SYNTHESIS OF PYRIDINE DERIVATIVES BY THE THREE-COMPONENT CONDENSATION OF A β-DICARBONYL COMPOUND, β-ENAMINOCARBONYL COMPOUND, AND ETHYL ORTHOFORMATE

Abstract

The major products of the three-component condensation of a β-dicarbonyl compound, β-enaminocarbonyl compound, and ethyl orthoformate are pyridine derivatives. The reaction of 1,3-cyclohexanedione or dimedone, the enamino ketones obtained from these diones, and ethyl orthoformate gives octahydroacridinediones, while the reaction of dimedone, ethyl β-aminocrotonate, and ethyl orthoformate gives a tetrahydroquinoline derivative. The structures of the minor products were established in some cases. The reduction of 3,3,6,6-tetramethyl-1,2,3,4,5,6,7,8-octahydro-1,8-acridinedione by LiAlH4 proceeds with retention of the pyridine ring and leads to the corresponding octahydroacridinediol.

Author: A. N. Pyrko.

English Translation in Chemistry of Heterocyclic Compounds, 1999, 35 (6), pp 688-694

http://link.springer.com/article/10.1007/BF02251627