Novel fluorine-containing 1,7-phenanthrolines with a variety of substituents at the 3-position were easily synthesized in moderate to high yields by the pyridine-ring formation reaction of N-propargyl-6,8-bis(trifluoroacetyl)quinolin-5-amine with various amines, thiols, alcohols, and phenols.
6,8-Bis(trifluoroacetyl)quinolin-5-amine reacted easily with various aldehydes in the presence of aqueous ammonia to afford trifluoromethylated pyrido[2,3-h]quinazoline derivatives and 1,7-phenanthroline derivatives in good to excellent yields. Under almost the same conditions, the use of ketones instead of aldehydes gave 1,7-phenanthroline derivatives selectively, except in the case of cyclohexanone.
Facile and Convenient Syntheses of Fluorine-Containing Pyrido[2,3-h]quinazolines and 1,7-Phenanthrolines by Condensation Reactions of 6,8-Bis(trifluoroacetyl)quinolin-5-amine with CarbonylCompounds. -A two-step sequence involving the condensation of quinolin-5-amine (I) with aldehydes and ammonia followed by dehydrogenation with DDQ allows the synthesis of pyridoquinazolines (V), (VIII), and (X). 1,7-Phenanthrolines (IV) are obtained as by-product when aldehydes (II) are used. The condensation with ketones (XI) proceeds under similar conditions to give analogues (XII). -(HINOSHITA, M.; SHIBATA, D.; HATAKENAKA, M.; OKADA*, E.; Synthesis 2011, 17, 2754-2760, http://dx.
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