Coumarin derivatives and method for synthesizing 5'-methyl psoralens therefrom
AssigneeThe Regents of the University of California
InventorsDean R. Bender, John E. Hearst, Henry Rapoport
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Abstract
Two species of a coumarin derivative are disclosed, both of which may be produced from a 7-hydroxycoumarin precursor. The one species is an oxime and the other is a .beta.-haloallyl ester. A method for making a psoralen compound in high yield comprises treating these coumarin derivatives with an acid to fuse a furan ring thereto, and recovering a 5'-methyl psoralen therefrom. The 5'-methyl psoralen may be produced in up to about 70% overall yield with respect to the 7-hydroxycoumarin precursor.
Claims10
A method for making a psoralen compound comprising the steps of:
- prioviding a coumarin derivative of the structure ##STR13## wherein R.sub.1 ' is --H or --CH.sub.3, R.sub.2 ' is --CH.sub.3, --OCH.sub.3, ##STR14## and X is a halogen;
- treating said coumarin derivative with sulfuric acid, a concentration of said sulfuric acid being from about 70% to about 80%, the treating being at a temperature of from about 0.degree. to about 25.degree. C.;
- and
- recovering a product compound from the treating step, said product compound being a 5'-methyl psoralen having the structure ##STR15##
A method for making a psoralen compound comprising the steps of:
- alkylating a quantity of 7-hydroxy-coumarin with an alkylating agent, said alkylating agent having a halogen, to form a .beta.-haloallyl ether coumarin;
- heating said .beta.-haloallyl ether coumarin in the presence of an acetic anhydride to produce a coumarin derivative of the structure ##STR16## wherein R.sub.1 ' is --H or --CH.sub.3, R.sub.2 ' is --CH.sub.3, --OCH.sub.3, ##STR17## and X is a halogen;
- treating said coumarin derivative with sulfuric acid, a concentration of said sulfuric acid being not greater than about 85%, the treating being at a temperature of from about 0.degree. C. to about 25.degree. C., to form a 5'-methyl psoralen of the structure ##STR18##
Dependencies are inferred from the claim text.