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Novel ring transformation of quinolines to indole derivatives in two steps via 1,4-dihydroquinoline derivatives

✍ Scribed by Michiharu Sugiura; Natsuyo Yamaguchi; Koosuke Asai; Isamu Maeba

Publisher: Elsevier Science
Year: 2003
Tongue: French
Weight: 105 KB
Volume: 44
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(03)01552-1

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✦ Synopsis

Diphenyl 1-phenoxycarbonyl-1,4-dihydroquinoline-4-phosphonates 5c-g, obtained from the reaction of corresponding quinoline derivatives 1 with phenyl chloroformate and triphenyl phosphite in one step, were ozonized in CHCl 3 and CH 3 COOH. Treatment of the resulting mixture with NaHCO 3 produced the 3-formyl-1-phenoxycarbonylindole derivatives 8a-e in high yields. The ring transformation of quinolines 1 to indoles 8 proceeds under mild conditions.

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