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Abstract
The synthesis and reactivity of β-halo-α-tosyl-substituted alkyl ureas (2, 3) with 1,3-dicarbonyls is reported. The expected Biginelli-type products were not observed; instead, 4,5-dihydrofuran products (4, 5) were isolated in good yields. In the case of 2, a mixture of regioisomers was observed (5, 6) and the 5-ureido-dihydrofuran 5 was isolated cleanly by recrystallization. The utility of these compounds in pyrrole synthesis was demonstrated by their acid-catalyzed rearrangement to afford the 2,3,4-substituted N-pyrrole ureas 7 in good yield.
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