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Synfacts 2011(2): 0132-0132
DOI: 10.1055/s-0030-1259386
DOI: 10.1055/s-0030-1259386
Synthesis of Heterocycles
© Georg Thieme Verlag
Stuttgart ˙ New York
Acid-Catalyzed Rearrangement of Ureido-dihydrofurans to N-Pyrrole Ureas
N. N. Kurochkin, A. A. Fesenko, D. A. Cheshkov, M. M. Davudi, A. D. Shutalev*
Moscow State Academy of Fine Chemical Technology and State Scientific Research Institute of Chemistry and Technology of Organoelement Compounds, Moscow, Russian Federation
Further Information
Publication History
Publication Date:
19 January 2011 (online)
Significance
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.