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Indole alkaloid synthesis via Claisen rearrangement. Total synthesis of secodine

✍ Scribed by Raucher, Stanley; Macdonald, James E.; Lawrence, Ross F.


Book ID
120063000
Publisher
American Chemical Society
Year
1981
Tongue
English
Weight
446 KB
Volume
103
Category
Article
ISSN
0002-7863

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A novel synthesis of indole derivatives
✍ B.S. Thyagarajan; J.B. Hillard; K.V. Reddy; K.C. Majumdar πŸ“‚ Article πŸ“… 1974 πŸ› Elsevier Science 🌐 French βš– 149 KB

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