PREPARATION OF ANTIBIOTICS CONTAINING LACTAM RING

摘要

PURPOSE:A seleninic amide derivative is formed in the 7-or 6-positon of wide ranges of cephalosporins and penicillins by using a seleniny halide, thereby permitting ready introduction of substituent in the position in high yield. CONSTITUTION:7-Aminocephem or 6-aminopenam derivative of formula II [R<3> is protected or unprotected carboxyl group; Z is group of formula IX or X (R<4> is unreactive group)] is reacted with a seleninyl halide of formula III (R<1> is substituted aromatic group; X is halogen) in the presence of a base to form seleninic amide derivative formula IV (R<2> is lower alkyl). The resultant seleninic amide is oxidized with an oxidizing agent to form a seleninic imino derivative of formula V, which is reacted with a compound of formula VI (R<2> is lower alkyl). The product of fomulaVII is reacted with a compound of fomula VIII (R<5> is residue of carboxylic acid) to prepare 7-alkoxyacylaminocephem or penam derivative of formula I.