Abstract
POCl3-induced dehydration of 3,3'-methylenedi(2-arylamino-4H-chromen-4-ones) gives 6,8-diarylimino-7H-pyrano[3,2-c:5,6-c’]dicoumarins, which undergo chemoselective hydrolysis of the imino function to form 7H-pyrano[3,2-c:5,6-c’]dicoumarins by heating with HCl in methanol However, cleavage of the ether function occurs upon heating in acetic acid to give 3,3'-methylenedi(2-arylamino-4H-chromen-4-ones).
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