Premium
Cyclization of N ‐benzyl cyanoacetamide: Novel synthesis and biological activity of pyrrole, pyrimidine, and pyran derivatives
Author(s) -
Hamed Eman O.,
Assy Mohamed G.,
Shalaby Adel M.,
Sayed Rawda E.
Publication year - 2020
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.3892
Subject(s) - chemistry , cyanoacetamide , thiourea , pyran , thio , benzaldehyde , ammonium thiocyanate , pyrrole , pyridine , carbon 13 nmr , pyrimidine , derivative (finance) , organic chemistry , medicinal chemistry , thiazole , stereochemistry , catalysis , financial economics , economics
Heteroannulation of N ‐Benzyl cyanoacetamide 1 to a new series of heterocycles has been developed. Thus, reaction of 1 with different polarized π systems afforded pyrrolo 4 , pyridone 6 , pyridine 8 , and diazapene 10 derivatives, respectively. N ‐Benzyl cyanoacetamide that undergo condensation reaction with salicylaldehyde yielded pyran derivative 11 . Nitrosation of 11 furnished condensed pyran 13 . Compound 11 reacted with benzaldehyde, carbon disulfide (cyclizing agent), and ammonium thiocyanate to provide pyrane 17 , thiazine 18 , and thiourea 20 derivatives, respectively. Cinnamoyl isothiocyanate was reacted with compound 11 to produce non‐isolable thiourea derivative 21 . The newly synthesized compounds have been characterized by infrared (IR), proton nuclear magnetic resonance ( 1 H NMR), and carbon nuclear magnetic resonance ( 13 C NMR) spectral data. The compounds were then evaluated for antibacterial and anticancer activities.