Process for producing pyridine-2,3-dicarboxylic acid derivatives

Details Process for producing pyridine-2,3-dicarboxylic acid derivatives Process for producing pyridine-2,3-dicarboxylic acid derivatives

1985-08-02

1988-06-28

Jiles, Henry R.

Organic compounds -- part of the class 532-570 series

Organic compounds

Four or more ring nitrogens in the bicyclo ring system

544128, 544131, 546 84, 546 92, 546112, 546113, 546115, 546116, 546156, 546183, 546187, 546193, 546194, 546281, 546291, 546296, 546299, 546316, 546318, 546321, 546322, C07D213803, C07D21193, C07D47104, C07D491048

Patent

active

047540338

ABSTRACT:
A process for producing pyridine-2,3-dicarboxylic acid derivatives of the formula ##STR1## is described. The process is based on the cleavage of HNR.sub.10 R.sub.11 from 1-amino-1,2,3,4-tetrahydropyridine-2,3-dicarboxylic acid derivatives of the formula II ##STR2## to give 1,4-dihydropyridine-2,3-dicarboxylic acid derivatives of the formula III ##STR3## 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.-unsaturated hydrazones of the formula IV ##STR4## with ethene-1,2-dicarboxylic acid derivatives of the formula V ##STR5## and subsequently oxidized to pyridine-2,3-dicarboxylic acid derivatives of the formula I. In the above formulae, R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.10 and R.sub.11 have the meanings defined in claim 1.
The pyridine-2,3-dicarboxylic acid derivatives of the formula I are intermediates for producing herbicidal active substances.

REFERENCES:
Serckx-Poncin, B. et al, Tetrahedron Letters, vol. 23, No. 32, pp. 3261-3264 (1982).

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