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Dibenzo[b,e][1,4]diazepin-1-ones and their Ring-Opened Derivatives: Revisited Synthesis, 2D NMR and Crystal Structure
Synlett ( IF 1.7 ) Pub Date : 2017-07-13 , DOI: 10.1055/s-0036-1590306
Norah Bennamane 1 , Oualid Talhi 2, 3 , Artur Silva 3 , Brahim Cherfaoui 1 , Houria Lakhdari 1, 2 , Rachid Ameraoui 2 , Filipe Almeida Paz 4 , Khaldoun Bachari 2 , Gilbert Kirsch 5 , Kolli Nejar-Bellara 1
Affiliation  

The synthesis of 2,3,4,5,10,11-hexahydro-1H-dibenzo[b,e][1,4]diazepin-1-ones was revisited and a catalyst-free method was established, by exploring the reactivity of 3-[(2-aminoaryl)amino]dimedones towards carbonylated electrophiles. 2D NMR and single-crystal X-ray diffraction studies were used to characterize the structures unequivocally and to review the mechanism leading to the formation of supposed positional isomers. The action of 3-[(2-aminoaryl)amino]dimedones on chromene-3-carboxylic acid, fumaryl, and oxalyl chloride has led to dibenzo[b,e][1,4]diazepin-1-one ring opening to produce novel Z-configured enaminone and linear diamides.

中文翻译:

二苯并[b,e][1,4]diazepin-1-ones 及其开环衍生物:重新合成、二维核磁共振和晶体结构

对2,3,4,5,10,11-六氢-1H-二苯并[b,e][1,4]diazepin-1-ones的合成进行了重新审视,并通过探索反应性,建立了一种无催化剂方法3-[(2-氨基芳基)氨基]二甲酮对羰基化亲电试剂的反应。2D NMR 和单晶 X 射线衍射研究用于明确表征结构并审查导致形成假定位置异构体的机制。3-[(2-氨基芳基)氨基]二甲酮对色烯-3-羧酸、富马酰和草酰氯的作用导致二苯并[b,e][1,4]二氮杂-1-one开环产生新型 Z 型烯胺酮和线性二酰胺。
更新日期:2017-07-13
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