Syntheses of 2-alkylamino- and 2-dialkylamino-4,6-diarylpyridines and 2,4,6-trisubstituted pyrimidines using solid-phase-bound chalcones.
Several substituted 2- and 4-hydroxyacetophenones are linked to Wang resin via a modified Mitsunobu protocol. These resin-bound acetophenones are condensed with aromatic aldehydes, and the resulting chalcones 5 are used for the synthesis of 2-dialkylamino- (9a-d) and 2-alkylamino-4,6-diarylpyridines (11a-f), and 2-alkyl-4,6-diaryl- (14a) and 2,4,6-triarylpyrimidines (14b,c) in a manner suitable for combinatorial applications.
Katritzky
A R
AR
Department of Chemistry, University of Florida, Gainesville 32611-7200, USA.
Serdyuk
L
L
Chassaing
C
C
Toader
D
D
Wang
X
X
Forood
B
B
Flatt
B
B
Sun
C
C
Vo
K
K
D000098:Acetophenones; D000447:Aldehydes / Q000138:chemical synthesis; D002599:Chalcone / Q000737:chemistry*; D007202:Indicators and Reagents; D011725:Pyridines / Q000138:chemical synthesis*; D011743:Pyrimidines / Q000138:chemical synthesis*; D012116:Resins, Plant
D000098:Acetophenones; D000447:Aldehydes; D007202:Indicators and Reagents; D011725:Pyridines; D011743:Pyrimidines; D012116:Resins, Plant; D002599:Chalcone