Total Synthesis of Pyrrolnitrin. X. Synthesis of Pyrrolnitrin. (2)

Total Synthesis of Pyrrolnitrin. X. Synthesis of Pyrrolnitrin. (2)

Conversion of 2, 5-disubstituted-3-arylpyrrole (II) to pyrrolnitrin (Ia) and the related compounds (I) was investigated. II was transformed by chlorination followed by hydrolysis and oxidation to 3-aryl-4-chloro-2, 5-pyrroledicarboxylic acids (IV), which were decarboxylated to I in sulfuric acid. Di...

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Veröffentlicht in:Chemical & pharmaceutical bulletin 1969/03/25, Vol.17(3), pp.622-628
Hauptverfasser: TANAKA, KUNIHIKO, KARIYONE, KAZUO, UMIO, SUMINORI
Format: Artikel
Sprache:eng
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Zusammenfassung:Conversion of 2, 5-disubstituted-3-arylpyrrole (II) to pyrrolnitrin (Ia) and the related compounds (I) was investigated. II was transformed by chlorination followed by hydrolysis and oxidation to 3-aryl-4-chloro-2, 5-pyrroledicarboxylic acids (IV), which were decarboxylated to I in sulfuric acid. Dialkyl 3-aryl-4-chloro-2, 5-pyrroledicarboxylate (XI), alkyl β-aryl-4-chloropyrrolecarboxylates and halfesters of IV afforded Ia directly, when heated in sulfuric acid.
ISSN:0009-2363
1347-5223
DOI:10.1248/cpb.17.622