TY - JOUR
T1 - New gas-phase domino processes leading to benzopyranones and benzofurans
AU - Aitken, R Alan
AU - Chang, Da
PY - 2016
Y1 - 2016
N2 - 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.
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.
UR - https://www.heterocycles.jp/newlibrary/libraries/prepress
UR - https://www.scopus.com/pages/publications/85014448864
U2 - 10.3987/COM-15-S(T)14
DO - 10.3987/COM-15-S(T)14
M3 - Article
SN - 1881-0942
VL - 93
SP - 164
EP - 184
JO - Heterocycles
JF - Heterocycles
IS - 1
ER -