Journal
TETRAHEDRON
Volume 67, Issue 45, Pages 8679-8684Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2011.09.050
Keywords
Acyl azide; Isocyanate; Curtius rearrangement; Urethanes; Furopyrrolone; Thienopyrrolone
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Funding
- Scientific and Technological Research Council of Turkey (TUBITAK) [110-R-001]
- Department of Chemistry at Middle East Technical University
- Turkish Academy of Sciences (TUBA)
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We hereby report the first synthesis of novel class of compounds, 5,5'-carbonyl-bis(5,6-dihydro-4H-thieno- and furo-[2,3-c]pyrrol-4-one starting from methyl 2-(2-methoxy-2-oxoethyl) thiophene- and furan-3-carboxylate, respectively. The ester functionalities connected to methylene group were regiospecifically converted to the desired monoacyl azides. Curtius rearrangement of acyl azides followed by hydrolysis of the formed isocyanates gave the symmetrical urea derivatives. Cyclization of the ester groups provided the target compounds. (C) 2011 Elsevier Ltd. All rights reserved.
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