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Synthesis of carbon‐ 14 labelled antimicrobial agents, I, synthesis of 1,4‐dihydro‐1‐methoxy‐6,7‐methylenedioxy‐4‐oxo‐quinoline‐3‐carboxylic‐3‐ 14 C acid (AB‐206‐3‐ 14 C)
Author(s) -
Yoshitake A.,
Makari Y.,
Endo M.
Publication year - 1974
Publication title -
journal of labelled compounds
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0022-2135
DOI - 10.1002/jlcr.2590100408
Subject(s) - chemistry , methylenedioxy , medicinal chemistry , methylene , anhydrous , yield (engineering) , organic chemistry , carboxylic acid , antimicrobial , alkyl , materials science , halogen , metallurgy
1,4‐Dihydro‐1‐methoxy‐6,7‐methylenedioxy‐4‐oxoquinoline‐3‐carboxylic acid (I) (AB‐206), a new synthetic antimicrobial agent, was labelled with carbon‐14 at C‐3 position of the quinolinone ring for metabolic studies. The synthesis was achieved according to the reaction schemes shown in Fig. 1 and 4; which involved a newly devised key‐reaction, the condensation of diethyl malonate‐2‐ 14 C with ethyl orthoformate and 3,4‐methylene‐dioxyaniline in the presence of anhydrous zinc chloride as a catalyst to ethyl α‐carbethoxy‐β‐(3,4‐methylenedioxyanilino) acrylate‐2‐ 14 C (III). The overall radiochemical yield of AB‐206‐3‐ 14 C (I) was 9.6% from methanol‐ 14 C.