1-amino-1,2,3,4-tetrahydropyridine-2,3-dicarboxylic acid...

C - Chemistry – Metallurgy – 07 – D

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C07D 211/90 (2006.01) C07D 213/803 (2006.01) C07D 213/81 (2006.01) C07D 471/04 (2006.01) C07D 491/048 (2006.01)

Patent

CA 1260469

Novel 1-amino-1,2,3,4-tetrahydropyridine-2,3- dicarboxylic acid derivatives and 1,4-dihydropyridine-2,3- dicarboxylic acid derivatives. ABSTRACT A process for producing pyridine-2,3-dicarboxylic acid derivatives of the formula I Image (I) is described. The process is based on the cleavage of HNR10R11 from 1-amino-1,2,3,4-tetrahydropyridine-2,3-dicarboxylic acid derivatives of the formula II Image (II) to give 1,4-dihydropyridine-2,3-dicarboxylic acid derivatives of the formula III Image (III) and subsequent oxidation of these compounds to obtain pyridine-2,3-dicarboxylic acid derivatives of the formula I. According to one variant of the process, the 1,4-dihydropyridine- 2,3-dicarboxylic acid derivatives of the formula III are obtained directly, without isolation of the intermediately formed 1-amino-1,2,3,4-tetrahydropyridine-2,3-dicarboxylic acid derivatives of the formula II, by reaction of .alpha.,.beta.-unsatu- rated hydrazones of the formula IV Image (IV) with ethene-1,2-dicarboxylic acid derivatives of the formula V Image (V); and subsequently oxidised to pyridine-2,3-dicarboxylic acid derivatives of the formula I. In the above formulae, R1, R2, R3, R4, R5, R10 and R11 have the meanings defined in claim 1. This divisional relates to the novel intermediates of formula II and III useful in this process. The pyridine-2,3-dicarboxylic acid derivatives of the formula I are intermediates for producing herbicidal active substances.

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