A novel synthesis of indole derivatives via a claisen rearrangement

✍ Scribed by B.S. Thyagarajan; J.B. Hillard; K.V. Reddy; K.C. Majumdar

• Publisher: Elsevier Science
• Year: 1974
• Tongue: French
• Weight: 149 KB
• Volume: 15
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)82615-0

✦ Synopsis

We wish to report a facile thermal rearrangement of an N-aryl propynylamine oxide to an indole. The present study, to our knowledge, is the first report of such a rearrangement.

Compound 1 (89.5%; m.p. 76-77)* was prepared by the condensation of l-(4-chlorophenoxy)-4chloro-2-butyne3 with two moles of N-methylaniline in refluxing n-butanol.

Oxidation of 1. with