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Synthesis of a potential camptothecin intermediate
Author(s) -
Kametani Tetsuji,
Takeda Hiromitsu,
Satoh Fumio,
Takano Seiichi
Publication year - 1973
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570100117
Subject(s) - chemistry , quinoline , decarboxylation , camptothecin , hydrolysis , condensation , methyl acrylate , medicinal chemistry , organic chemistry , stereochemistry , catalysis , physics , polymer , copolymer , thermodynamics
Condensation of dimethyl 1,2‐dihydro‐2‐oxopyridine‐4,6‐dicarboxylate (IIIb) with methyl acrylate yielded 1,2,3,5‐tetrahydro‐2,7‐dimethoxycarbonyl‐1,5‐dioxoindolizine (IV), which on hydrolysis and decarboxylation gave 1,2,3,5‐tetrahydro‐1,5‐dioxoindolizine‐7‐carboxylic acid (VI). Friedländer condensation of VI with 2‐aminobenzaldehyde, followed by esterification of the resulting oxoindolizino[1,2‐ b ]quinoline‐7‐carboxylic acid (VIIa), yielded a potential camptothecin intermediate 9,10‐dihydro‐7‐methoxycarbonyl‐9‐oxoindolizino[1,2‐ b ]quinoline (VIIb).