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

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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

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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（5和6_{) 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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