Cyclocondensations of acetylacetone with cyanoacetamide or N-alkylcyanoacetamides in the presence of NaA zeolite afford 4,6-dimethyl-2-oxonicotinonitrile or 1-alkyl-4,6-dimethyl-2-oxonicotinonitriles respectively. The condensation of 3-hydroxyiminopenta-2,4-dione with cyanoacetamide in the presence of NaA zeolite furnished 4,6-dimethyl-5-nitroso-2-oxonicotinonitrile.2-Oxonicotinonitriles exhibit vasodilating effect [1] and immunosuppressive activity [2]. They are constituents of plant growth regulators, herbicides, and defoliants for they are modulators of chlorophyll biosynthesis in plants [3].2-Oxonicotinonitriles IIV are commonly prepared by the cyclocondensation of cyanoacetamide or its N-alkyl derivatives with acetylacetone [4] or 3-hydroxyiminopenta-2,4-dione [5]. The reaction is carried out either in a buffer solution at pH 9.1 [6] or in the presence of catalysts. As catalysts were applied potassium carbonate [6], secondary and tertiary amines [47], and lipase from Candida cylindracea [8].We suggested to use as catalyst in this reaction the NaA zeolite for zeolites were known to catalyse the aldol condensation of acetone [9]. It actually proved that acetylacetone entered into cyclocondensation with the cyanoacetamide (V) and N-alkylcyanoacetamides VI and VII in the presence of NaA zeolite. The reaction gave rise to 1-alkyl-4,6-dimethyl-2-oxonicotinonitriles IIII. 0H&2&+ &20H &1&+ &21+5 1D$ 1 0H &1 2 5 0H , ,,, B 9 9,, B
Pyridine derivatives R 0380Zeolites in the Synthesis of 1-Alkyl-2-oxonicotinonitriles. -Cyclocondensation of 1,3-diones with cyanoacetamides in the presence of zeolite NaA affords the title 2-oxonicotinonitriles in good to excellent yields. -(SEMICHENKO, E. S.; VASILENKO, F. N.; TOVBIS, M. S.; BELYAE, E. Y.; Russ. J. Org. Chem. 41 (2005) 2, 313-314; Sib. State Technol. Univ., Krasnoyarsk 660049, Russia; Eng.) -A. Forchert 40-152
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