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MICROWAVE-INDUCED, SOLVENT-FREE TRANSFORMATIONS OF BENZOHETERACYCLANONES BY HTIB (KOSER'S REAGENT)
Citation:
Patonay, T., A. Levai, E. Riman, AND R S. Varma*. MICROWAVE-INDUCED, SOLVENT-FREE TRANSFORMATIONS OF BENZOHETERACYCLANONES BY HTIB (KOSER'S REAGENT). K. Turnbull (ed.), AMERICAN BEE JOURNAL. Dadant and Sons, Hamilton, IL, 2004(vii):183-195, (2004).
Description:
The microwave-activated reaction of [hydroxy(tosyloxy)iodo]benzene (HTIB) with various chromanones, thiochromanones and dihydroquinolones under solvent-free conditions has been studied. In addition to the common dehydrogenation, 2,3-migration has also been observed in the case of flavanone and 2,2-disubstituted chromanones. 3-Tosyloxychromanones were isolated from the reaction of chromanone and 2-methylchromanone for the first time. Substrates with nucleophilic heteroatoms such as thiochromanones and 2-phenyl-2,3-dihydro-4-quinolone reacted by electrophilic attack at the heteroatom.