Diazonamide Synthetic Studies. Reactivity of N-Unsubstituted Benzofuro[2,3-B]Indolines

Chemistry of Heterocyclic Compounds 2015
Ilga Mutule, Toms Kalniņš, Edwin Vedējs, Edgars Sūna

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 intramol. 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.

Keywords
Diazonamide synthetic studies. Reactivity of N-unsubstituted benzofuro[2,3-b]indolines
DOI
10.1007/s10593-015-1749-7
Hyperlink
http://link.springer.com/article/10.1007%2Fs10593-015-1749-7

Mutule, I., Kalniņš, T., Vedējs, E., Sūna, E. Diazonamide Synthetic Studies. Reactivity of N-Unsubstituted Benzofuro[2,3-B]Indolines. Chemistry of Heterocyclic Compounds, 2015, Vol.51, Iss.7, pp.613-620. ISSN 0009-3122. e-ISSN 1573-8353. Available from: doi:10.1007/s10593-015-1749-7

Publication language
English (en)