Back to Search Start Over

1-Alkyl- and (±)-1,2-Dialkyl-2,3-dihydro-1,8-naphthyridin-4(1H)-ones by a Tandem Michael--SNAr Annulation Reaction.

Authors :
Bunce, Richard A.
Squires, Scott T.
Nammalwar, Baskar
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]

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