Claims
- 1. A process for the preparation of a compound of formula III ##STR13## wherein R.sub.1 is hydrogen, C.sub.1 -C.sub.12 alkyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.1 -C.sub.4 alkoxy-C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.2 haloalkyl, phenyl, benzyl, phenethyl, phenpropyl, phenbutyl or phenpentyl, or a phenyl, benzyl, phenethyl, phenpropyl, phenbutyl or phenpentyl radical that is mono- or di-substituted by halogen, C.sub.1 -C.sub.5 alkyl, C.sub.1 -C.sub.2 haloalkyl, methoxy and/or ethoxy; R.sub.2 is hydrogen, C.sub.1 -C.sub.6 alkyl or C.sub.3 -C.sub.6 cycloalkyl, or is phenyl that is unsubstituted or substituted by C.sub.1 -C.sub.12 alkyl, halogen or by C.sub.1 -C.sub.12 haloalkyl; or R.sub.1 and R.sub.2 together form a saturated or unsaturated 3- to 7-membered carbocycle; R.sub.3 is hydrogen or C.sub.1 -C.sub.6 alkyl and Z is --N.dbd.CH-- or --NH--CH.sub.2 --,
- which process comprises reacting an aminotriazinone of formula I ##STR14## wherein R.sub.1, R.sub.2 and R.sub.3 have the meanings above with an aldehyde of formula IV ##STR15## and, if desired, convening the resulting pyridyl-methyleneamino-triazinone by selective reduction into pyridyl-methylamino-triazinone,
- wherein the aminotriazinone of the formula I is prepared by the solvolysis of a compound of formula II ##STR16## wherein R.sub.1 is hydrogen, C.sub.1 -C.sub.12 alkyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.1 -C.sub.4 alkoxy-C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.2 haloalkyl, phenyl, benzyl, phenethyl, phenpropyl, phenbutyl or phenpentyl, or a phenyl, benzyl, phenethyl, phenpropyl, phenbutyl or phenpentyl radical that is mono- or di-substituted by halogen, C.sub.1 -C.sub.5 alkyl, C.sub.1 -C.sub.2 haloalkyl, methoxy and/or ethoxy; R.sub.2 is hydrogen, C.sub.1 -C.sub.6 alkyl or C.sub.3 -C.sub.6 cycloalkyl, or is phenyl that is unsubstituted or substituted by C.sub.1 -C.sub.12 alkyl, halogen or by C.sub.1 -C.sub.12 haloalkyl; or R.sub.1 and R.sub.2 together form a saturated or unsaturated 3- to 7-membered carbocycle; R.sub.3 is hydrogen or C.sub.1 -C.sub.6 alkyl; and R.sub.4 is H, C.sub.1 -C.sub.4 -alkyl, C.sub.3 -C.sub.6 -cycloalkyl, C.sub.1 -C.sub.4 -alkyl substituted by 1 to 9 chlorine atoms, C.sub.1 -C.sub.3 -alkoxy, C.sub.1 -C.sub.3 -alkylthio, phenyl, pyridyl, or phenyl or pyridyl which is substituted with 1 to 3 substituents selected from the group of halogen, methyl, ethyl, methoxy, methylthio or nitro, in the presence of gaseous hydrogen chloride in an alcoholic medium.
- 2. A process according to claim 1 wherein R.sub.1 is hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.5 cycloalkyl, phenyl or phenyl that is mono- or di-substituted by halogen, C.sub.1 -C.sub.3 alkyl, methoxy or ethoxy, each of R.sub.2 and R.sub.3 is hydrogen or C.sub.1 -C.sub.4 alkyl and Z is --N.dbd.CH-- or --NH--CH.sub.2 --.
- 3. A process according to claim 2 wherein R.sub.1 is hydrogen, C.sub.1 -C.sub.4 alkyl, cyclopropyl or phenyl; R.sub.2 is hydrogen, methyl or ethyl; and R.sub.3 is hydrogen or methyl; and Z is --N.dbd.CH-- or --NH--CH.sub.2 --.
- 4. A process according to claim 3 wherein the compound of formula III is 6-methyl-4-(pyridin-3-ylmethyleneamino)-4,5-dihydro- 1,2,4-triazin-3(2H)-one.
Parent Case Info
This is a continuation-in-part of application Ser. No. 08/040,691, filed Mar. 31, 1993, now abandoned.
US Referenced Citations (2)
Number |
Name |
Date |
Kind |
4931439 |
Kristinsson |
Jun 1990 |
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4996325 |
Kristinsson |
Feb 1991 |
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Foreign Referenced Citations (1)
Number |
Date |
Country |
0433218 |
Jun 1991 |
EPX |
Continuation in Parts (1)
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Number |
Date |
Country |
Parent |
40691 |
Mar 1993 |
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