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| 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 |
| Authors: | Pathak, Richa
Madapa, Sudharshan
Batra, Sanjay |
| Keywords: | Baylis-Hillman
TFA
Claisen rearrangement
3-arylmethyl-3,4-dihydro-1H-quinolin-2-one
2-amino-3-arylmethyl-quinoline |
| Issue Date: | 2007 |
| Citation: | Tetrahedron, 63, 363-370 (2007) |
| Series/Report no.: | CDRI Communication Number 7071 |
| Abstract: | 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. |
| URI: | http://hdl.handle.net/123456789/37 |
| Appears in Collections: | Medicinal and Process Chemistry
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| sbatra-7071-Tetrahedron-2007pub.pdf | | 224Kb | Adobe PDF | View/Open |
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