Bondock Samir, Rabie Ramy, Etman Hassan A, Fadda Ahmed A
Department of Chemistry, Faculty of Science, Mansoura University, El-gomhuria Street, ET-35516 Mansoura, Egypt.
Eur J Med Chem. 2008 Oct;43(10):2122-9. doi: 10.1016/j.ejmech.2007.12.009. Epub 2007 Dec 23.
2-cyano-N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)acetamide (1) was utilized as key intermediate for the synthesis of some new coumarin 2, pyridine 3, pyrrole 4, thiazole 7, pyrido[2',3':3,4][pyrazolo[5,1-c]triazine and aminopyrazole 9. Treatment of aminopyrazole 9 with nitrous acid, 1,3-dicarbonyl compounds, enaminone, and DMF-DMA led to the formation of pyrazolo[3,4-d]triazine 10, pyrazolo[1,5-a]pyrimidines 11, 12, 14, and pyrazolo[3,4-d]pyrimidine 13, respectively. Condensation of 9 with isatin afforded Schiff base 16. The newly synthesized compounds were characterized by IR, 1H NMR and mass spectral studies. Representative compounds of the synthesized products were tested and evaluated as antimicrobial agents.
2-氰基-N-(1,5-二甲基-3-氧代-2-苯基-2,3-二氢-1H-吡唑-4-基)乙酰胺(1)被用作合成一些新型香豆素2、吡啶3、吡咯4、噻唑7、吡啶并[2',3':3,4][吡唑并[5,1-c]三嗪和氨基吡唑9的关键中间体。用亚硝酸、1,3-二羰基化合物、烯胺酮和DMF-DMA处理氨基吡唑9分别导致吡唑并[3,4-d]三嗪10、吡唑并[1,5-a]嘧啶11、12、14和吡唑并[3,4-d]嘧啶13的形成。9与异吲哚酮缩合得到席夫碱16。通过红外光谱、1H核磁共振和质谱研究对新合成的化合物进行了表征。对合成产物的代表性化合物作为抗菌剂进行了测试和评估。
