Homophtalonitrile for Multicomponent Reactions: Syntheses and Optical Properties of o‐Cyanophenyl‐ or Indol‐3‐yl‐Substituted Chromeno[2, 3‐c]isoquinolin‐5‐Amines. Issue 1 (29th November 2018)

• Record Type: Journal Article
• Authors: 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.
• Is Part Of: ChemistryOpen. Volume 8:Issue 1(2019)
• Page Start: 23
• Page End: 30
• Publication Date: 2018-11-29
• Subjects: chromeno[2, 3-c]isoquinoline -- fluorescence -- multicomponent reactions -- organocatalysis -- sequential reactions; Chemistry -- Periodicals; 540; 540.5
• DOI: 10.1002/open.201800207
• Languages: English
• ISSNs: 2191-1363

Abstract

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‐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. Abstract : For the toolkit : Malononitrile is a useful reagent for multicomponent reactions with hundreds of methods developed. In this paper, α‐(cyano)‐ o ‐tolunitrile (homophtalonitrile) is suggested to work as a vinylogous malononitrile that can be employed in similar processes.