Synthesis of Novel Isoxazolyl 1,6-Dithia-4,9-diazaspiro[4,4]nonane-3,8-diones and 1-Oxa-6-thia-2,4,9-triazaspiro[4,4]non-2-ene-8-ones

Abstract

The key intermediates, 3-(5-methyl-3-isoxazolyl)-2-arylimino-1,3-thiazolan-4-ones (3), were obtained from 3-amino-5-methylisoxazole (1) by reaction with chloroacetyl chloride followed by treatment with aryl isothiocyanates. Cyclocondensation of 3 with mercapto acetic acid furnished novel isoxazolyl 1,6-dithia-4,9-diazaspiro[4,4]nonane-3,8-diones (4). Cycloaddition of 3 with benzonitrile oxides afforded novel isoxazolyl 1-oxa-6-thia-2,4,9-triazaspiro[4,4]non-2-ene-8-ones (5).

Keywords:

• Cycloaddition
• cyclocondensation
• isoxazolyl spiro thiazolidinones

Notes

∗Compounds 3a–e were recrystallized from aqueous methanol.

∗Compounds 4a–e were recrystallized from aqueous methanol.

∗Compounds 5a–f were recrystallized from benzene.