115705-52-7Relevant academic research and scientific papers
Synthesis and Electrochemistry of Pyrimidoquinazoline-5,10-diones. Design of Hydrolytically Stable High Potential Quinones and New Reductive Alkylation Systems
Skibo, Edward B.,Gilchrist, James H.
, p. 4209 - 4218 (2007/10/02)
The synthesis of pyrimidoquinazoline-5,10-diones 1 and pyrimidoquinazoline-5,10-diones 2 was carried out in conjunction with the design of both hydrolytically stable high potential quinones and new purine-like reductive alkylators.These systems consist of a benzoquinone ring bearing two fused pyrimidin-4(3H)-one rings.The fused pyrimidinone rings serve to protect 1 and 2 from hydrolysis as well as to raise quinone redox potentials by stabilizing the hydroquinones with internal hydrogen bonds (65 mV increase per hydrogen bond).Synthesis of 1 and 2 involved pyrimidinone ring annelation to a 2,5-diamino-3-nitroterephthalic acid derivative and to a 2,4-diamino-1,5-dicarboxy-3-nitrobenzene derivative, respectively.The synthetic studies provided insights into the electronic effects of nitro and amino groups on the annelation process.
