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Regioselective Synthesis of the 5,6-Dihydro-4H-furo[2,3-c]pyrrol-4-one Skeleton: A New Class of Compounds
Date
2010-01-01
Author
Koza, Gani
Karahan, Emrah
Balcı, Metin
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We hereby report the first preparation of the 5,6-dihydro-4H-furo[2.3-c]pyrrol-4-one (3) and its derivatives starting from methyl 3-(methoxycarbonyl)furnan-2-acetate (8). The ester functionality connected to the methylene group was regiospecifically converted to the desired monohydrazide 9. Conversion of 9 into the acyl azide In followed by Curtius rearrangement gave the corresponding isocyanate derivative 11 (Scheme 2). Reaction of 11 with different nucleophiles produced urethane and urea derivatives (Scheme 3). Intramolecular cyclization reactions provided the target compounds (Scheme 5). Removal of the amine-protecting group formed the title compound 3.
Subject Keywords
Physical and Theoretical Chemistry
,
Inorganic Chemistry
,
Organic Chemistry
,
Biochemistry
,
Drug Discovery
,
Catalysis
URI
https://hdl.handle.net/11511/51662
Journal
HELVETICA CHIMICA ACTA
DOI
https://doi.org/10.1002/hlca.200900448
Collections
Graduate School of Natural and Applied Sciences, Article
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We hereby report the first preparation of the 3,4-dihydrofuro[3,2-d]pyrimidin-2(1H)-one skeleton formed by two controlled Curtius rearrangements of the corresponding acyl azides, prepared from 2-(2-methoxy-2-oxoethyl)furan-3-carboxylate via the hydrazide. Rearrangement of the acyl azides followed by trapping by nucleophiles and intramolecular trapping provided the target compounds.
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G. Koza, E. Karahan, and M. Balcı, “Regioselective Synthesis of the 5,6-Dihydro-4H-furo[2,3-c]pyrrol-4-one Skeleton: A New Class of Compounds,”
HELVETICA CHIMICA ACTA
, pp. 1698–1704, 2010, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/51662.