Chemistry Department, Faculty of Science, Princess Nora Bint Abdul Rahman University, Riyadh 11435, Saudi Arabia.
Molecules. 2012 Sep 11;17(9):10902-15. doi: 10.3390/molecules170910902.
The reaction of 4-methyl-2-phenyl-1,2-dihydro-6-oxo-5-pyridine- carbonitrile (1) with arylidene malononitrile afforded isoquinoline derivatives 2a,b. 6-Chloro-4-methyl-2-phenyl-5-pyridinecarbonitile (3) obtained by chlorination of compound 1 with phosphoryl chloride was converted into 6-amino-4-methyl-2-phenyl-5-pyridinecarbonitrile (4) and 6-hydrazido-4-methyl-2-phenyl-5-pyridinecarbonitrile (5) in good yield, through reactions with ammonium acetate and hydrazine hydrate, respectively. Treatment of 4 with ethyl acetoacetate, acetic anhydride, formic acid, urea and thiourea gave the corresponding pyrido [2,3-d] pyrimidine derivatives 7–10a,b. A new series of 6-substituted-4-methyl-2-phenyl-5-pyridine carbonitriles 11–13 has been synthesized via reaction of 4 with phenyl isothiocyanate, benzenesulphonyl chloride and acetic anhydride. Treatment of 4 with malononitrile gave 1,8-naphthyridine derivative 14. The reactivity of hydrazide 5 towards acetic acid, phenylisothiocyanate and methylacrylate to give pyrazolo-[3,4-b]-pyridine derivatives 15–17 was studied. Treatment of 5 with acetic anhydride, phthalic anhydride and carbon disulphide gave pyridine derivatives 18,19 and 1,2,4-triazolo-[3,4-a]-pyridine derivative 20.
4-甲基-2-苯基-1,2-二氢-6-氧代-5-吡啶甲腈（1）与亚苄基丙二腈反应得到异喹啉衍生物 2a,b。用氯化磷氯化化合物 1 得到 6-氯-4-甲基-2-苯基-5-吡啶甲腈（3），它分别与乙酸铵和水合肼反应，高产率转化为 6-氨基-4-甲基-2-苯基-5-吡啶甲腈（4）和 6-肼基-4-甲基-2-苯基-5-吡啶甲腈（5）。4 与乙酰乙酸乙酯、乙酸酐、甲酸、尿素和硫脲反应，分别得到相应的吡啶并[2,3-d]嘧啶衍生物 7-10a,b。通过 4 与苯异硫氰酸酯、苯磺酰氯和乙酸酐的反应，合成了一系列新的 6-取代-4-甲基-2-苯基-5-吡啶甲腈 11-13。4 与丙二腈反应得到 1,8-萘啶衍生物 14。研究了酰肼 5 与乙酸、苯异硫氰酸酯和甲基丙烯酸酯反应生成吡唑并[3,4-b]吡啶衍生物 15-17 的反应性。5 与乙酸酐、邻苯二甲酸酐和二硫化碳反应得到吡啶衍生物 18、19 和 1,2,4-三唑并[3,4-a]吡啶衍生物 20。
