A facile synthesis of 2-substituted N-tert-butoxycarbonyl-N-methyl-1,3-propanediamines, key intermediates for the preparation of triplex DNA-specific intercalators
“…4-Acetyl-5,6-diphenylpyridazin-3(2H)-one (1) was prepared according to the reported method [9]. 6-Chloro-3-formylchromone (2) was prepared according to the reported method [10].…”
Section: Methodsmentioning
confidence: 99%
“…The mass spectrum of compound 18 exhibited a peak at m/z 314 (100%) corresponding to both molecular ion and base peak, which showed the higher stability of the mentioned compound. The presence of a methyl group at position 7 was deduced from its ability to condense with both benzaldehyde and 3-formyl-6-methylchromone [10] to afford 7-styrylpyrano[2,3-c]pyridazin-5-one 19 and 1-(chromon-3-yl)-2-(pyranopyridazin-7-yl)ethene 20 derivatives, respectively. In view of the wide biological activities of pyrazoles and pyrimidines, it was of interest to combine pyrazole and pyrimidine moieties with pyridazine in a molecular frame which this may enhance their biological applications.…”
“…4-Acetyl-5,6-diphenylpyridazin-3(2H)-one (1) was prepared according to the reported method [9]. 6-Chloro-3-formylchromone (2) was prepared according to the reported method [10].…”
Section: Methodsmentioning
confidence: 99%
“…The mass spectrum of compound 18 exhibited a peak at m/z 314 (100%) corresponding to both molecular ion and base peak, which showed the higher stability of the mentioned compound. The presence of a methyl group at position 7 was deduced from its ability to condense with both benzaldehyde and 3-formyl-6-methylchromone [10] to afford 7-styrylpyrano[2,3-c]pyridazin-5-one 19 and 1-(chromon-3-yl)-2-(pyranopyridazin-7-yl)ethene 20 derivatives, respectively. In view of the wide biological activities of pyrazoles and pyrimidines, it was of interest to combine pyrazole and pyrimidine moieties with pyridazine in a molecular frame which this may enhance their biological applications.…”
“…It is the adduct 10 that undergoes intramolecular 6π-electron cyclization, as evidenced by the isolation and characterization of intermediate 4,4-disubstituted-3,4-dihydroquinoline [30]. The two methodologies discussed above are quite general in scope, and a large array of other substituted quinolines [29,[32][33][34][35][36][37][38] and fused quinolines including acridines [39,40] can easily be prepared by the reaction of 2 or 7 with various basic/nucleophilic reagents [41][42][43][44][45].…”
This review summarizes the synthesis of quinolines and acridines by the reactions of anionically activated 2-(perfluoroalkyl)anilines. Mechanistic studies including isolation of the intermediate aza-ortho-xylylene are discussed.
“…Such a nucleophilic reagent is conveniently prepared by preliminary lithiation of a stannyl derivative, followed by suitable transmetalation to give the desired organometallic compound 55 (Scheme 3.29 ) [61] . …”
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