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在深共熔溶剂介质中一锅法顺序合成烯基化二氢喹啉酮和六氢吖啶酮

One-Pot Sequential Synthesis of Alkenylated Dihydroquinolinones and Hexahydroacridinones in Deep Eutectic Solvent Medium.

作者信息

Suresh Sundararajan, Nawaz Khan Fazlur Rahman

机构信息

Organic and Medicinal Chemistry Research Laboratory, School of Advanced Sciences, Vellore Institute of Technology, Vellore 632014, Tamil Nadu, India.

出版信息

ACS Omega. 2024 Aug 16;9(34):36198-36219. doi: 10.1021/acsomega.4c02058. eCollection 2024 Aug 27.

DOI:10.1021/acsomega.4c02058
PMID:39220520
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11360033/
Abstract

The sequential synthesis of -heterocycles from saturated ketones poses significant challenges and has rarely been reported. Herein, an efficient synthesis of alkenylated dihydroquinolinones and hexahydroacridinones is achieved from saturated ketones or via dehydrogenation, cyclization, oxidation, and α-alkenylation in choline chloride-based deep eutectic solvent (DES) medium. This strategy provides alkenylated dihydroquinolinones and hexahydroacridinones in excellent yield from low-cost, readily available starting materials under environmentally benign conditions. Furthermore, the synthesized compounds (, , , and ) were investigated for their photophysical properties through absorption and emission spectral studies.

摘要

从饱和酮顺序合成杂环面临重大挑战，且鲜有报道。在此，通过在氯化胆碱基低共熔溶剂（DES）介质中进行脱氢、环化、氧化和α-烯基化反应，从饱和酮或实现了烯基化二氢喹啉酮和六氢吖啶酮的高效合成。该策略在环境友好条件下，以低成本、易于获得的起始原料，高产率地提供了烯基化二氢喹啉酮和六氢吖啶酮。此外，通过吸收和发射光谱研究对合成的化合物（、、和）的光物理性质进行了研究。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d50c/11360033/765427e7010d/ao4c02058_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d50c/11360033/f1d99d74c5fc/ao4c02058_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d50c/11360033/71b93473cf3b/ao4c02058_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d50c/11360033/69ca1cc225ad/ao4c02058_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d50c/11360033/bb759a937955/ao4c02058_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d50c/11360033/20bd80d30d19/ao4c02058_0008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d50c/11360033/ad0e1c97a88b/ao4c02058_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d50c/11360033/b251dc651496/ao4c02058_0009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d50c/11360033/d028e8273f66/ao4c02058_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d50c/11360033/765427e7010d/ao4c02058_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d50c/11360033/f1d99d74c5fc/ao4c02058_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d50c/11360033/71b93473cf3b/ao4c02058_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d50c/11360033/69ca1cc225ad/ao4c02058_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d50c/11360033/bb759a937955/ao4c02058_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d50c/11360033/20bd80d30d19/ao4c02058_0008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d50c/11360033/ad0e1c97a88b/ao4c02058_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d50c/11360033/b251dc651496/ao4c02058_0009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d50c/11360033/d028e8273f66/ao4c02058_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d50c/11360033/765427e7010d/ao4c02058_0004.jpg

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