2014
DOI: 10.1016/j.cclet.2014.03.013
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Efficient synthesis of 4-substituted pyrazole via microwave-promoted Suzuki cross-coupling reaction

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Cited by 14 publications
(6 citation statements)
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“…The scope of the Suzuki reaction for synthetic applications (particularly, the syntheses of natural products, biologically active pharmaceuticals, fine chemicals, and polymers for electronic applications) have been surveyed in several excellent reviews. 57,103,147−149 Over the past decade, our group has engaged in pesticide discovery, and we have recently reported the synthesis of bioactive heterocycles, i.e., bulky 4-substituted isatins, 150 functionalized 6-arylsalicylates, 151 6-substituted-thiosalicylates, 152 4-substituted pyrazoles, 153 N-(pyridin-2-ylmethyl) substituent biphenyl-4-sulfonamides, 154 and N-quinolyl biaryl carboxamides, 155 Boscalid 26. The fungicide boscalid 26 (Cantus, Pristine, Figure 5) belongs to the carboxamide (nicotinamide) class of fungicides, was developed by BASF in 2003, and is the most significant member of the SDHI (succinate dehydrogenase inhibitor) group of fungicides.…”
Section: Journal Of Agricultural and Food Chemistrymentioning
confidence: 99%
See 1 more Smart Citation
“…The scope of the Suzuki reaction for synthetic applications (particularly, the syntheses of natural products, biologically active pharmaceuticals, fine chemicals, and polymers for electronic applications) have been surveyed in several excellent reviews. 57,103,147−149 Over the past decade, our group has engaged in pesticide discovery, and we have recently reported the synthesis of bioactive heterocycles, i.e., bulky 4-substituted isatins, 150 functionalized 6-arylsalicylates, 151 6-substituted-thiosalicylates, 152 4-substituted pyrazoles, 153 N-(pyridin-2-ylmethyl) substituent biphenyl-4-sulfonamides, 154 and N-quinolyl biaryl carboxamides, 155 Boscalid 26. The fungicide boscalid 26 (Cantus, Pristine, Figure 5) belongs to the carboxamide (nicotinamide) class of fungicides, was developed by BASF in 2003, and is the most significant member of the SDHI (succinate dehydrogenase inhibitor) group of fungicides.…”
Section: Journal Of Agricultural and Food Chemistrymentioning
confidence: 99%
“…Thus, the reaction is suitable for not only academic laboratories but also industrial processes. The scope of the Suzuki reaction for synthetic applications (particularly, the syntheses of natural products, biologically active pharmaceuticals, fine chemicals, and polymers for electronic applications) have been surveyed in several excellent reviews. ,, Over the past decade, our group has engaged in pesticide discovery, and we have recently reported the synthesis of bioactive heterocycles, i.e., bulky 4-substituted isatins, functionalized 6-arylsalicylates, 6-substituted-thiosalicylates, 4-substituted pyrazoles, N -(pyridin-2-ylmethyl) substituent biphenyl-4-sulfonamides, and N -quinolyl biaryl carboxamides, via microwave-assisted Suzuki cross-couplings. The Suzuki coupling is widely applied in the synthesis of agrochemicals, with the most prominent examples being the synthesis of the fungicides boscalid 26 , bixafen 33 , fluxapyroxad 36 , kresoxim-methyl 41 , and pyriofenone 47 ; the insecticide bifenazate 52 , the herbicide halauxifen-methyl 56 , and the pheromone bombykol 59 .…”
Section: Suzuki Cross-coupling Reactionsmentioning
confidence: 99%
“…35,42 Compound 3a upon the coupling reaction with 2-(4-methoxy-3-(methylsulfonyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 4 , and sodium carbonate in the presence of PdCl 2 (dppf) (10 mole%) in 1,4-dioxane gave 1-(4′-methoxy-3′-(methylsulfonyl)-[1,1′-biphenyl]-4-yl)-5-methyl-3-(trifluoromethyl)-1 H -pyrazole, 5a . 43,44 The synthesis of compounds 5b and 5c was achieved by using (4-iodo-2-methylphenyl)hydrazine ( 2b ) and (4-iodo-2-isobutylphenyl)hydrazine ( 2c ), respectively. Selectively, (4-iodo-2-isobutylphenyl)hydrazine ( 2c ) was used for the derivatization of 1,1,1-trifluoro-5-alkyl-2,4-dione; compounds 5d-g were synthesized under similar experimental conditions (Scheme 1).…”
Section: Resultsmentioning
confidence: 99%
“…It was also 226 determined that the amount of the catalyst has a great influence on 227 the transformation (Table 3, entries 6,[12][13][14], and the best results 228…”
mentioning
confidence: 99%
“…Recently, as a new 13 generation of heterogeneous catalysts for the Suzuki coupling 14 reaction, immobilization of Pd nanoparticles on solid supports has 15 received considerable attention because of their superior catalytic 16 performance, good stability, ease of separation and satisfactory 17 reusability in comparison to the traditional homogeneous cata-18 lysts, such as Pd(OAc) 2 and PdCl 2 [2][3][4][5][6]. Generally, the solid 19 supports, especially carbon nanomaterials such as activated 20 carbon [7], carbon molecular sieve [8], fullerene [9], carbon 21 nanotube [10], nanofiber and graphene [11], have been used as the 22 support for heterogeneous palladium catalysts [12,13].…”
mentioning
confidence: 99%