Quinoline synthesis: scope and regiochemistry of photocyclisation of substituted benzylidenecyclopentanone O-alkyl and O-acetyloximes.

Quinoline synthesis: scope and regiochemistry of photocyclisation of substituted benzylidenecyclopentanone O-alkyl and O-acetyloximes. Research Abstract Details 

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Quinoline synthesis: scope and regiochemistry of photocyclisation of substituted benzylidenecyclopentanone O-alkyl and O-acetyloximes. Abstract Text:

Mark Austin,Oliver J Egan,Raymond Tully,Albert C Pratt,Mark Austin,Oliver J Egan,Raymond Tully,Albert C Pratt,Mark Austin,Oliver J Egan,Raymond Tully,Albert C Pratt,

Irradiation of substituted 2-benzylidenecyclopentanone O-alkyl and O-acetyloximes in methanol provides a convenient synthesis of alkyl, alkoxy, hydroxy, acetoxy, amino, dimethylamino and benzo substituted annulated quinolines. para-Substituents yield 6-substituted-2,3-dihydro-1H-cyclopenta[b]quinolines with 8-substituted products being obtained from ortho-substituted starting materials. Reactions of meta-substituted precursors are highly regioselective, with alkyl substituents leading to 5-substituted 2,3-dihydro-1H-cyclopenta[b]quinolines and more strongly electron-donating substituents generally resulting in 7-substituted products. 2-Furylmethylene and 2-thienylmethylene analogues yield annulated furo- and thieno-[2,3e]pyridines respectively. Sequential E- to Z-benzylidene group isomerisation and six pi-electron cyclisation steps result in formation of a short-lived dihydroquinoline intermediate which spontaneously aromatises by elimination of an alcohol or acetic acid. For 2-benzylidenecyclopentanone O-allyloxime, singlet excited states are involved in both steps.

Quinoline synthesis: scope and regiochemistry of photocyclisation of substituted benzylidenecyclopentanone O-alkyl and O-acetyloximes. Publishing Authors By Initials

M Austin,OJ Egan,R Tully,AC Pratt,M Austin,OJ Egan,R Tully,AC Pratt,M Austin,OJ Egan,R Tully,AC Pratt,

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Quinoline synthesis: scope and regiochemistry of photocyclisation of substituted benzylidenecyclopentanone O-alkyl and O-acetyloximes. Journal Published:

PUBLICATION TYPE: Journal Article

Journal: Organic & biomolecular chemistry

VOLUME: 5

Page Numbers: 3778-86

Journal Abbreviation: Org. Biomol. Chem.

ISSN: 1477-0520

DAY: 11

MONTH: 10

YEAR: 2007

Quinoline synthesis: scope and regiochemistry of photocyclisation of substituted benzylidenecyclopentanone O-alkyl and O-acetyloximes. Information

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LANGUAGE: eng

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AFFILIATION: School of Chemical Sciences, Dublin City University, Dublin 9, Ireland. albert.pratt@dcu.ie.

Country: England

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MEDLINETA: Org Biomol Chem

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