Department of Chemistry, Faculty of Science, Alexandria University, Ibrahimia P.O. Box 426, Alexandria 21321, Egypt.
Molecules. 2011 Dec 15;16(12):10387-408. doi: 10.3390/molecules161210387.
The formation of (E)-3-{2-(2,5-diphenylpyrazolo[1,5-c]pyrimidin-7-yl)hydrazono}indolin-2-ones 3 has been achieved by condensation of equimolar amounts of 7-hydrazino-2,5-diphenylpyrazolo[1,5-c]pyrimidine (1) and isatin (or isatin derivatives) 2 at room temperature. The (E)-products could be isomerized into corresponding the (Z)-3 isomers. Reactions of the latter fused heterocyclic hydrazones towards different electro-philic reagents yielded the corresponding 3-substituted derivatives 4-7. Dehydrative cyclisation of the hydrazones 3 using phosphorus oxychloride afforded the 2,5-diphenyl- indolo[2,3-e]pyrazolo[1',5':3",4"]pyrimido[2",1"-c][1,2,4] triazines 13. The polyfused heterocyclic ring system 13 underwent electrophilic substitution reactions at position 4 rather than at position 3. The 3-bromo isomer of 17 was prepared by a sequence of reactions starting from 2,5-diphenylpyrazolo[1,5-c]pyrimidine-7(6H)-thione (11). The orientation of the electrophilic attack was supported by spectroscopic and chemical evidence. Some of the synthesized compounds were found to possess slight to moderate activity against the microorganisms Bacillus subtilis, Micrococcus luteus, Staphylococcus aureus, Escherichia coli and Pseudomonas aeruginosa.
（E）-3-{2-（2,5-二苯基吡唑并[1,5-c]嘧啶-7-基）亚肼基}吲哚啉-2-酮的形成是通过等摩尔量的 7-肼基-2,5-二苯基吡唑并[1,5-c]嘧啶（1）和色酮（或色酮衍生物）2 在室温下缩合得到的。（E）-产物可以异构化为相应的（Z）-3 异构体。后者稠合杂环腙与不同的亲电试剂反应得到相应的 3-取代衍生物 4-7。用三氯氧磷使腙 3 脱水环化得到 2,5-二苯基-吲哚并[2,3-e]吡唑并[1',5':3",4"]嘧啶并[2",1"-c][1,2,4]三嗪 13。稠合杂环体系 13 在 4 位而不是 3 位发生亲电取代反应。通过从 2,5-二苯基吡唑并[1,5-c]嘧啶-7(6H)-硫酮（11）开始的一系列反应制备了 3-溴代异构体 17。亲电攻击的方向得到了光谱和化学证据的支持。一些合成化合物被发现对枯草芽孢杆菌、微球菌、金黄色葡萄球菌、大肠杆菌和铜绿假单胞菌等微生物具有轻微到中等的活性。
