Substituted 3-and 5-formylpyridin-2-ones in the synthesis of 1-aryl-1,6-naphthyridinone derivatives

作者：Medvedeva M I; Tugusheva N Z; Alekseeva L M; Evstratova M I; Kiselev S S; Chernyshev V V; Avramenko G V; Granik V G^*

来源：Russian Chemical Bulletin, 2009, 58(11): 2336-2346.

DOI：10.1007/s11172-009-0325-7

• enamino amides
• dimethylformamide acetals
• 4-arylamino-2-oxo-1,2-dihydropyridine-3-carbonitriles
• 3-arylamino-2-cyano-5-dimethylamino-N-[(dimethylamino)methylidene]penta- 2,4-dien amides
• 4-arylamino-5-formyl-2-oxo-1,2-dihydropyridine-3-carbonitriles
• 4-arylamino-2-oxo-1,2-dihydropyridine-3-carbaldehydes
• 1-aryl-3,8-dicyano-2-imino-1,6-naphthyridine-2,5(1H
• 6H)-diones
• 1-aryl-5-chloro-3-nitro-1,6-naphthyridine-2(1H)-ones
• the Knoevenagel reaction
• X
• ray diffraction
• HPLC

New 1-aryl-6-[2-(dimethylamino)vinyl]-4-oxo-1,4-dihydropyrimidine-5-carbonitriles and 4-arylamino-2-oxo-1,2-dihydropyridine-3-carbonitriles containing electron-withdrawing substituents in the benzene ring were synthesized from enamino amides and dimethylformamide dialkylacetals. The influence of various dimethylformamide acetals on the yield of 3-(4-chloroanilino)-2-cyano-5-(dimethylamino)penta-2,4-dienoic acid N-(dimethylamino)methylideneamide was investigated in the reaction of these acetals with 3-(4-chloroanilino)-2-cyanocrotonamide. New 4-arylamino-5-formyl-2-oxo-1,2-dihydropyridine-3-carbonitriles and 4-arylamino-2-oxo-1,2-dihydropyridine-3-carbaldehydes containing electron-withdrawing substituents in the benzene ring were synthesized. The latter compounds were converted into new substituted 1,6-naphthyridinones by the action of various CH acids. A new approach to the synthesis of 4-(4-fluoroanilino)-5-formyl-2-oxo-1,2-dihydropyridine-3-carbonitrile using dimethylformamide diisopropylacetal under mild conditions was developed. The comparative reactivity of the formyl group in the reactions of 4- arylamino-5-formyl-2-oxo-1,2- dihydropyridine-3-carbonitriles and in 4-arylamino-2-oxo-1,2- dihydropyridine-3-carbaldehydes with malononitrile was determined using HPLC.

• 出版日期2009-11
• 单位北京化工大学