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Heteroannulated Coumarins and Chromones from Chemical Transformations of 6,8‐Dimethylchromone‐3‐carbonitrile
Author(s) -
Ibrahim Magdy A.,
Badran AlShimaa,
Hashiem Salsabeel H.
Publication year - 2018
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.3354
Subject(s) - chemistry , malononitrile , ring (chemistry) , quinoline , nucleophile , derivative (finance) , chemical shift , organic chemistry , reagent , coumarin , medicinal chemistry , combinatorial chemistry , catalysis , financial economics , economics
A novel series of heterocyclic systems fused coumarins and chromones were efficiently synthesized from chemical transformations of 6,8‐dimethylchromone‐3‐carbonitrile ( 1 ) with a variety of carbon nucleophilic reagents. Ring opening ring closure reactions of carbonitrile 1 with cyanoacetohydrazide, malononitrile dimer (2‐aminoprop‐1‐ene‐1,1,3‐tricarbonitrile), and isomeric cyclohexanediones led to a diversity of coumarins and chromones fused nitrogen heterocyclic systems. Also, 1‐ethyl‐4‐hydroxyquinolin‐2(1 H )‐one ( 13 ) and 6‐ethyl‐4‐hydroxypyrano[3,2‐ c ]quinoline‐2,5(6 H )‐dione ( 14 ) are chemical equivalent towards carbonitrile 1 leading to benzo [ h ]chromeno[2,3‐ b ][1, 6] naphthyridine derivative 15 . Structures of the new synthesized products were deduced on the basis of their analytical and spectral data.