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

DOI

10.3906/kim-1511-66

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

First Page

830

Last Page

840

Recommended Citation

TAN, AYŞE; KOÇ, BİRGÜL; KİSHALI, NURHAN; ŞAHİN, ERTAN; and KARA, YUNUS (2016) "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," Turkish Journal of Chemistry: Vol. 40: No. 5, Article 12. https://doi.org/10.3906/kim-1511-66
Available at: https://journals.tubitak.gov.tr/chem/vol40/iss5/12