Synthesis, properties, and oxidizing ability of 9,11-dimethylbenzocyclohepta[6,7-b]pyrimido[5,4-d]furan- 10(9H),12(11H)-dionylium tetrafluoroborate |
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Authors: | Naya Shin-ichi Tokunaka Takeshi Nitta Makoto |
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Institution: | Department of Chemistry, School of Science and Engineering, Waseda University, Shinjuku-ku, Tokyo 169-8555, Japan. |
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Abstract: | Convenient preparation of novel 9,11-dimethylbenzocyclohepta6,7-b]pyrimido5,4-d]furan-10(9H),12(11H)-dionylium tetrafluoroborate 11*BF4- consisted of a condensation reaction of benzod]tropone with dimethylbarbituric acid and following oxidative cyclization reaction by using DDQ-Sc(OTf)3 or photoirradiation under aerobic conditions. Alternative synthesis of 11*BF4- was also accomplished by a condensation reaction of 2-methoxybenzod]tropone with dimethylbarbituric acid and a subsequent cyclization reaction by using 42% aq HBF4. The X-ray crystal analysis and MO calculation were carried out to clarify the structural characteristics. Properties of the cation 11 were studied by the pKR+ value (4.7) and reduction potentials (-0.46 and -1.07 V vs Ag/AgNO3) as well as the reaction with some nucleophiles. The oxidizing ability of 11*BF4- toward alcohols in the autorecycling process was demonstrated as well. |
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