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Iso coumarins 3. synthesis of methyl di hydro iso coumarins and methylenedioxy di hydro iso coumarins and a new synthesis of racemic 5 methyl mellein



Iso coumarins 3. synthesis of methyl di hydro iso coumarins and methylenedioxy di hydro iso coumarins and a new synthesis of racemic 5 methyl mellein



Indian Journal of Chemistry Section B Organic Chemistry Including Medicinal Chemistry 19(1): 9-12



o-Lithio-N-methylbenzamide, upon condensation with propylene oxide, gives 3-methyldihydroisocoumarin. Similarly o-lithio-N-methyl-p-toluamide, upon condensation with ethylene oxide and propylene oxide, gives 6-methyl- and 3,6-dimethyl-dihydroisocoumarins. A similar condensation of o-lithio-N-methyl-m-toluamide with ethylene oxide gives 5-methyldihydroisocoumarin but condensation with propylene oxide gives 3,5-dimethyl- and 3,7-dimethyl-dihydroisocoumarins. The method was used to synthesize (.+-.)-5-methylmellein. The synthesis of 5,6-methylenedioxydihydroisocoumarins from o-lithio-N-methylpiperonylamide is also described. 3-Methyl-6,7-methylenedioxydihydroisocoumarin was synthesized by an acid-catalyzed cyclization reaction. [The dihydroisocoumarins are common, naturally-occurring compounds.].

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