Divergent synthesis of 4,6-diarylated pyridin-2(1H)-ones from chalcones: novel access to 2,4,6-triaryl pyridines.
A wide range of 4,6-diarylated/heterylated pyridin-2(1H)-one derivatives were synthesized in good to excellent yields from 1,3-diarylated/heterylated-2-propen-1-ones (chalcones) in one pot under metal and base-free conditions. This domino reaction suggests a novel mechanism comprising of Michael addition followed by amination, subsequent intramolecular amidation and finally dehydronitrosation. The usefulness of the designed 4,6-diarylated/heterylated pyridin-2(1H)-one derivatives has further been demonstrated by synthesizing medicinally important 2,4,6-triaryl/heteryl pyridines via Pd-catalyzed cross-coupling reaction.
Department of Chemistry, University of Jammu, Jammu 180006, India. k2kapoor@yahoo.com.
Rajni
R
Khajuria
Prakash
P
Kannaboina
Kamal K
KK
Kapoor
Annah
A
Gupta
Gaurav
G
Raina
Amanpreet Kaur
AK
Jassal
Love Karan
LK
Rana
Maninder S
MS
Hundal
Parthasarathi
P
Das
D000586:Amination; D002384:Catalysis; D047188:Chalcones / Q000138:chemical synthesis / Q000737:chemistry*; D003500:Cyclization; D008958:Models, Molecular; D010165:Palladium / Q000737:chemistry; D011725:Pyridines / Q000138:chemical synthesis* / Q000737:chemistry
D047188:Chalcones; D011725:Pyridines; D010165:Palladium