Copper(II)-Catalyzed Synthesis of Benzo[f]pyrido[1,2-a]indole-6,11-dione Derivatives via Naphthoquinone Difunctionalization Reaction

Benzo[f]pyrido[1,2-a]indole-6,11-diones have been synthesized in high yields by copper(II)-catalyzed three-component reactions of acyl bromide, 1,4-naphthoquinone, and pyridine (or isoquinoline) via sp2–C–H difunctionalization of naphthoquinone followed by intramolecular cyclization and oxidative ar...

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Veröffentlicht in:	Journal of organic chemistry 2012-01, Vol.77 (2), p.1191-1197
Hauptverfasser:	Liu, Yun, Sun, Jin-Wei
Format:	Artikel
Sprache:	eng
Schlagworte:	Chemistry Condensed benzenic and aromatic compounds Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with only one n hetero atom and condensed derivatives Kinetics and mechanisms Noncondensed benzenic compounds Organic chemistry Preparations and properties Reactivity and mechanisms
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container_title	Journal of organic chemistry
container_volume	77
creator	Liu, Yun Sun, Jin-Wei
description	Benzo[f]pyrido[1,2-a]indole-6,11-diones have been synthesized in high yields by copper(II)-catalyzed three-component reactions of acyl bromide, 1,4-naphthoquinone, and pyridine (or isoquinoline) via sp2–C–H difunctionalization of naphthoquinone followed by intramolecular cyclization and oxidative aromatization. In an attempt to expand the reaction scope and to help clarify the reaction mechanism, 1,3-dicarbonyl compounds are used in place of acyl bromides to take part in this reaction, and the benzo[f]pyrido[1,2-a]indole-6,11-diones derivatives are also obtained in excellent yields.
doi_str_mv	10.1021/jo2023312
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Org. Chem</addtitle><date>2012-01-20</date><risdate>2012</risdate><volume>77</volume><issue>2</issue><spage>1191</spage><epage>1197</epage><pages>1191-1197</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>Benzo[f]pyrido[1,2-a]indole-6,11-diones have been synthesized in high yields by copper(II)-catalyzed three-component reactions of acyl bromide, 1,4-naphthoquinone, and pyridine (or isoquinoline) via sp2–C–H difunctionalization of naphthoquinone followed by intramolecular cyclization and oxidative aromatization. In an attempt to expand the reaction scope and to help clarify the reaction mechanism, 1,3-dicarbonyl compounds are used in place of acyl bromides to take part in this reaction, and the benzo[f]pyrido[1,2-a]indole-6,11-diones derivatives are also obtained in excellent yields.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>22185652</pmid><doi>10.1021/jo2023312</doi><tpages>7</tpages></addata></record>
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subjects	Chemistry Condensed benzenic and aromatic compounds Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with only one n hetero atom and condensed derivatives Kinetics and mechanisms Noncondensed benzenic compounds Organic chemistry Preparations and properties Reactivity and mechanisms
title	Copper(II)-Catalyzed Synthesis of Benzo[f]pyrido[1,2-a]indole-6,11-dione Derivatives via Naphthoquinone Difunctionalization Reaction
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