2014
DOI: 10.1055/s-0034-1378660
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Synthesis of 1,3,5-Trisubstituted Pyrazoles by the Cope-Type Hydroamination of 1,3-Dialkynes with Alkylhydrazines

Abstract: An efficient method to synthesize 1,3,5-trisubstituted pyrazoles was developed. The reaction of 1,3-dialkynes with alkylhydrazines smoothly proceeded in dimethyl sulfoxide under suitable heating conditions to produce 1,3,5-trisubstituted pyrazoles in satisfactory to excellent yields. 1,3,5-Trisubstituted pyrazoles are important building blocks in the pharmaceutical industry because of their anticancer, 1 antibacterial, 2 analgesic, 3 and anti-inflammatory activities. 4 For example, 1,3,5-trisubstituted pyrazol… Show more

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Cited by 18 publications
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“…In addition to the examples just commented upon, Bertrand and colleagues successfully achieved the catalytic hydroamination of 1,4-diphenylbuta-1,3-diyne with parent ammonia and hydrazine to afford the N-unsubstituted pyrrole 65 [94] and the pyrazole derivative 67 [95], respectively, employing the cationic gold(I) complexes 64 and 66 having a bulky cyclic (alkyl)(amino)carbene ligand (Scheme 37). Within this context, we must mention that access to substituted pyrazoles through metal-free Cope-type hydroamination of 1,3-diynes with hydrazine derivative H 2 NNHR (R = H, alkyl or aryl group) under thermal or base-promoted conditions has been amply reported [96][97][98][99][100][101][102]. Similarly, catalyst-free protocols for the construction of isoxazole [96,100,101,103,104] and pyrimidine [105][106][107] scaffolds by Cope-type hydroamination of 1,3-diynes with hydroxylamine and guanidines, respectively, can also be found in the literature.…”
Section: Hydroamination and Hydroamidation Processesmentioning
confidence: 99%
“…In addition to the examples just commented upon, Bertrand and colleagues successfully achieved the catalytic hydroamination of 1,4-diphenylbuta-1,3-diyne with parent ammonia and hydrazine to afford the N-unsubstituted pyrrole 65 [94] and the pyrazole derivative 67 [95], respectively, employing the cationic gold(I) complexes 64 and 66 having a bulky cyclic (alkyl)(amino)carbene ligand (Scheme 37). Within this context, we must mention that access to substituted pyrazoles through metal-free Cope-type hydroamination of 1,3-diynes with hydrazine derivative H 2 NNHR (R = H, alkyl or aryl group) under thermal or base-promoted conditions has been amply reported [96][97][98][99][100][101][102]. Similarly, catalyst-free protocols for the construction of isoxazole [96,100,101,103,104] and pyrimidine [105][106][107] scaffolds by Cope-type hydroamination of 1,3-diynes with hydroxylamine and guanidines, respectively, can also be found in the literature.…”
Section: Hydroamination and Hydroamidation Processesmentioning
confidence: 99%