Study of the reaction of (Z)-5-bromo-3-(1-methylpyrrolidin-2- ylidene)-3H-indole with pentane-2,4-dione

Authors

  • Masomeh Aghazadeh Department of Chemistry, Faculty of Science, Urmia University, Urmia 57153-165, Iran.
  • Mehdi M. Baradarani Department of Chemistry, Faculty of Science, Urmia University, Urmia 57153-165, Iran.
  • Madeleine Helliwell Helliwell School of Chemistry, Manchester University, Manchester M13 9PL, UK.
  • John A. Joule School of Chemistry, Manchester University, Manchester M13 9PL, UK.

Abstract

The reaction of (Z)-5-bromo-3-(1-methylpyrrolidin-2-ylidene)-3H-indole with refluxing pentane-2,4-dione gave two compounds, the major product, 1-[(E)-4-(5-bromo-1H-indol-3-yl)-1-methyl-2,5,6,7-tetrahydro-1H-azepin-2-ylidene]propan-2-one being accompanied by 1-(7-(2-amino-5-bromophenyl)-1,4-dimethylindolin-5-yl)ethanone. Each product is believed to be derived from initial protonation of (Z)-5-bromo-3-(1-methylpyrrolidin-2-ylidene)-3H-indole by the diketone followed with nucleophilic diketone-C-3- addition at the C-2 of the 3H-indolium cation.

References

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Published

2011-09-09

Issue

Vol. 1 No. 3 (2011)

Section

Organic Chemistry

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