SYNTHESIS AND INVESTIGATION OF THE CHEMICAL AND PHYSICOCHEMICAL PROPERTIES OF 6-(1,4,5,6-TETRAHYDRO-6-OXO-3-PYRIDAZINYL)-2,3-DIHYDRO-2 INDOLINONES

Abstract

Acylation of 1-ethyl-3-(N,N-dimethyl)aminomethylene-1,2-dihydro-2-indolinone by succinic anhydride in the presence of aluminum chloride has been studied. PMR spectroscopy shows that this acylation leads to formation of a mixture of the 5- and 6-succinoyl derivatives with predominance of the latter (cis and trans isomers of both these products were found). The reaction of the latter with hydrazine hydrate gives hydrazinomethylene derivative of 2-indolinone, in reaction of which with various carbonyl compounds a series of oxindol hydrazones has been obtained. The reaction of these products with primary amines smoothly leads to transamination and the formation of enamines of 1,6-disubstituted 2-indolinone.

Authors: T. V. Golovko, N. P. Solov'eva, O. S. Anisimova, and V. G. Granik.

English Translation in Chemistry of Heterocyclic Compounds, 1999, 35 (10), pp 1167-1175

http://link.springer.com/article/10.1007/BF02323374