Trifluoroacetic acid: A more effective and efficient reagent for the synthesis of 3-arylmethylene-3,4-dihydro-1H-quinolin-2-ones and 3-arylmethyl-2-amino quinolines from Baylis-Hillman derivatives via Claisen rearrangement
IR@CDRI: CSIR-Central Drug Research Institute, Lucknow
View Archive Info| Field | Value | |
| Creator |
Pathak, Richa
Madapa, Sudharshan Batra, Sanjay |
|
| Date |
2007-12-07T07:09:44Z
2007-12-07T07:09:44Z 2007 |
|
| Identifier |
Tetrahedron, 63, 363-370 (2007)
http://hdl.handle.net/123456789/37 |
|
| Description |
Trifluoroacetic acid has been discovered to be a highly effective and efficient reagent for the tandem Claisen rearrangement and cyclisation reaction to yield 3-arylmethylene-3,4-dihydro-1H-quinolin-2-ones from compounds obtained from the SN2 reaction between anilines and acetyl derivatives of Baylis-Hillman adducts of acrylates in the presence of DABCO. In contrast similar compounds obtained from the acetyl derivatives of Baylis-Hillman adduct of acrylonitrile on treatment with trifluoroacetic acid directly furnish 3-arylmethyl-2-amino-quinoline via tandem Claisen rearrangement, cylisation and isomerisation.
|
|
| Format |
229498 bytes
application/pdf |
|
| Language |
en
|
|
| Relation |
CDRI Communication Number 7071
|
|
| Subject |
Baylis-Hillman
TFA Claisen rearrangement 3-arylmethyl-3,4-dihydro-1H-quinolin-2-one 2-amino-3-arylmethyl-quinoline |
|
| Title |
Trifluoroacetic acid: A more effective and efficient reagent for the synthesis of 3-arylmethylene-3,4-dihydro-1H-quinolin-2-ones and 3-arylmethyl-2-amino quinolines from Baylis-Hillman derivatives via Claisen rearrangement
|
|
| Type |
Article
|
|