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Synthesis and Crystal Structures of 4,5-Dihydroimidazo[1,5-b]pyrazol-6-ones
SynOpen Pub Date : 2020-10-07 , DOI: 10.1055/s-0040-1707304
Antonio Guirado , María Vera , Bruno Martiz , Francisco Ródenas , José A. Sandoval , Enrique Alarcón , Delia Bautista

The synthesis of previously unattainable 2,5-disubstituted 4,5-dihydroimidazo[1,5-b]pyrazol-6-ones has been developed. Electrochemical reductions of readily available 2,2,2-trichloroethylideneacetophenones were followed by reaction with hydrazine, leading to 3-aryl-5-dichloromethyl-2-pyrazolines. These were treated with isocyanates to obtain the corresponding aminocarbonyl derivatives, which were found to be able to form an otherwise almost inaccessible imidazo[1,5-b]pyrazole ring system via a one-step reaction involving internal condensation followed by hydrogen chloride elimination and aromatization. The molecular­ structures of 2-(4-methylphenyl)-5-tosyl-4,5-dihydro­imidazo[1,5-b]pyrazol-6-one, 5-dichloromethyl-N-(4-chlorophenyl)-4,5-dihydro-3-p-tolylpyrazole-1-carboxamide, and 5-(4-bromophenyl)-2-p-tolyl-4,5-dihydroimidazo[1,5-b]pyrazol-6-one were determined by X-ray crystallographic analysis.



中文翻译:

4,5-二氢咪唑并[1,5-b]吡唑-6-一的合成及晶体结构

已经开发了以前无法获得的2,5-二取代的4,5-二氢咪唑并[1,5 - b ]吡唑-6-酮的合成。电化学还原易得的2,2,2-三氯亚乙基苯乙酮,然后与肼反应,生成3-芳基-5-二氯甲基-2-吡唑啉。将它们用异氰酸酯处理以获得相应的氨基羰基衍生物,发现它们能够通过一步反应(包括内部缩合,然后去除氯化氢和氢键)形成咪唑并[1,5- b ]吡唑环系统。芳香化。2-(4-甲基苯基)-5-甲苯基-4,5-二氢咪唑并[1,5 - b ]吡唑-6-,5-二氯甲基-N的分子结构-(4-氯苯基)-4,5-二氢-3-甲苯基吡唑-1-羧酰胺和5-(4-溴苯基)-2-甲苯基-4,5-二氢咪唑[1,5- b ]通过X射线晶体学分析确定吡唑-6-一。

更新日期:2020-11-03
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