AI Article Synopsis
- Indol-2-ylmethyl carbanions, when stabilized by specific groups (alkoxycarbonyl, cyano, or benzenesulfonyl), can react with nitroarenes to create σ-adducts.
- In the presence of a base like triethylamine or DBU and trimethylchlorosilane, these σ-adducts undergo further transformation.
- This process results in the formation of indolo[3,2-]quinoline derivatives, achieving moderate to good yields.
Article Abstract
Indol-2-ylmethyl carbanions stabilized by alkoxycarbonyl, cyano or benzenesulfonyl groups react with nitroarenes to form σ-adducts, which in the presence of base (triethylamine or DBU) and trimethylchlorosilane transform into indolo[3,2-]quinoline derivatives in moderate to good yields.
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| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC5789443 | PMC |
| http://dx.doi.org/10.3762/bjoc.14.14 | DOI Listing |
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Similar Publications
Transition-metal-free [3 + 3] annulation of indol-2-ylmethyl carbanions to nitroarenes. A novel synthesis of indolo[3,2-]quinolines (quindolines).
Beilstein J Org Chem
January 2018
Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland.
Article Synopsis
- Indol-2-ylmethyl carbanions, when stabilized by specific groups (alkoxycarbonyl, cyano, or benzenesulfonyl), can react with nitroarenes to create σ-adducts.
- In the presence of a base like triethylamine or DBU and trimethylchlorosilane, these σ-adducts undergo further transformation.
- This process results in the formation of indolo[3,2-]quinoline derivatives, achieving moderate to good yields.
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