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A domino approach to pyrazino- indoles and pyrroles using vinyl selenones
Tetrahedron ( IF 2.1 ) Pub Date : 2018-10-26 , DOI: 10.1016/j.tet.2018.10.044
Martina Palomba , Luca Sancineto , Francesca Marini , Claudio Santi , Luana Bagnoli

Herein we disclose an efficient and flexible approach to biologically relevant 3,4-dihydropyrazino[1,2-a]indol-1(2H)ones and 3,4-dihydropyrrolo[1,2-a]pyrazin-1(2H)ones through a domino Michael/intramolecular nucleophilic substitution pathway using potassium hydroxide in dichloromethane. Variously substituted vinyl selenones and 1H-indole-2-carboxamides or 1H-pyrrole-2-carboxamides have been employed with success in chemo and regio-selective processes. The introduction of an amino acid portion on the amidic function is well tolerated without racemization.



中文翻译:

使用乙烯基硒酮的吡嗪并吲哚和吡咯的多米诺法

在这里,我们公开了一种有效且灵活的方法来处理生物学上相关的3,4-二氢吡嗪并[1,2- a ]吲哚-1(2 H)酮和3,4-二氢吡咯并[1,2 - a ]吡嗪-1(2 H)通过在二氯甲烷中使用氢氧化钾的多米诺骨牌Michael /分子内亲核取代途径完成 在化学和区域选择性方法中已成功使用了各种取代的乙烯基硒酮和1 H-吲哚-2-甲酰胺或1 H-吡咯-2-甲酰胺。氨基酸部分在酰胺功能上的引入被很好地耐受而没有外消旋作用。

更新日期:2018-10-26
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