Some degradations of calycanthine

✍ Scribed by M. Takamizawa; H. Takahashi; H. Sakakibara; T. Kobayashi

• Book ID: 104202944
• Publisher: Elsevier Science
• Year: 1967
• Tongue: French
• Weight: 319 KB
• Volume: 23
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(01)83349-4

✦ Synopsis

Ah&act~dation

of benzoylcalycanthine 0, yielded calycanine (Bl). Prolonged action of dil. HCI on calycanthine afforded an intermed& product VU, which gave 3-(2'benzoylaminophenyl)-I-methyl-2-pyrroline (VJB) on benzoylation followed by pyrolysis. DitrosocaJycanthine (IX) was converted into its diazonium salt by treatment with cold 4N HCJ, and the latter underwent BUF coupling reactions with phenols.

BARGER~ and

Manskea suggested structures for calycanthine, and in 1954, Robinson and TeuberS proposed one of the /?,/?'-oxidatively coupled structures of two molecules of N-methyltryptamine (Ia). Recently, Woodward'd and Robertson'd groups presented the structure II, determined by means of X-ray analysis. This structure has only 6-membered and no 5-membered rings.