Photosensitized Intramolecular [2+2] Cycloaddition of 1H-Pyrrolo[2,3-b]pyridines Enabled by the Assistance of Lewis Acids

被引:12
作者
Arai, Noriyoshi [1 ]
Ohkuma, Takeshi [1 ,2 ]
机构
[1] Hokkaido Univ, Fac Engn, Div Appl Chem, Sapporo, Hokkaido 0608628, Japan
[2] Hokkaido Univ, Fac Engn, Frontier Chem Ctr, Sapporo, Hokkaido 0608628, Japan
关键词
N-BENZOYLINDOLE; HETEROCYCLES; PHOTOCHEMISTRY; CYCLIZATION; ACTIVATION; SCAFFOLDS; ALKENES; ACCESS; POTENT;
D O I
10.1021/acs.joc.0c02231
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The [2+2] photocycloaddition of alkenyl-tethered 1H-pyrrolo[2,3-b]pyridine derivatives sensitized with 3',4'-dimethoxyacetophenone under irradiation by a high-pressure mercury lamp through Pyrex glass was dramatically accelerated by the addition of Lewis acids, preferably Mg(OTf)(2), to give the products stereoselectively in high yields. The reaction without a Lewis acid gave only small amounts of the [2+2] cycloaddition products. Conformational fixation of the substrates by coordination with a Lewis acid was presumed to facilitate the cycloaddition.
引用
收藏
页码:15717 / 15725
页数:9
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