Naslov
In situ formed tert-butyl hypoiodite as an efficient oxidant for rapid, room temperature, metal-free dehydrogenation of Biginelli 3, 4-dihydropyrimidin-2(1H)-ones under basic conditions

Autori
Lesjak Kolarović, Danijela ; Vinković, Vladimir ; Litvić, Mladen

Izvornik
ARKIVOC (1551-7004) 2016 (2016), 3; 271-286

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
dehydrogenation ; 3 ; 4-dihydropyrimidin-2(1H)-ones ; iodine ; tert-butyl hypoiodite

Sažetak
A mild, highly efficient synthetic method was developed for the dehydrogenation of 3, 4- dihydropyrimidin-2(1H)-ones employing in situ formed tert-butyl hypoiodite under basic conditions. The oxidant was prepared by the reaction of molecular iodine and potassium tertbutoxide. The reaction was carried out in dry tetrahydrofuran at room temperature and high purity products were isolated in high yields after simple work-up. The reaction times (3-10 min.) indicated the new method is superior in comparion to other literature oxidants employed under classical conditions or microwave promoted reactions. Two plausible mechanisms of dehydrogenation were proposed and the active species tert-butyl hypoiodite was characterized by UV/Vis spectroscopy method.

Izvorni jezik
Engleski

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