A facile [hydroxy(tosyloxy)iodo]benzene mediated synthesis of 2-arylimidazo[1,2-<i><img src='/image/spc_char/alpha.gif' border=0></i>]pyrimidines and their conversion into 3-bromo-2-arylimidazo[1,2-<i><img src='/image/spc_char/alpha.gif' border=0></i>]pyrimidines

Abstract

<img src='/image/spc_char/alpha.gif' border=0>-Tosyloxyketone <b style="">2</b>, obtained through hypervalent iodine oxidation of enolizable ketones using [hydroxy(tosyloxy)iodo]benzene (HTIB) in acetonitrile, on treatment with 2-aminopyrimidine <b style="">3</b> generates regioselectively 2-arylimidazo[1,2-<i><img src='/image/spc_char/alpha.gif' border=0> </i>]pyrimidine <b style="">6</b> which upon subsequent treatment with bromine undergoes electrophilic substitution at position-3 to yield 3-bromo-2-arylimidazo[1,2-<i><img src='/image/spc_char/alpha.gif' border=0> </i>]pyrimidine <b style="">8</b>.