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Title: Synthesis of novel 6-substitutedaminopyridin-2(H)-ones
Authors: Patel, A K
Patel, N B
Issue Date: Aug-2004
Publisher: NISCAIR-CSIR, India
IPC Code: Int. Cl.7 C 07 D 211/00
Abstract: 6-Substituted-amino-4-( 4-ethoxyphenyl)-1-phenyl pyridin-2(H)ones 4,5 have been prepared from citric acid. It is treated with conc. H2SO4 and then with phenetole to give β-arylglutaconic acid which on fusion with arylaminc results in 4-(4-ethoxyphcnyl)-1 aryl-5-H-pyridine-2,6-diones 2. When 2 (Ar=phenyl) is reacted with phosphorous oxychloride it gives 6-chloro-4-(4-ethoxyphenyl)-1 -phenylpyridin-2(H)-one 3, which on treatment with secondary amines yields 6-substituted-amino-4-(4-ethoxyphenyl)-1 -phenylpyridin- 2(H)-ones 4 and 5. When 4 and 5 are subjected to azo coupling with different aryldiazonium chlorides furnish two isomers 6-substituted-amino-4-(4-ethoxyphenyl)-1-phenyl-3- (arylazo)pyridin -2(H)-ones 6a-j and 7a-j and 6-substituted-amino-4-(4-ethoxyphenyl)-1-phenyl-5-(arylazo)pyridin-2(H)-ones 6k-t and 7k-t. However, the Mannich reaction on 4 and 5 gives only single product identified as 6-substituted-amino-4-(4-ethoxyphenyl)-1-phenyl-3-(aminomethyl)pyridin -2(H)-ones 8a-b and 9a-b. All the compounds have been characterized by elemental analysis, IR and NMR spectral data.
Page(s): 1774-1778
ISSN: 0975-0983(Online); 0376-4699(Print)
Appears in Collections:IJC-B Vol.43B(08) [August 2004]

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