Synthesis of new hexahydro-1H-isoindole-1,3(2H)-dione derivatives from 2-ethyl/phenyl-3a,4,7,7a-tetrahydro-1H-isoindole-1,3-(2H)-dione

Authors: AYŞE TAN, BİRGÜL KOÇ, NURHAN KİSHALI, ERTAN ŞAHİN, YUNUS KARA

Abstract: A new and appropriate synthesis for hexahydro-1H-isoindole-1,3(2H)-dione derivatives has been developed starting from 3-sulfolene. The epoxidation of 2-ethyl/phenyl-3a,4,7,7a-tetrahydro-1H-isoindole-1,3-(2H)-dione and then the opening of the epoxide with nucleophiles gave hexahydro-1H-isoindole-1,3(2H)-dione derivatives. Amino and triazole derivatives of hexahydro-1H-isoindole-1,3(2H)-dione were synthesized from the formed product by the opening reaction of the epoxide with sodium azide. Hydroxyl analogues were obtained from cis-hydroxylation of 2-ethyl/phenyl-3a,4,7,7a-tetrahydro-1H-isoindole-1,3-(2H)-dione. The hydroxyl groups were converted to acetate.

Keywords: Norcantharimide, cis-hydroxylation, epoxidation, ring opening epoxide, reduction of azide

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