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Paper | Regular issue | Vol 38, No. 8, 1994, pp.1823-1837
Published online, 1st January, 1970
DOI: 10.3987/COM-94-6750
Syntheses of Spiro(oxazolidinediones): Spiro[1H-isoindole-1,5‘-oxazolidine]-2‘,3(2H),4‘-triones and Spiro[1,2-benzisothiazole-3(2H),5‘-oxazolidine]-2‘,4‘-dione 1,1-Dioxides

Jay Wrobel* and Arlene Dietrich

*Wyeth-Ayerst Research Inc., CN 8000, Princeton, NJ 08543-8000, U.S.A.

Abstract

Members of two novel families of spiro(oxazolidinediones) have been prepared. Spiro[1H-isoindole-1,5‘-oxazolidine]-2‘,3(2H),4‘-triones (4) were synthesized from the corresponding 1-hydroxy-1-carboxyethylisoindol-3-one (7) or (10) or their primary amide derivatives (14). In turn 7 and 10 were prepared from 2-bromobenzoic acid amides (6) and (9), or from N-alkylated isoquinolin-1,3,4(2H)-triones (12). Spiro[1,2-benzisothiazole-3(2H),5‘-oxazolidine]-2‘,4‘-dione 1,1-dioxides (5) were constructed from the appropriate 2,3-dihydro-3-hydroxy-1,2-benzisothiazole-3-carboxamide 1,1-dioxide (17). The immediate precursors to 14, ethyl esters (16) and (19), were prepared from benzenesulfonamide (15), or from 2-bromobenzenesulfonamide (18).