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Synthesis of carbon-14labelled antimicrobial agents, I, synthesis of 1,4-dihydro-1-methoxy-6,7-methylenedioxy-4-oxo-quinoline-3-carboxylic-3-14C acid (AB-206-3-14C)

✍ Scribed by A. Yoshitake; Y. Makari; M. Endo

Publisher
John Wiley and Sons
Year
1974
Tongue
French
Weight
291 KB
Volume
10
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

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.

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