, pyridazine and pyridopyrimidinethione derivatives

IF 0.2 4区 化学 Q4 CHEMISTRY, MULTIDISCIPLINARY Afinidad Pub Date : 2008-12-01 DOI:10.21608/ABSB.2008.10502
I. S. A. Hafiz, S. Baker, A. Hussein
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Abstract

2-Aminopyridine was fused with ethyl acetoacetate without solvent for two hours to yield the  N-2-pyridyl–3-oxobutanamide 1. However, when the reaction time was increased to 5 hours a structure 3 was obtained. Condensation of the structure 3 with benzaldehyde gave 4. The reaction of pyridopyridone 3 with arylidenemalononitrile7a-c afforded 4 H-pyran derivative 10a-c. In contrast to the behavior of arylidenemalononitrile 7a-c towards pyridopyridine3, benzylidenemalononitrile 7d reacted withcompound 3 to give a product 11. Compound 1 was allowed to react with arylidenemalononitrile to give the dihydropyridine derivative 17a-d. Alkylation of compound 1 with alkylating agents has been also reported. Thus, compound 1 was condensed with [DMF-DMA] in refluxing dioxane to yield 18, but under the reaction conditions we obtained only 21. The pyridopyridone 3 reacted with benzoylisothiocyanate 25a,b to give thiourea derivatives 26a,b Cyclization of 26a,b in dry dioxane and conc. sulphuric acid afforded pyridopyrimidinethione derivatives 27a,b. On the other hand, coupling of pyridopyridine 3 with the aromatic diazonium salt 28a-e afforded the corresponding azo products 29a-e. Boiling of compound 29 in aqueous solution of HCl afforded the hydrazo products 30. Treatmentof arylhydrazone 30a with malononitrile afforded the pyridazine derivatives 31.
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n -2-吡啶-3-氧丁烷酰胺在杂环合成中的应用:新型二氢吡啶、融合吡啶、吡啶吡啶、吡啶嗪和吡啶嘧啶硫酮衍生物的合成
2-氨基吡啶与乙酰乙酸乙酯无溶剂熔融2小时,得到n -2-吡啶- 3-氧丁酰胺1。然而,当反应时间增加到5小时时,得到了结构3。结构3与苯甲醛缩合得到结构4。吡啶吡啶酮3与芳基乙烯单腈7a-c反应得到4h -吡喃衍生物10a-c。与芳基二乙烯腈7a-c对吡啶的反应相反,苯基二乙烯腈7d与化合物3反应生成产物11。化合物1与芳基二烯腈反应生成二氢吡啶衍生物17a-d。化合物1与烷基化剂的烷基化也有报道。因此,化合物1在回流二氧六烷中与[DMF-DMA]缩合得到18,但在反应条件下我们只得到21。吡啶吡啶酮3与苯甲酰异硫氰酸酯25a,b反应得到硫脲衍生物26a,b 26a,b在干二氧六环和conc中环化。硫酸提供吡啶嘧啶硫酮衍生物27a,b。另一方面,吡啶吡啶3与芳香重氮盐28a-e偶氮结合得到相应的偶氮产物29a-e。化合物29在HCl水溶液中沸腾生成水合产物30。用丙二腈处理芳基腙30a得到吡嗪衍生物31。
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来源期刊
Afinidad
Afinidad 化学-化学综合
CiteScore
0.30
自引率
33.30%
发文量
21
审稿时长
>12 weeks
期刊介绍: Afinidad was founded in 1921 and is the oldest journal in theoretical and applied chemistry published nowadays in Spanish language. Afinidad accepts reviews, original articles and short communications about all aspects of chemical engineering, process engineering, chemistry and biotechnology.
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