4H-Furo [3, 4-d][1, 3] oxazine-2 (1H), 4-dione. A furan analog of isatoic anhydride

JB Press, NH Eudy, TO Olagbemiro

Index: Press, Jeffery B.; Eudy, Nancy H.; Olagbemiro, Timothy O. Journal of Organic Chemistry, 1981 , vol. 46, # 19 p. 3853 - 3856

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Citation Number: 4

Abstract

The title compound 2 was prepared in four steps from diethyl 3, 4-furandicarboxylate. Reactions of 2 with nitrogen and oxygen nucleophiles occur exclusively at the nitrogen carbonyl to give ureido acids 6 or carbamato acids 8 under a variety of reaction conditions. The results are in contrast to the reactions of isatoic anhydride 1. In order to achieve substitution at the carbonyl adjacent to the furan ring, carbamato acid 8a waa derivatized ...