Homophtalonitrile for Multicomponent Reactions: Syntheses and Optical Properties of o-Cyanophenyl- or Indol-3-yl-Substituted Chromeno[2,3-c]isoquinolin-5-Amines |
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Authors: | Dr. Alexey A. Festa Olga A. Storozhenko Nikita E. Golantsov Dr. Karthikeyan Subramani Roman A. Novikov Snezhana O. Zaitseva Dr. Mikhail S. Baranov Prof. Alexey V. Varlamov Prof. Leonid G. Voskressensky |
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Affiliation: | 1. Organic Chemistry Department, Science Faculty, RUDN University, Miklukho-Maklaya st. 6, 117198 Moscow, Russian Federation;2. Engelhardt Institute of Molecular Biology, Russian Academy of Sciences, Vavilova st., 32, 119991 Moscow, Russian Federation;3. Institute of Bioorganic Chemistry, Russian Academy of Sciences, Miklukho-Maklaya 16/10, 117997 Moscow, Russian Federation;4. Institute of Bioorganic Chemistry, Russian Academy of Sciences, Miklukho-Maklaya 16/10, 117997 Moscow, Russian Federation Pirogov Russian National Research Medical University, Ostrovitianov 1, 117997 Moscow, Russian Federation |
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Abstract: | Malononitrile is a useful reagent for multicomponent reactions with hundreds of methods developed. In this paper, we suggest α-(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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Keywords: | chromeno[2,3-c]isoquinoline fluorescence multicomponent reactions organocatalysis sequential reactions |
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