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Copper‐Catalyzed Multicomponent Synthesis of Fluorescent 2′‐Phenyl‐1′ H ‐spiro[fluorene‐9,4′‐naphtho[2,3‐ h ]quinoline]‐7′,12′‐dione Derivatives
Author(s) -
Meerakrishna Ramakrishnan Suseela,
Periyaraja Somasundharam,
Shanmugam Ponnusamy
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201600647
Subject(s) - chemistry , quinoline , fluorenone , fluorene , fluorescence , catalysis , pyrene , copper , conjugated system , aryl , derivative (finance) , coupling reaction , photochemistry , organic chemistry , combinatorial chemistry , polymer , physics , alkyl , quantum mechanics , financial economics , economics
Copper‐catalyzed multicomponent coupling reactions between ketones, alkynes, and amines (KA 2 coupling) by using 9‐fluorenones 1a – 1e , aryl alkynes 2a – 2g , and amino anthraquinones 3a and 3b afforded the highly conjugated, fluorescent spirofluorenonaphthoquinoline derivatives 4a – 4r in very good yields. The products obtained from 1‐aminoanthraquinone ( 3a ) and 1,4‐diaminoanthraquinone ( 3b ) appear different in color but both series of products show emission in the red region. An analogous reaction with 1‐aminopyrene ( 5 ) afforded the highly fluorescent hybrid pyrene‐fluorenone spirocycle derivative 6 , which shows emission in the deep blue region.