1326316-03-3

Upstream product

• 226989-36-2 4-hydroxy-1-trityl-1H-pyrazole 
• 358-23-6 trifluoromethylsulfonic anhydride 
• 1326316-23-7 3-allyl-4-hydroxy-2-trityl-2H-pyrazole 
• 1326316-18-0 4-allyloxy-1-trityl-1H-pyrazole 

Downstream Products

• 1326316-05-5 3-(3-hydroxy)propyl-4-trifluoromethanesulfonyloxy-2-trityl-2H-pyrazole 
• 1326316-08-8 3-(3-toluenesulfonyloxy)propyl-4-trifluoromethane sulfonyloxy-2-trityl-2H-pyrazole 
• 1326316-12-4 5,6-dihydro-3-hydroxy-4H-pyrrolo[1,2-b]pyrazole 
• 10183-74-1 withasomnine 
• 1428446-99-4 C₁₂H₁₂N₂O 
• 1428447-00-0 C₁₃H₁₄N₂ 
• 1428447-01-1 C₁₂H₁₁N₃O₂ 
• 1428447-02-2 C₁₂H₁₃N₃ 
• 1428447-04-4 C₁₂H₁₁FN₂ 

Relevant academic research and scientific papers

Divergent synthesis and evaluation of inhibitory activities against cyclooxygenases-1 and -2 of natural withasomnines and analogues

The divergent synthesis of natural withasomnines and analogues was achieved from 4-hydroxypyrazoles, which was prepared via alkaline hydrolysis of the Baeyer-Villiger oxidation products from 4-formylpyrazoles. Key steps of this synthesis are regioselective Claisen rearrangement of 4-allyloxypyrazoles and the Suzuki-Miyaura coupling of 5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl trifluoromethanesulfonate and commercially available arylboronic acids. The Suzuki-Miyaura coupling at the final step of this strategy enabled facile access to natural withasomnines and their analogues. The biological activities of the twelve synthesized compounds against cyclooxygenases-1 and -2 (COX-1 and COX-2) were evaluated.

Divergent synthesis of withasomnines via synthesis of 4-hydroxy-1H- pyrazoles and Claisen rearrangement of their 4-O-allylethers

4-Hydroxypyrazoles were synthesized by the alkaline hydrolysis of the Baeyer-Villiger oxidation products of 4-formylpyrazoles. This new synthesis of 4-hydroxypyrazoles was applied to the divergent synthesis of withasomnine alkaloids in a unique strategy, for which the key steps included the regioselective Claisen rearrangement of their 4-O-allyl-4-hydroxy-1H-pyrazoles and a Suzuki coupling of 4-trifluoromethanesulfonyloxy-1H-pyrazoles and arylboronic acids.