- Synthesis of variously 9,9-dialkylated octahydropyrimido [3,4-a]-s-triazines with potential antifungal activity
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9,9-Dialkyloctahydropyrimido[3,4-a]-s-triazines were synthesized by iminodimethylation reaction between a 5,5-dialkyl-6-aminopyrimidine-2,4(3H,5H)-dione, a substituted aniline and two moles of formaldehyde. The synthesis of 5,5-dialkyl-6-aminopyrimidinedione consisted of the condensation of urea with ethyl 2,2-dialkylcyanoacetates. 18 Octahydropyrimido[3,4-a]-s-triazines were synthesized and compounds resulting from a supplementary aminomethylation were also obtained. Most of these compounds were tested for antifungal activity in vitro. Only 9,9-dibutyl-6,8-dioxo-3(2-chlorophenyl)2,3,4,5,6,7,8,9-octahydropyrimido[3, 4-a]-s-triazine showed some activity against Microsporum canis.
- Ghaib, Amar,Menager, Sabine,Verite, Philippe,Lafont, Olivier
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p. 109 - 116
(2007/10/03)
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- Process for producing cyanovaleric esters and caprolactam
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Caprolactam can be produced with an economical advantage without formation of by-products in a high yield by subjecting adipic acid and adiponitrile to interchange reaction at an elevated temperature, adding an alcohol directly to the interchange reaction mixture without isolating the resulting cyanovaleric acid to esterify the cyanovaleric acid with said alcohol into a cyanovaleric ester, reducing the cyanovaleric ester with a catalyst into an aminocaproic ester, heating the aminocaproic ester in a polyhydric alcohol having a higher boiling point than that of caprolactam to convert the ester into caprolactam, isolating the caprolactam by distillation and recycling the liquid distillation residue to the system for heating said polyhydric alcohol and said aminocaproic ester.
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- Stereospecific and Stereoselective Reactions. V. Alkylation of Active Methylene Compounds by the Use of Alcohols, Diethyl Azodicarboxylate, and Triphenylphosphine
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The reagent formed by the reaction of diethyl azodicarboxylate (1) and triphenylphosphine (2) reacted with alcohols and ethyl cyanoacetate (6) to give alkylated products in 30 - 80percent yields.When ethyl acetoacetate, 1,3-1,3-coclopentanedione, or 1,3-cyclohexanedione was used in place of 6, the corresponding O-alkylated products were obtained.The reaction of either (S)-(-)-ethyl lactate or (S)-(-)-ethyl 2-hydroxy-3-phenylpropionate with 1, 2, and 6, followed by hydrolysis resulted in the formation of (S)-(-)-methylsuccinic acid or (S)-(-)-benzylsuccinic acid.The results indicate that nearly complete inversion of the configuration takes place in the alkylation step.
- Kurihara, Toshio,Sugizaki, Masaru,Kime, Itaru,Wada, Makoto,Mitsunobu, Oyo
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p. 2107 - 2112
(2007/10/02)
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