Method of preparing sulfmonamides from sulfones
AssigneeG. D. Searle & Co.
InventorsHorng-Chih Huang, Scott R. Harring
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Abstract
A one-pot synthesis of sulfonamides from sulfones has been developed. Conversion of sulfones to the corresponding sulfinic acid salts is followed by oxidative-amination to give the sulfonamides.
Claims20
A method of preparing sulfonamides comprising the steps of forming a sulfinic acid salt from a sulfone, and treating said sulfinic acid salt with an aminating agent to form the sulfonamide.
A method of preparing sulfonamides of Formula I ##STR14## wherein R.sup.1 is a radical not attached to the sulfur atom through a methylene radical;
- and wherein R.sup.2 and R.sup.3 are independently selected from hydrido, alkyl, alkenyl, aryl and heteroaryl, wherein the aryl and heteroaryl radicals are optionally substituted at a substitutable position with one or more radicals selected from halo, alkyl and alkoxy;
- said method comprising the steps of converting a sulfone into a sulfinic acid salt, and forming the sulfonamide by treating said sulfinic acid salt with an aminating agent.
A method of preparing sulfonamides of Formula II ##STR15## wherein R.sup.1 is a radical not attached to the sulfur atom through a methylene radical,
- said method comprising treating a sulfone of Formula III ##STR16## with a base and an alkylborane in an appropriate solvent to form a trialkylborate-sulfone complex, converting said complex into a sulfinic acid salt, and forming said sulfonamide by treating the sulfinic acid salt with an aminating agent;
- wherein R.sup.4 is selected from hydrido, alkyl, aryl, heteroaryl and alkenyl;
- and wherein any of the foregoing R.sup.1 and R.sup.4 groups may be substituted at one or more substitutable positions with one or more radicals independently selected from halo, alkyl, alkoxy, heteroaryl, aryl and cycloalkenyl.
A method of preparing sulfonamides of Formula II ##STR17## wherein R.sup.1 is a radical not attached to the sulfur atom through a methylene radical,
- said method comprising treating a sulfone of Formula III ##STR18## with a base and an substituted trialkylsilane in an appropriate solvent to form a silylalkylsulfone, treating said silylalkylsulfone with an alkylammonium halide to form a sulfinic acid salt, and forming said sulfonamide by treating the sulfinic acid salt with an aminating agent;
- wherein R.sup.4 is selected from hydrido, alkyl, aryl, heteroaryl and alkenyl;
- and wherein any of the foregoing R.sup.1 and R.sup.4 groups may be substituted at one or more substitutable positions with one or more radicals independently selected from halo, alkyl, alkoxy, heteroaryl, aryl and cycloalkenyl.
Dependencies are inferred from the claim text.