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An Environmentally Benign Multicomponent Cascade Reaction of 3-Formylchromones, 2-Naphthols, and Heterocyclic Ketal Aminals: Site-Selective Synthesis of Functionalized Morphan Derivatives
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2022-06-14 , DOI: 10.1021/acs.joc.2c00695
Ying-Gang Duan 1 , Yi-Hua Chen 1 , Zi-Han Lu 1 , Rong Huang 1 , Sheng-Jiao Yan 1
Affiliation  

A novel protocol has been developed for the preparation of highly functionalized 2-azabicyclo[3.3.1]nonane (morphan) derivatives by the interesting three-component cascade reaction of 3-formylchromones, 2-naphthol, and heterocyclic ketal aminals (HKAs) in the ionic liquid [BMIM]PF6 promoted by the organic base Et3N. A complex cascade reaction is required, which includes a 1,2-addition, two Michael reactions, two tautomerizations, and an N-alkylation accompanied by a ring-opening reaction and involving the cleavage of one C–O bond and the formation of four bonds (one C–N bond, one C–O bond, and two C–C bonds). As a result, functionalized morphans (5 and 6) bearing naphthalene-structured skeletons were prepared by simple heating of a mixture of 3-formylchromones, 2-naphthols, and HKAs in the environmentally friendly ionic liquid [BMIM]PF6. This protocol can be used in the synthesis of various morphans and is suitable for combinatorial and parallel syntheses of natural-like morphan derivatives. This approach has several advantages such as the use of an environmentally friendly solvent, simple and practical operation (multicomponent one-pot reaction), and satisfactory yields (65–88%).

中文翻译:

3-甲酰基色酮、2-萘酚和杂环缩酮缩醛胺的环境良性多组分级联反应:功能化吗啡衍生物的位点选择性合成

已经开发了一种新的方案,用于通过 3-甲酰基色酮、2-萘酚和杂环缩酮缩醛胺 (HKA) 的有趣的三组分级联反应制备高度官能化的 2-氮杂双环[3.3.1]壬烷 (吗啡) 衍生物。离子液体 [BMIM]PF 6由有机碱 Et 3 N 促进。需要一个复杂的级联反应,包括 1,2-加成、两个迈克尔反应、两个互变异构化和伴随环的 N-烷基化反应开放反应,涉及一个 C-O 键的断裂和四个键的形成(一个 C-N 键、一个 C-O 键和两个 C-C 键)。因此,功能化吗啡(56) 通过在环保离子液体 [BMIM]PF 6中简单加热 3-甲酰基色酮、2-萘酚和 HKAs 的混合物,制备了带有萘结构的骨架。该协议可用于各种吗啡的合成,适用于类天然吗啡衍生物的组合合成和平行合成。这种方法有几个优点,例如使用环保溶剂、操作简单实用(多组分一锅反应)和令人满意的收率(65-88%)。
更新日期:2022-06-14
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