Open AccessHomophtalonitrile for Multicomponent Reactions: Syntheses and Optical Properties of o ‐Cyanophenyl‐ or Indol‐3‐yl‐Substituted Chromeno[2,3‐ c ]isoquinolin‐5‐Amines
Author(s) -
Festa Alexey A.,
Storozhenko Olga A.,
Golantsov Nikita E.,
Subramani Karthikeyan,
Novikov Roman A.,
Zaitseva Snezhana O.,
Baranov Mikhail S.,
Varlamov Alexey V.,
Voskressensky Leonid G.
Publication year - 2019
Publication title -
chemistryopen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.644
H-Index - 29
ISSN - 2191-1363
DOI - 10.1002/open.201800207
Subject(s) - malononitrile , chemistry , reagent , indole test , nucleophile , quenching (fluorescence) , fluorescence , component (thermodynamics) , reaction conditions , medicinal chemistry , combinatorial chemistry , organic chemistry , photochemistry , catalysis , physics , quantum mechanics , thermodynamics
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‐12 H ‐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‐(1 H ‐Indol‐3‐yl)‐12 H ‐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 12 H ‐chromeno[2,3‐ c ]isoquinolin‐5‐amines and reversible fluorescence quenching under acidic conditions.