DIAZONAMIDE SYNTHETIC STUDIES. REACTIVITY OF <i>N</i>-UNSUBSTITUTED BENZOFURO[2,3-<i>b</i>]INDOLINES

Authors

  • Ilga Mutule Latvian Institute of Organic Synthesis, 21 Aizkraukles St., Riga LV-1006, Latvia
  • Toms Kalnins Latvian Institute of Organic Synthesis, 21 Aizkraukles St., Riga LV-1006, Latvia
  • Edwin Vedejs Latvian Institute of Organic Synthesis, 21 Aizkraukles St., Riga LV-1006, Latvia
  • Edgars Suna Latvian Institute of Organic Synthesis, 21 Aizkraukles St., Riga LV-1006, Latvia

DOI:

https://doi.org/10.1007/2527

Keywords:

diazonamide, DMAP, hemiaminal, indole, 3H-indoline

Abstract

Benzofuro[2,3-b]indolines undergo ring opening in the presence of base to generate 3H-indolines. The latter can rearrange into 3-arylindoles through an intramolecular transfer of the methoxycarbonyl moiety from quaternary carbon to oxygen of phenol. The intermediate 3H-indolines can be isolated upon DMAP-catalyzed O-acylation of the phenol moiety with Boc2O.

How to Cite
Mutule, I.; Kalnins, T.; Vedejs, E.; Suna, E. Chem. Heterocycl. Compd. 2015, 51, 613. [Khim. Geterotsikl. Soedin. 2015, 51, 613.]

For this article in the English edition see DOI 10.1007/s10593-015-1749-7

Author Biographies

Ilga Mutule, Latvian Institute of Organic Synthesis, 21 Aizkraukles St., Riga LV-1006, Latvia

Ilga Mutule

Toms Kalnins, Latvian Institute of Organic Synthesis, 21 Aizkraukles St., Riga LV-1006, Latvia

Toms Kalnins

Edwin Vedejs, Latvian Institute of Organic Synthesis, 21 Aizkraukles St., Riga LV-1006, Latvia

Edwin Vedejs

Edgars Suna, Latvian Institute of Organic Synthesis, 21 Aizkraukles St., Riga LV-1006, Latvia

Edgars Suna

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Published

2015-07-31

Issue

Vol. 51 No. 7 (2015)

Section

Original Papers