Regio-Controlled Nucleophilic Attack of 3-Thiaisatoic Anhydride by α-Amino Acids: One-Pot Synthesis of 3-(2-Thienyl)imidazolidine-2,4-dione and 3,4-Substituted Thieno[2,3-e][1,4]diazepine-2,5-dione Analogues

Abstract

Convenient syntheses of optically pure 3-(2-thienyl)imidazolidine-2,4-dione (35-63% yields) and 3,4-dihydro-1H-thieno[2,3-e][1,4]diazepine-2,5-dione (35-81% yields) analogues are described. The regioselective ring opening of 1H-thieno[2,3-d][1,3]oxazine-2,4-dione (3-thiaisatoic anhydride), using inexpensive natural and synthetic α-amino acids under aqueous conditions, has been investigated to afford two libraries in a one-pot process.

Key words

thiaisatoic anhydride - 3-(2-thienyl)imidazolidine-2,4-dione - thieno[2,3-e][1,4]diazepine-2,5-dione - diazepine - oxazinedione

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For example, in the case of the aminoisobutyric acid (AIB) residue, the non-decarboxylated analogue 9c was isolated in a large enough amount to allow for characterization by ^¹H and ^¹³C NMR spectroscopy. For more experimental data, refer to the experimental section.