Morehead State University
A Study on Ring Closure of Hydroxyfulvenes Using Hydrazines
Institution
Morehead State University
Faculty Advisor/ Mentor
Mark Blankenbuehler
Abstract
The purpose of this experiment is the synthesis of symmetric cyclopeanta[d]-pyridazines via a hydroxyfulvene intermediate product. The experi-ment is done using inert atmosphere using a Schlenk line under Argon. The hydroxyfulvene product is made by combining cyclopentadiene and n-butyl lithium, then adding an acyl halide in order to add the symmetric side groups to the cyclopentadienide anion. After an acid workup the product is extracted with ether, and finally this hydroxyfulvene derivative is combined with a hydrazine benzenesulfonamide to close the ring into the fused pyridazine ring. The hydroxyfulvene and the benzensulfonamide are both characterized using 1H-NMR, IR spectroscopy, and melting points. The overall purpose of this experiment is the potential synthesis of a useful cyclooxygenase inhibitor, in essence an analog of Celebrex®.
A Study on Ring Closure of Hydroxyfulvenes Using Hydrazines
The purpose of this experiment is the synthesis of symmetric cyclopeanta[d]-pyridazines via a hydroxyfulvene intermediate product. The experi-ment is done using inert atmosphere using a Schlenk line under Argon. The hydroxyfulvene product is made by combining cyclopentadiene and n-butyl lithium, then adding an acyl halide in order to add the symmetric side groups to the cyclopentadienide anion. After an acid workup the product is extracted with ether, and finally this hydroxyfulvene derivative is combined with a hydrazine benzenesulfonamide to close the ring into the fused pyridazine ring. The hydroxyfulvene and the benzensulfonamide are both characterized using 1H-NMR, IR spectroscopy, and melting points. The overall purpose of this experiment is the potential synthesis of a useful cyclooxygenase inhibitor, in essence an analog of Celebrex®.