The azepinones 2 and 5 have been synthesized via ring expansion of the dioxopyrrolidine derivative 1 with dimethylacetylene dicarboxylate or methyl propiolate, respectively, in basic medium (NaH). Acid hydrolysis of 2 gave furo [3,4-c]azepinetetrone 6 whereas alkaline gave furo[3,4-c]azepinetrione 7. Bromination of 6 with N-bromosuccinimide yielded the derivative 8. Compound 6 was treated with methyl orthoformate to afford the derivative 9, which was condensed with benzylamine to pyrrolo[3,4-c]azepinetrione derivative 10.
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Pukyong Natl Univ, Div Image Sci & Engn, Pusan 608737, South Korea
Inje Univ, Dept Biomed Chem, Gimhae 621749, Gyeongnam, South KoreaPukyong Natl Univ, Div Image Sci & Engn, Pusan 608737, South Korea
Parthiban, Paramasivam
Pallela, Ramjee
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Pukyong Natl Univ, Marine Bioproc Res Ctr, Pusan 608737, South KoreaPukyong Natl Univ, Div Image Sci & Engn, Pusan 608737, South Korea
Pallela, Ramjee
Kim, Se-Kwon
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Pukyong Natl Univ, Marine Bioproc Res Ctr, Pusan 608737, South KoreaPukyong Natl Univ, Div Image Sci & Engn, Pusan 608737, South Korea
Kim, Se-Kwon
Park, Dong Ho
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Inje Univ, Dept Biomed Chem, Gimhae 621749, Gyeongnam, South KoreaPukyong Natl Univ, Div Image Sci & Engn, Pusan 608737, South Korea