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Synthesis of some 3 aryl 5 methoxy 7 methyl iso coumarins



Synthesis of some 3 aryl 5 methoxy 7 methyl iso coumarins



Indian Journal of Chemistry Section B Organic Chemistry Including Medicinal Chemistry 16(11): 1034-1036



Phenol, anisole, o-cresol, m-cresol and p-cresol were condensed with 6-methoxy-4-methylhomophthalic acid in the presence of polyphosphoric acid to give 3-(4'-hydroxyphenyl), 3-(4'-methoxyphenyl), 3-(4'-hydroxy-3'-methylphenyl), 3-(2'-hydroxy-4'-methylphenyl) and 3-(2'-hydroxy-5'-methylphenyl)-5-methoxy-7-methylisocoumarins. On treatment with aqueous NaOH, the respective .omega.-(2'-carboxy-4'-methyl-6'-methoxyphenyl)acetophenones are formed. Sodium borohydride reduction gives the corresponding dihydroisocoumarins which could be transformed into the parent isocoumarins by treatment with NBS [N-bromosuccinimide] followed by refluxing in pyridine. The isocoumarins were characterized as 1-(2H)-isoquinolones.

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