Products from furans. 1. Sunthesis and anticoccidial and antimicrobial activity of 5-amino-5,6-dihydro-6-methoxy-2-methyl-2-(4'-biphenylyl)-2H-pyran-3(4H)-ones and related compounds.

A Michael type addition of an amine to 6-methoxy-2-methyl-2-(4'-biphenylyl)-2H-pyran-3(6H)-one (1) dissolved in ether, benzene, or THF gave 5-amino derivatives of 5,6-dihydro-6-methoxy-2-methyl-2-(4'-biphenylyl)-2H-pyran-3(4H)-one (2). These by subsequent reduction with LiAlH4 were converted to 5-amino derivatives of 6-methoxy-2-methyl-2-(4'-biphenylyl)tetrahydro-2H-pyran-3-ol (3). Both isomers A and B of 1 (in regard to the methoxy group at C6) were used for the synthesis of 2 and 3. The in vitro antimicrobial activity of the amine adducts 2 was of the same order of magnitude as the starting material. Amine adducts in general, however, were by far more active as coccidiostats than the starting material and retained their activities when they were reduced. 5,6-Dihydro-6-methoxy-2-methyl-2-(4'-biphenylyl)-5-(dimethylamino)-2H-pyran-3(4H)-one hydrochloride (A) and 5,6-dihydro-6-methoxy-2-methyl-2-(4'-biphenylyl)-5-(dimethylamino)-2H-pyran-3(4H)-one hydrochloride (B), prepared from isomer A and B of 1, respectively, were the most active as coccidiostats. These compounds when administered orally to chickens 1 day prior to infection at a concentration 0.05% in their diet gave them total protection against Eimeria tenella.