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

Ilga Mutule, Toms Kalnins, Edwin Vedejs, Edgars Suna
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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


Keywords


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

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