- Cu-Mediated Expeditious Annulation of Alkyl 3-Aminoacrylates with Aryldiazonium Salts: Access to Alkyl N2-Aryl 1,2,3-Triazole-carboxylates for Druglike Molecular Synthesis
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Alkyl N-aryl 1,2,3-triazole-carboxylates are important molecules or intermediates in medicinal chemistry, but the synthesis of N2-aryl counterparts remains elusive. Herein, we describe a Cu-mediated annulation reaction of alkyl 3-aminoacrylates with aryldiazonium salts, both of which are readily available substrates. Furthermore, alkyl 2-aminoacrylates are also viable substrates. Diverse alkyl N2-aryl 1,2,3-triazole-carboxylates and their analogues can be rapidly prepared under mild conditions. Especially, this protocol allows one to access several druglike variants of carbonic anhydrase inhibitors and celecoxib.
- Liu, Hao-Nan,Cao, Hao-Qiang,Cheung, Chi Wai,Ma, Jun-An
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supporting information
p. 1396 - 1401
(2020/02/22)
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- 1,2,3-Triazole N-Oxides. II. Synthesis of Substituted 4(5)-Ethoxycarbonyl-1,2,3-triazole N-Oxides
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Oxidative cyclization of ethyl 2-hydrazono-3-hydroxyimino- and 3-hydrazono-2-hydroxyiminobutanoates in the presence of γ-MnO2 yields isomeric 4(5)-methyl-2-phenyl-5(4)-ethoxycarbonyl-1,2,3-triazole 1-oxides. Alkaline hydrolysis and ammonolysis
- Kirillova,Shul'gina,Shafeev,Al'mukhamedov,Vereshchagin
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p. 1051 - 1054
(2007/10/03)
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- Methylation of 3-Methyl- and 3-Phenyl-4-arylhydrazonoisoxazol-5-ones with Diazomethane
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3-Methyl(or phenyl)-4-arylhydrazonoisoxazol-5-ones on methylation with diazomethane afford 3-methyl(or phenyl)-4-(N-methylarylhydrazono)isoxazol-5-ones and 3-methyl(or phenyl)-5-methoxy-4-arylhydrazonoisoxazoles.The latter compounds readily rearrange to 4
- Singh, Shyam K.,Summers, Lindsay A.
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p. 933 - 939
(2007/10/02)
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