期刊
CHEMISTRYOPEN
卷 8, 期 1, 页码 23-30出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/open.201800207
关键词
chromeno[2,3-c]isoquinoline; fluorescence; multicomponent reactions; organocatalysis; sequential reactions
资金
- RUDN University Program 5-100
Malononitrile is a useful reagent for multicomponent reactions with hundreds of methods developed. In this paper, we suggest alpha-(cyano)-o-tolunitrile (homophtalonitrile) to work as a vinylogous malononitrile. Thus, a organocatalytic pseudo-three-component reaction of homopthalonitrile (2 equiv) and o-hydroxybenzaldehyde, leading to the diastereoselective formation of 5-amino-12H-chromeno[2,3-c]isoquinolin-12-yl)(cyano)methyl)benzonitriles, was discovered. The possibility to employ other nucleophiles was demonstrated for indoles, and a sequential three-component reaction of homophtalonitrile, o-hydroxybenzaldehyde, and (aza)indole, giving 12-(1H-Indol-3-yl)-12H-chromeno[2,3-c]isoquinolin-5-amines, was developed. The photophysical properties of the synthesized compounds have been studied, revealing high fluorescence quantum yields (42-70 %) for indol-3-yl substituted 12H-chromeno[2,3-c]isoquinolin-5-amines and reversible fluorescence quenching under acidic conditions.
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