当前位置: X-MOL 学术Synth. Commun. › 论文详情
Our official English website, www.x-mol.net, welcomes your feedback! (Note: you will need to create a separate account there.)
Hantzsch one-pot multicomponent synthesis of a novel series of bis(9,10-diarylhexahydroacridine-1,8-diones)
Synthetic Communications ( IF 1.8 ) Pub Date : 2021-07-29 , DOI: 10.1080/00397911.2021.1956541
Amr M. Abdelmoniem 1 , Hadeel F. Hammad 1 , Ahmed F. Darweesh 1 , Mahfouz A. Abdelaziz 1 , Ismail A. Abdelhamid 1 , Ahmed H. M. Elwahy 1
Affiliation  

Abstract

Efficient procedures have been developed for the synthesis of novel series of bis(9,10-diaryl-hexahydroacridine-1,8-diones) in which the two acridine moieties were linked to aliphatic, aromatic, or heteroaromatic spacers via ether or ester linkages. The target products were obtained in good to excellent yields via a multi-component reaction of the appropriate aromatic amine, 5,5-dimethyl-1,3-cyclohexanedione, and the corresponding bis-aldehydes. The reactions were also proceeded to give the target products in good yields via a multi-component reaction of the appropriate cyclic enamines, and the corresponding bis-aldehydes under similar conditions. Bis-alkylation of the appropriate hexahydroacridine-1,8-dione with the corresponding dihalo compound in a basic medium was also proved to be an effective strategy for the synthesis of the target products. The multi-component reaction of the aromatic amine, bis-aldehydes, and barbituric acid or 1,3-dimethylbarbituric acid, instead of 5,5-dimethyl-1,3-cyclohexanedione, afforded the corresponding Knoevenagel condensation adducts in good yield and unfortunately, the expected bis-tetrahydropyrimido[4,5-b]quinolines could not be isolated.



中文翻译:

Hantzsch 一锅多组分合成一系列新型双(9,10-二芳基六氢吖啶-1,8-二酮)

摘要

已经开发了用于合成新型(9,10-二芳基-六氢吖啶-1,8-二酮)系列的有效程序,其中两个吖啶部分通过醚或酯键连接到脂肪族、芳香族或杂芳香族间隔基。通过适当的芳香胺、5,5-二甲基-1,3-环己二酮和相应的醛的多组分反应,以良好至极好的收率获得目标产物。将反应物也进行,得到高产率的目标产物通过合适的环状烯胺的多组分反应,和相应的-醛类似的条件下。适当的六氢吖啶-1,8-二酮与相应的二卤化合物在碱性介质中的烷基化也被证明是合成目标产物的有效策略。芳香胺、醛和巴比妥酸或 1,3-二甲基巴比妥酸而不是 5,5-二甲基-1,3-环己二酮的多组分反应以良好的收率提供了相应的 Knoevenagel 缩合加合物,但不幸的是,预期的-四氢嘧啶并[4,5- b ]喹啉无法分离。

更新日期:2021-08-23
down
wechat
bug