New gas-phase domino processes leading to benzopyranones and benzofurans

R Alan Aitken; Da Chang

doi:10.3987/COM-15-S(T)14

New gas-phase domino processes leading to benzopyranones and benzofurans

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Abstract

A new domino approach to flavones by gas phase pyrolysis of β,γ-dioxophosphonium ylides containing a 2-methoxyphenyl group is frustrated by unexpected and novel decarbonylation of the intermediate flavon-3-yl radical leading to 2-phenylbenzofuran. Alternative approaches based on dioxolane protection of one carbonyl, or selective elimination in β,β'-dioxo or β-oxo-β'-thioxo ylides were not successful, but pyrolysis of a β-oxo-β'-phenylimino ylide did give the required domino reaction leading to a protected benzopyranone in moderate yield.

Original language	English
Pages (from-to)	164-184
Number of pages	21
Journal	Heterocycles
Volume	93
Issue number	1
Early online date	6 Oct 2015
DOIs	https://doi.org/10.3987/COM-15-S(T)14
Publication status	Published - 2016

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10.3987/COM-15-S(T)14

Aitken_2015_Heterocycles_NewGas_VoR
© 2016 The Japan Institute of Heterocyclic Chemistry. This work has been made available online in accordance with the publisher’s policies. This is the final published version of the work, which was originally published at: https://doi.org/10.3987/COM-15-S(T)14
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abstract = "A new domino approach to flavones by gas phase pyrolysis of β,γ-dioxophosphonium ylides containing a 2-methoxyphenyl group is frustrated by unexpected and novel decarbonylation of the intermediate flavon-3-yl radical leading to 2-phenylbenzofuran. Alternative approaches based on dioxolane protection of one carbonyl, or selective elimination in β,β'-dioxo or β-oxo-β'-thioxo ylides were not successful, but pyrolysis of a β-oxo-β'-phenylimino ylide did give the required domino reaction leading to a protected benzopyranone in moderate yield.",

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AB - A new domino approach to flavones by gas phase pyrolysis of β,γ-dioxophosphonium ylides containing a 2-methoxyphenyl group is frustrated by unexpected and novel decarbonylation of the intermediate flavon-3-yl radical leading to 2-phenylbenzofuran. Alternative approaches based on dioxolane protection of one carbonyl, or selective elimination in β,β'-dioxo or β-oxo-β'-thioxo ylides were not successful, but pyrolysis of a β-oxo-β'-phenylimino ylide did give the required domino reaction leading to a protected benzopyranone in moderate yield.

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New gas-phase domino processes leading to benzopyranones and benzofurans

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