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1-Alkyl- and (±)-1,2-Dialkyl-2,3-dihydro-1,8-naphthyridin-4(1H)-ones by a Tandem Michael--SNAr Annulation Reaction.
- Source :
-
Journal of Organic Chemistry . 3/1/2013, Vol. 78 Issue 5, p2144-2148. 5p. - Publication Year :
- 2013
-
Abstract
- A tandem Michael--SNAr annulation reaction has been developed for the synthesis of 1-alkyl and (±)-1,2-dialkyl-2,3-dihydro-1,8-naphthyridin-4(1H)-ones. Treatment of 1-(2-chloropyridin-3-yl)prop-2-en-1-one (R = H) or (E or Z)-1-(2-chloropyridin-3-yl)but-2-en-1-one (R = CH3) with R'NH2 in DMF at 50 °C for 24 h provides 2,3-dihydro-1,8-naphthyridin-4(1H)-ones in 65-85% yields. Mechanistic studies suggest that the reaction sequence is initiated by Michael addition to the side chain enone. [ABSTRACT FROM AUTHOR]
- Subjects :
- *NAPHTHYRIDINES
*CARBONYL compounds
*ENOLS
*CHEMICAL reactions
*CHEMICAL processes
Subjects
Details
- Language :
- English
- ISSN :
- 00223263
- Volume :
- 78
- Issue :
- 5
- Database :
- Academic Search Index
- Journal :
- Journal of Organic Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 86231937
- Full Text :
- https://doi.org/10.1021/jo3018632