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Visible-Light-Promoted Photoaddition of N-Nitrosopiperidines to Alkynes: Continuous Flow Chemistry Approach to Tetrahydroimidazo[1,2-a]pyridine 1-Oxides
Organic Letters ( IF 5.2 ) Pub Date : 2022-08-03 , DOI: 10.1021/acs.orglett.2c02402
Dilip V Patil 1 , Yulim Lee 1 , Hun Young Kim 2 , Kyungsoo Oh 1
Affiliation  

The photoaddition of N-nitrosopiperidines to terminal alkynes was effected under visible-light irradiation, in which a novel synthetic access to tetrahydroimidazo[1,2-a]pyridine 1-oxides was achieved via the dehydrogenative cycloisomerization of β-nitroso enamine intermediates. The decomposition pathways of N-nitrosamines, alkynes, and β-nitroso enamine intermediates were better handled in a continuous flow setting through the diffusion control of chemical species that negatively affected the formation of tetrahydroimidazo[1,2-a]pyridine 1-oxides under batch reaction conditions.

中文翻译:

N-亚硝基哌啶与炔烃的可见光促进光加成:四氢咪唑并[1,2-a]吡啶1-氧化物的连续流动化学方法

N-亚硝基哌啶与末端炔烃的光加成是在可见光照射下进行的,其中通过β-亚硝基烯胺中间体的脱氢环异构化获得了四氢咪唑并[1,2 - a ]吡啶1-氧化物的新合成途径。N-亚硝胺、炔烃和 β-亚硝基烯胺中间体的分解途径在连续流动环境中通过化学物质的扩散控制得到更好的处理,这些化学物质在间歇反应条件。
更新日期:2022-08-03
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