94158-08-4Relevant articles and documents
Regioselective N-Alkylation of Ethyl 4-Benzyloxy-1,2,3-triazolecarboxylate: A Useful Tool for the Synthesis of Carboxylic Acid Bioisosteres
Sainas, Stefano,Pippione, Agnese C.,Giraudo, Alessandro,Martina, Katia,Bosca, Federica,Rolando, Barbara,Barge, Alessandro,Ducime, Alex,Federico, Antonella,Grossert, Stuart J.,White, Robert L.,Boschi, Donatella,Lolli, Marco L.
, p. 501 - 519 (2019/01/04)
Acidic 4-hydroxy-1,2,3-triazole is a proven bioisostere of acidic functions that has recently been used to replace the acidic moieties of biologically active leads. Straightforward chemical strategies for the synthesis of the three possible N-alkylated 4-hydroxy-1,2,3-triazole regioisomers have been designed and reported herein, by identifying the optimal conditions under which the alkylation of ethyl 4-benzyloxy-1,2,3-triazolecarboxylate (compound 19) can be regiodirected to the triazole N(b) position and thus produce the only isomer that cannot be obtained via the cycloaddition reaction. Furthermore, an innovative platform for parallel synthesis, called Arachno and which has been patented by the authors' group, has been used to speed up the process, and an NMR study has been carried out to better understand the reactivity of compound 19 towards the N(b) position. A library of benzyloxy protected 4-hydroxy-1,2,3-triazoles has been prepared using the two strategies: regiodirection for the N(b) and N(c) isomers and cycloaddition for the N(a) isomers; the processes are described herein. The three N-alkylated regioisomer series have been characterized spectroscopically (NMR and MS). The subsequent catalytic hydrogenation of the 4-benzyloxy protective group on the N-alkylated-4-benzyloxy-5-ethoxycarbonyl-1,2,3-triazoles provided the corresponding substituted 4-hydroxy-1,2,3-triazoles.
Bicyclic Pyrimidine Compounds
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Paragraph 0260; 0261; 0262, (2014/07/23)
The present invention provides compounds of the Formula I: wherein X is a bond or CH2; R is selected from the group consisting of R1 and R2 are each independently selected from the group consisting of CH and N; R3 is H or CH3; R4 is H or CH3; L is selected from the group consisting of —O(CH2)3—, —C(O)NH(CH2)2—, —CH2C(O)NH(CH2)2—, —(CH2)3N(C(O)CH3)CH2—, —(CH2)2N(C(O)CH3)CH2—, —(CH2)3NH—, (CH2)2OCH2—, —(CH2)4—, —(CH2)2NHCH2—, —(CH2)3O—, and —CH2O(CH2)2—; or a pharmaceutically acceptable salt thereof. Compounds of this invention are autotaxin inhibitors.
Transaminations of Enaminones: A Synthesis of Tricyclic, N-Aryl, 1,2,3-Triazole-fused Pyridones
Chan, Tze-Ming,Friary, R.,Jones, H.,Schwerdt, J. H.,Seidl, V.,et al.
, p. 1135 - 1142 (2007/10/02)
1-Phenylmethyl- and 1-(4-methoxyphenylmethyl)-5-chloro-1,2,3-triazole-4-carbonyl chlorides acylated the pyrrolidine enamines of cyclopentanone and cyclohexanone, and the resulting enaminones underwent transaminations with aryl amines under acidic conditions.The products then cyclized under basic conditions to linearly fused, tricyclic 3-phenylmethyl- and 3-(4-methoxyphenylmethyl)-4-aryl-8-oxo-4,5,6,7-tetrahydrocyclopenta-1,2,3-triazolopyridines, and to 5,6,7,8-tetrahydro-4-aryl-3H-1,2,3-triazoloquinolin-9(4H)-ones.Similar transaminations afforded the related 8-phenyl- and 8-(3-chlorophenyl)-1,5,7,8-tetrahydro-1-(phenylmethyl)-4H-thieno-1,2,3-triazolopyridin-4-ones.Phase-transfer and catalytic hydrogenolyses of some of these intermediates furnished 4-aryl-8-oxo-4,5,6,7-tetrahydrocyclopenta-1,2,3-triazolopyridines and 4-aryl-5,6,7,8-tetrahydro-3H-1,2,3-triazoloquinoline-9(4H)-ones.The 3-(4-methoxyphenylmethyl)-4-aryl intermediates were sterically crowded.Two protons from the methoxyphenylmethylphenylmethylgroups were dramatically shielded because of anisotropic effects exerted by the 4-aryl substituents.