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| Title: | Application of primary allyl amines afforded by the Baylis-Hillman adducts for heterocyclic synthesis: Generation of 5-benzyl-4(3H)-pyrimidinones and 2-benzylidene-2,3-dihydro-pyrrolizin-1-ones |
| Authors: | Nag, Somnath
Madapa, Sudharshan
Batra, Sanjay |
| Keywords: | Baylis-Hillman
Formamide
N-formylation
primary allyl amine
4(3H)-pyrimidinone
4-pyridinamine
2,3-dihydro-1H-pyrrolizin-1-one |
| Issue Date: | 2008 |
| Citation: | Synthesis (2008), 101-109 |
| Series/Report no.: | CDRI Communication No. 7367 |
| Abstract: | The applications of the primary allyl amines afforded by the acetyl derivative of Baylis-Hillman adducts of acrylate for the synthesis of heterocycles using robust reactions are described. In the first strategy a one-pot synthesis of 5-benzyl-4(3H)-pyrimidinones have been achieved via N-formylation of the amines in the presence of neat formamide followed by ammonium formate-mediated cyclization. These pyrimidinones have been demonstrated to be excellent precursor to the 4-pyridinamine derivatives. In the second strategy the synthesis of 2-benzylidene-2,3-dihydro-pyrrolizin-1-ones have been accomplished via treatment of allyl amine with dimethoxyfuran followed by saponification and PPA-mediated intramolecular cyclization. |
| URI: | http://hdl.handle.net/123456789/73 |
| Appears in Collections: | Medicinal and Process Chemistry
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| sbatra-7367-SYNTHESIS-2008-101.pdf | | 206Kb | Adobe PDF | View/Open |
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