ChemInform Abstract: Cyclization Reactions of Nitriles. Part 56. Synthesis and Transformations of Substituted 6‐Aryl‐4‐(2‐thienyl)‐3‐cyanopyridine‐2( 1H)‐thiones.

Abstract

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Synthesis and Biological Evaluation of New Pyridothienopyrimidine Derivatives as Antibacterial Agents and Escherichia coli Topoisomerase II Inhibitors

“…The synthesis of the target pyridothienopyrimidines ( 2a , b – 8a , b ) was achieved via various reactions, as depicted in Scheme 1 ; Scheme 2 . The starting 3-amino-6-phenylthieno[2,3- b ]pyridine-2-carboxamides 1a , b were prepared [ 44 , 45 ] and underwent a cyclocondensation reaction with cyclohexanone in refluxing N,N -dimethyformamide containing anhydrous zinc chloride to produce 1’ H -spiro[cyclohexane-1,2’-pyrido[3’,2’:4,5]thieno[3,2- d ]pyrimidin]-4’(3’ H )-ones 2a , b . The chemical structures of 2a , b were confirmed by their 1 H NMR spectra, which revealed signals at 1.21–2.02 ppm, corresponding to the 5CH 2 protons of the spiro cyclohexane ring and two signals corresponding to the 2NH groups of the pyrimidinone ring at 4.53 and 7.90 ppm and 4.90 and 7.88 ppm for 2a and 2b , respectively.…”

“…The nomenclature of the new synthesized compounds is according to the IUPAC system. The starting 3-amino-6-phenylthieno[2,3- b ]pyridine-2-carboxamides 1a , b were prepared as per reported methods [ 44 , 45 ].…”