Synthesis of a potential camptothecin intermediate | Zendy

Kametani Tetsuji | Zendy; Takeda Hiromitsu | Zendy; Satoh Fumio | Zendy; Takano Seiichi | Zendy

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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).

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