24195-02-6Relevant articles and documents
1,6- and 1,7-naphthyridines. II. Synthesis from acyclic precursors
Blanco, M. Mercedes,Perillo, Isabel A.,Schapira, Celia B.
, p. 979 - 984 (1999)
A number of 8-hydroxy-6-methyl-1,6-naphthyridin-5(6H)-one-7- carboxylic acid alkyl esters 3 and the isomeric 5-hydroxy-7- methyl-1,7-naphthyridin-8(7H)-one-6-carboxylic acid alkyl esters 4 were synthesized from acyclic precursors obtained starting from quinolinic anhydride 5. Thus, methanolysis of 5 afforded the hemiester 6 which treated with oxalyl chloride and sarcosine ethyl ester gave 3-(N-ethoxycarbonylmethyl-N- methylcarbamoyl)pyridine-2-carboxylic acid methyl ester 8. Compound 8 was cyclized to naphthyridines 3a-e with sodium alkoxides. The isomeric naphthyridines 4a-c were obtained by cyclization of the open intermediary 2-(N-ethoxycarbonylmethyl-N- methylcarbamoyl)pyridine-3-carboxylic acid methyl ester 9 obtained by a route that involves treatment of 5 with sarcosine ethyl ester and esterification with diazomethane. Spectroscopic properties (1H nmr, uv, ir) of compounds 3 and 4 are discussed and confirmed the proposed structures.
Efficient synthesis of novel pyrido[3,2-d]pyrimidine-2,4-diones
Mamouni,Aadil,Akssira,Lasri,Sepulveda-Arques
, p. 2745 - 2747 (2003)
A series of pyrido[3,2-d]pyrimidine-2,4-diones 5a-g have been synthesized through conversion of 2,3-pyridinedicarboxylic anhydride 1 into half-ester 2, subsequent Curtius rearrangement and further reaction with amino acids.
Convenient Synthesis of 3-(1-carboxyalkyl)pyrido[2,3-d]pyrimidine-2,4-diones
Saoud,Benabdelouahab,El Guemmout,Romerosa
, p. 439 - 444 (2007/10/03)
Cheap and safety synthetic route to obtain 3-(1-carboxyalkyl)pyrido[2.3-d]pyrimidinediones (carboxyalkyl = -CHRCO2H; R = H, 7; CH2 8; CH2Ph, 9; Ph. 10; CH2(C3H3N2, 11; (CH2)2CO2H, 12; CH2CO2H, 13) starting from 2.3-pyridinedicarboxylic acid, 1, is described. A process scheme consistent with empirical observations is proposed.