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First synthesis of acylated nitrocyclopropanes.


ABSTRACT: Although nitrocyclopropanedicarboxylic acid esters are widely used in organic syntheses, nitrocyclopropanes with an acyl group have not yet been synthesized. When adducts of β-nitrostyrene and 1,3-dicarbonyl compounds are treated with (diacetoxyiodo)benzene and tetrabutylammonium iodide, iodination occurs at the α-position of the nitro group, and the subsequent O-attack of the enol moiety leads to 2,3-dihydrofuran. Cyclopropane was successfully synthesized through C-attack as the acyl group became bulkier. The obtained nitrocyclopropane was transformed into furan upon treatment with tin(II) chloride via a ring-opening/ring-closure process.

SUBMITTER: Iwai K 

PROVIDER: S-EPMC10291240 | biostudies-literature | 2023

REPOSITORIES: biostudies-literature

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First synthesis of acylated nitrocyclopropanes.

Iwai Kento K   Kamidate Rikiya R   Wada Khimiya K   Asahara Haruyasu H   Nishiwaki Nagatoshi N  

Beilstein journal of organic chemistry 20230621


Although nitrocyclopropanedicarboxylic acid esters are widely used in organic syntheses, nitrocyclopropanes with an acyl group have not yet been synthesized. When adducts of β-nitrostyrene and 1,3-dicarbonyl compounds are treated with (diacetoxyiodo)benzene and tetrabutylammonium iodide, iodination occurs at the α-position of the nitro group, and the subsequent <i>O</i>-attack of the enol moiety leads to 2,3-dihydrofuran. Cyclopropane was successfully synthesized through <i>C</i>-attack as the a  ...[more]

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