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Synthesis of Various Fused Heterocyclic Rings from Oxoindenyl Esters and their Pharmacological and Antimicrobial Evaluations
Author(s) -
Mahmoud Naglaa F. H.,
Elsayed Galal A.,
Ismail Mahmoud F.
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.3065
Subject(s) - chemistry , isoquinoline , antimicrobial , hydrazine (antidepressant) , reagent , nucleophilic substitution , nucleophile , acrylate , organic chemistry , proton nmr , combinatorial chemistry , mass spectrum , monomer , ion , polymer , chromatography , catalysis
Methyl ( Z )‐2‐ O ‐carboxyphenyl‐3‐(3,4,5‐trimethoxyphenyl)acrylate 1 was prepared and cyclized in different conditions to give the indenone 2 . Also, 1 was utilized to synthesize the isochroman dione derivatives 8 , 10 , 12 , and 13 and isoquinoline derivatives 16 and 18 . On the other hand, the reactions of 2 with some nucleophilic reagents such as Grignard reagents and hydrazine derivatives afforded the novel heterocyclic systems 3 , 4a , b , 5 , 6 , and 7 . Isochroman dione 12 was allowed to react with primary amines to give 14 , 15 , 17 , and 19 . The structures of the synthesized new compounds have been elucidated by spectroscopic data: IR, 1 H‐NMR, 13 C‐NMR, mass spectra, and elemental analyses. The antimicrobial and anticancer activities have been evaluated.