Pyrazolones as versatile precursors for the synthesis of fused and binary heterocycles
Pyrazolones as versatile precursors for the synthesis of fused and binary heterocycles
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DOI：
10.1081/scc-100104042
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发表时间：
2001-01-01
影响因子：
2.1
通讯作者：
Hamama, WS
中科院分区：
文献类型：
--
作者：
Hamama, WS
带有β-酮酯部分的吡唑啉酮与脂肪族二元官能试剂在乙醇中反应，得到二元环杂环2、6和10。而当使用过量的二元试剂时，得到二吡唑并[3，4-c：3 ′，4 ′-f] [1，2]二氮杂衍生物5.另一方面，当化合物1与水合肼在乙酸中反应时，其提供吡唑并[3，4-B]吡啶衍生物7，其中水合肼充当单官能试剂。此外，根据Knorr合成，1与间茴香胺反应得到α，β-不饱和酮衍生物9，代替预期的喹诺酮衍生物8。此外，用芳香族二元官能试剂处理化合物1得到11和13。最后，化合物11通过其与碳酸铵的反应进行稠合，得到吡唑并[3，4-B]吡啶并[6，5-B]苯并二氮杂卓12。
The reaction of pyrazolone bearing a beta -ketoester moiety with aliphatic dibasic functional reagents in ethanol afforded the binary ring heterocycles 2, 6, and 10. Whereas, when using an excess of the dibasic reagent, the dipyrazolo [3,4-c: 3 ' ,4 ' -f] [1,2]diazepine derivative 5 was, obtained. On the other hand, when compound 1 reacted with hydrazine hydrate in acetic acid, it furnished the pyrazolo[3,4-b]pyridine derivative 7 in which the hydrazine hydrate acts as a monofunctional reagent. Also, the reaction of 1 with m-anisidine according to Knorr synthesis gave the alpha,beta -unsaturated ketone derivative 9 in lieu of the anticipated quinolone derivative 8. Furthermore, treatment of compound 1 with aromatic dibasic functional reagents afforded 11 and 13. Eventually, compound 11 was annelated through its reaction with ammonium carbonate to give pyrazolo[3,4-b]pyrido[6,5-b]benzodiazepin 12.