5-Chromonylidene-hydantoins, 2-Thiohydantoins, Synthesis and Reaction with Some Alkylhalides, Some Amines and Some Diazoalkanes

Abstract

5-Chromonylidene-hydantoin, 2-thiohydantoin derivatives 2a–g, 3a,b were prepared by condensation of 3-formylchromones 1a,b with hydantoin, 2-thiohydantoin derivatives. Compounds 2a,b undergo Mannich reaction with formaldehyde and morpholine to give the corresponding Mannich prouducts 5a,b respectively. Reaction of 2a,b with alkylhalides namely Methyl iodide, Phenacly bromide, and Chloroacetic acid afforded the corresponding compounds 6a,b, 7a,b, 9a,b and 10a,b respectively. Reaction of 5-Chromonylidene-2-methylthio-hydantoin 6a,b with secondry and primary amines such as morpholine, piprazine, anthranilic acid, and glycine afforded the Glycocyamidine derivatives 11a,b, 12a,b, 13a,b and 15a,b. On reacting 2a,b with dazoalkanes afforded 16a,b and 17a,b respectively.

Key Words:

• 2-Thiohydantoin
• alkylthiohydantoin
• chromones
• diazoalkanes
• glycocyamidines
• hydantoin