宝石-二氟喹啉-2(1H)-酮的三组分光化学环化/二硫代氨基甲酸盐形成。

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC Organic Letters Pub Date : 2024-10-29 DOI:10.1021/acs.orglett.4c03754

Fei Chen, Gangqing Shi, Yang Zheng, Qinghao Dong, Wei Peng, Rentian Wang, Erjun Hao, Xin Wang, Kai Sun

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摘要

本文描述了一种新型可见光诱导的 6-外-三位二氟甲基化环化反应和随后的羧基硫代酯化反应。该方法能在温和的条件下以中等到极好的产率高效地获得有价值的宝石-二氟喹啉-2(1H)-酮。广泛的氨基酸源兼容性，包括环吗啉、噻唑烷、硫代吗啉、吡咯烷、1,4-氧氮杂环庚烷、2,6-二甲基吗啉、哌嗪-1-羧酸叔丁酯和非环二乙胺、N-乙基丙-1-胺、N-苄基乙胺、N-苄基三甲基硅胺、二苄胺和 N-（4-甲氧基苄基）乙胺证明了这一策略的实用性。根据自由基抑制实验、可见光照射通断测试、表观量子效率（AQE）计算和荧光淬灭研究，提出了自由基-自由基交叉路线。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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Three-Component Photochemical Cyclization/Dithiocarbamate Formation of gem-Difluoro Quinolin-2(1H)-ones.

Herein, a novel visible-light-induced 6-exo-trig difluoromethylation cyclization and subsequent carbo-thioesterification reaction is described. This protocol allows efficient access to valuable gem-difluoro quinolin-2(1H)-ones in moderate to excellent yields under mild conditions. Broad amino sources compatibility, including cyclic morpholine, thiazolidine, thiomorpholine, pyrrolidine, 1,4-oxazepane, 2,6-dimethylmorpholine, tert-butyl piperazine-1-carboxylate and noncyclic diethylamine, N-ethylpropan-1-amine, N-benzylethanamine, N-benzyl-trimethylsilanamine, dibenzylamine, and N-(4-methoxybenzyl)ethanamine, demonstrated the practicability of this strategy. A radical-radical crossover route was proposed on the basis of radical inhibition experiments, visible light irradiation on-off test, apparent quantum efficiency (AQE) calculation, and fluorescence quenching studies.

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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.