Abstract
The Knoevenagel condensation of 1-substituted 4,4,4-trifluorobutan-1,3-diones with paraformaldehyde in the presence of cyclic and linear 1,3-dienes leads to Diels-Alder cycloadducts via in situ formation of the appropriate 2-methylene-1,3-dicarbonyl compounds 2(a-c). In the reactions with linear 1,3-dienes, compounds 2(a-c) react as dienophiles. In the case of the reactions with cyclic 1,3-dienes both normal and inverse demand Diels-Alder reactions take place.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 6549-6556 |
| Number of pages | 8 |
| Journal | Tetrahedron |
| Volume | 56 |
| Issue number | 35 |
| DOIs | |
| State | Published - Aug 25 2000 |
Funding
The research described in this publication was supported by Russian Fundamental Investigation Foundation (Grant No. 00-03-32760a). The authors express their gratitude to Pissarev S.A. for the assistance in the computation.
Keywords
- 2-methylene-1,3-dicarbonyl compounds
- Diels-Alder reaction
- Hetero-dienes
- Trifluoromethyl ketones
- α,β-unsaturated ketones
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry