- 1,6- and 1,7-naphthyridines. II. Synthesis from acyclic precursors
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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.
- Blanco, M. Mercedes,Perillo, Isabel A.,Schapira, Celia B.
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- Convenient synthesis of 3-(1-carboxyalkyl)pyrido-[2,3-d]pyrimidine-2,4-diones
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A cheap and safe synthetic route to obtain 3-(1-carboxyalkyl)pyrido[2,3-d]pyrimidinediones (carboxyalkyl = -CHRCO2H; R = H; CH2; CH2Ph: Ph; CH2 (C3H3N2); (CH2)2CO2H; CH2CO2H) starting from 2,3-pyridinedicarboxylic acid is described. A process scheme consistent with empirical observations is proposed.
- Saoud,Benabdelouahab,Guemmout, F. El,Romerosa
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- Efficient synthesis of novel pyrido[3,2-d]pyrimidine-2,4-diones
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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.
- Mamouni,Aadil,Akssira,Lasri,Sepulveda-Arques
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- SUBSTITUTED HETEROCYCLES AND THEIR USE AS CHK1, PDK1 AND PAK INHIBITORS
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This invention relates to novel compounds of Formula (I) and to their pharmaceutical compositions and to their methods of use. These novel compounds possess CHK1 kinase inhibitory activity, PDK1 inhibitory activity and Pak kinase inhibitory activity and are accordingly useful in the treatment and/or prophylaxis of cancer.
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Page/Page column 129
(2008/06/13)
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- Convenient Synthesis of 3-(1-carboxyalkyl)pyrido[2,3-d]pyrimidine-2,4-diones
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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.
- Saoud,Benabdelouahab,El Guemmout,Romerosa
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p. 439 - 444
(2007/10/03)
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- Benzopyridazinone and pyridopyridazinone compounds
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Benzo or pyridopyridazinones and pyridazinthiones of the formula STR1 wherein: X and Y are nitrogen or carbon, provided that at least one is carbon, and Z is oxygen or sulfur; R1 is hydrogen, lower alkyl, aryl, aralkyl, heterocyclo, heterocyclo lower-alkyl, heteroaryl, or heteroaralkyl; R2, R3, R4, R5 and R6 are independently selected from hydrogen, lower alkyl, halo, carboxy, alkoxycarbonyl, carbamoyl, lower-alkyl carbonyl, halocarbonyl, thiomethyl, trifluoromethyl, cyano or nitro; or a pharmaceutically acceptable ester, ether or salt thereof, have been found to be useful as an anti-inflammatory, antasthmatic, immunosuppressive, anti-allograft rejection, anti-graft-vs-host rejection, autoimmune disease or analgetic agent(s).
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- Synthesis of the Pyridine Analogues of Phthalide
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Routes for the preparation of the four isomeric pyridine analogues of phthalide are described starting from the readily available pyridine 2,3- and 3,4-diacids, or derivatives, and making use of the differential reactivity of substituents at pyridine 2- versus 3- and 3- versus 4-positions.
- Ashcroft, William R.,Beal, Michael G.,Joule, John A.
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p. 3012 - 3015
(2007/10/02)
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