A novel class of compounds: synthesis of 5,5 '-carbonyl-bis(5,6-dihydro-4H-furo- and thieno-[2,3-c]pyrrol-4-ones)

Date

2011-11-11

Author

KOZA, GANİ
Balcı, Metin

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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.

Subject Keywords

Acyl azide, Isocyanate, Curtius rearrangement, Urethanes, Furopyrrolone, Thienopyrrolone

URI

https://hdl.handle.net/11511/51302

Journal

TETRAHEDRON

DOI

https://doi.org/10.1016/j.tet.2011.09.050

Collections

Graduate School of Natural and Applied Sciences, Article

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Citation Formats

G. KOZA and M. Balcı, “A novel class of compounds: synthesis of 5,5 ’-carbonyl-bis(5,6-dihydro-4H-furo- and thieno-[2,3-c]pyrrol-4-ones),” TETRAHEDRON, pp. 8679–8684, 2011, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/51302.