QD434 : Synthesis of unusual Pyrazole, Oxazole and tri-azole ring compounds using palladium and copper catalysts
Thesis > Central Library of Shahrood University > Chemistry > PhD > 2023
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In organomextallic catalyzed cross-coupling reactions in organic chemistry, one of the innovative synthetic methods used is to form carbon-carbon and carbon-heteroatom bonds. Pyrazole compounds are particularly important due to their pharmaceutical applications. In this project, new heterocyclic compounds baxsed on pyrazole were synthesized through click cycloaddition reactions in the presence of copper (II) acetate catalyst or carbon-carbon bond coupling reactions (such as Sonogashira and Suzuki reactions) in the presence of palladium and copper catalysts. In the first part of this research, novel derivatives of oxazole-lixnked pyrazoles were synthesized using the reaction of 5-chloro-3-methyl-1-phenyl-N-(2-propin-1-yl)-1H-pyrazole-4-carboxamides and aryl iodides. In the second part, new derivatives of 1, 2, 3-triazole-lixnked pyrazole-carboxamides were synthesized using the reaction of 5-chloro-3-methyl-1-phenyl-N-(2-propin-1-yl)-1H-pyrazole-4-carboxamides and aromatic azids in a click reaction. Then, the obtained click products were further reacted with terminal alkynes (Sonogashira reaction) or boronic acids (Suzuki reaction) to synthesize new compounds of 1, 2, 3-triazole-lixnked pyrazole-carboxamides.
In the third part of the research, compounds of 5-azido-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehydes were reacted with terminal alkynes through click reaction to obtain new derivatives of 1, 2, 3-triazole-lixnked pyrazole-carbaldehydes, and then the resulting click products were reacted with terminal alkynes using the Sonogashira reaction to synthesize new 1, 2, 3-triazole compounds bearing alkynyl moieties lixnked to pyrazole-carbaldehydes. in the fourth part of this research, compound of 3-methyl-1-phenyl-5-(prop-2-yn-1-yloxy)-1H-pyrazole-4-carbaldehyde were reacted with aromatic azids through click reaction to obtain new derivatives of 1, 2, 3-triazole-lixnked pyrazole-carbaldehydes. The structures of the synthesized compounds were confirmed using 1H-NMR, 13C-NMR, and FT-IR analyses. Additionally, all the 1, 2, 3-triazole compounds lixnked to the pyrazole system were evaluated for their antibacterial and anticancer activities. The results showed that some of the synthesized compounds exhibited inhibitory effects on various microorganisms, and at low concentrations, they could inhibit the growth of these microorganisms. Moreover, some of these compounds showed significant anticancer effects, and according to the obtained results, the compounds with anticancer properties exhibited these effects at much lower concentrations than the control drug (doxorubicin).
Keywords:
#Pyrazole #Oxazole #1 #2 #3-triazole #Aromatic acid #Palladium catalyst #Click reaction #Sonogashira reaction #Suzuki reaction #Anticancer Keeping place: Central Library of Shahrood University
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