548475-63-4

Upstream product

• 100-53-8 phenylmethanethiol 
• 769-42-6 1,3-dimethylbarbituric acid 
• 3839-48-3 2-chlorotropone 
• 548475-68-9 5a,7-dihydro-7,9-dimethyl-5a-methoxycyclohepta[b]pyrimido[5,4-d]furan-8(7H),10(9H)-dione 
• 548475-44-1 1,3-dimethyl-5-(1'-oxocycloheptatrien-2'-yl)-pyrimidine-2(1H),4(3H),6(5H)-trione 
• 548475-60-1 5-(2'-diethylaminocyclohepta-2',4',6'-trienylidene)pyrimidine-2(1H),4(3H),6(5H)-trione 

Relevant academic research and scientific papers

Novel synthesis and properties of 7,9-dimethylcyclohepta[b]pyrimido[5,4-d]furan-8(7H),10(9H)-dionylium tetrafluoroborate: Autorecycling oxidation of some alcohols under photo-irradiation

Three-step reactions starting from 2-chlorotropone with barbituric acid afforded novel 7,9-dimethylcyclohepta[b]pyrimido[5,4-d]furan-8(7H),10(9H)-dionylium tetrafluoroborate (9·BF4-), which is the isoelectronic compound of the 5-ethyl-3-methyllumiflavinium ion. The stability of cation 9 is expressed by the pKR+ value, which was determined spectrophotometrically, as ca. 6.0. The electrochemical reduction of 9 exhibited low reduction potential at -0.58 (V vs Ag/AgNO3), upon cyclic voltammetry (CV). In a search for the reactivity, reactions of 9·BF4- with some nucleophiles, hydroxide, hydride, amines, thiols, and methanol, were carried out to exhibit that the introduction of nucleophiles is dependent on the nucleophile itself. The photo-induced oxidation reactions of some alcohols catalyzed by 9·BF4- under aerobic conditions were carried out to give the corresponding carbonyl compounds in more than 100% yield [based on compound 9·BF4-], suggesting the oxidizing function of 9·BF4- toward alcohols in the autorecycling process. The UV-vis and fluorescence spectra of 9 were studied to suggest the electron transfer from alcohols to the excited 9.