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Synthesis of benzazepinoisoindolinone and bridged tricyclic isoindolinone derivatives
Tetrahedron ( IF 2.1 ) Pub Date : 2020-06-19 , DOI: 10.1016/j.tet.2020.131341
Xiao-Yu Liu , Xi-Meng Luo , Liang-Fu Tang

N-(2,2-Diethoxyethyl)isoindolin-1-ones were readily obtained via the reaction of o-lithiated aromatic imines with carbon monoxide under mild conditions in gram-scale, and they were double-deprotonated by two equivalents of potassium bis(trimethylsilyl)amide at the 3-position and subsequently reacted with ArCH2Br to give 3,3-dibenzyl-N-(2,2-diethoxyethyl)isoindolin-1-ones. Treatment of 3-benzyl-N-(2,2-diethoxyethyl)isoindolin-1-ones with CF3CO2H or AlCl3 led to an intramolecular cyclization reaction to afford benzazepinoisoindolinones, while bridged tricyclic isoindolinone derivatives were successfully obtained using 3,3-dibenzyl-N-(2,2-diethoxyethyl)isoindolin-1-ones as the substrates. Preliminary in vitro tests for fungicidal activity indicate that some bridged tricyclic isoindolinones exhibit good fungicidal activities.



中文翻译:

苯并氮杂庚烯异吲哚啉酮及其桥联三环异吲哚啉酮衍生物的合成

N-(2,2-二乙氧基乙基)异吲哚啉-1-酮可通过邻位锂化的芳族亚胺与一氧化碳在温和条件下以克级反应制得,并通过两当量的双(在3-位的三甲基甲硅烷基)酰胺,然后与ArCH 2 Br反应,得到3,3-二苄基-N-(2,2-二乙氧基乙基)异吲哚啉-1-酮。3-苄基-治疗ñ -异吲哚啉-1-酮与CF(2,2-二乙氧基乙基)3 CO 2 H或的AlCl 3导致分子内环化反应,得到benzazepinoisoindolinones,而成功地使用3中得到桥接三环异吲哚啉衍生物, 3-二苄基-N-(2,2-二乙氧基乙基)异吲哚啉-1-酮为底物。初步的体外杀真菌活性测试表明,某些桥接的三环异吲哚满酮具有良好的杀真菌活性。

更新日期:2020-07-05
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