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New Organolithium Addition Methodology to Diversely Functionalized Indoles
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Abstract
A novel synthetic approach to diversely functionalized indoles is described. Boc-protected ortho-aminostyrenes undergo an alkyllithium addition reaction, thereby generating a lithiated intermediate, which upon reaction with specific electrophiles sets up a cascade reaction process between the reacted electrophile and ortho-amino substituent, facilitating an in situ ring closure, followed by dehydration, to generate an indole ring system. This methodology is demonstrated by the synthesis of a range of 3,5-, 1,3,5-, and 2,3,5-substituted indoles.
Citing Articles
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This article has been cited by 18 ACS Journal articles (5 most recent appear below).
Synthesis of Substituted Indoles from 2-Azidoacrylates and ortho-Silyl Aryltriflates
Deng Hong, Zhengbo Chen, Xufeng Lin, and Yanguang WangOrganic Letters2010 12 (20), 4608-4611Synthesis of Substituted Indoles from 2-Azidoacrylates and ortho-Silyl Aryltriflates
Deng Hong, Zhengbo Chen, Xufeng Lin, and Yanguang WangOrganic Letters2010 12 (20), 4608-46112-Azidoacrylates react with benzynes in the presence of PPh3 and CsF to afford substituted indoles in good yields. The reaction involves the formation of iminophosphorane and benzyne and a subsequent double cyclization/hydrolysis/air-oxidation cascade. ...
Lewis Acid Catalyzed Indole Synthesis via Intramolecular Nucleophilic Attack of Phenyldiazoacetates to Iminium Ions
Lei Zhou and Michael P. DoyleThe Journal of Organic Chemistry2009 74 (23), 9222-9224Lewis Acid Catalyzed Indole Synthesis via Intramolecular Nucleophilic Attack of Phenyldiazoacetates to Iminium Ions
Lei Zhou and Michael P. DoyleThe Journal of Organic Chemistry2009 74 (23), 9222-9224Lewis acids catalyze the cyclization of methyl phenyldiazoacetates with an ortho-imino group, prepared from o-aminophenylacetic acid, to give 2,3-substituted indoles in quantitative yields.
Carbolithiation of Conjugated Enynes with Aryllithiums in Microflow System and Applications to Synthesis of Allenylsilanes
Yutaka Tomida, Aiichiro Nagaki and Jun-ichi YoshidaOrganic Letters2009 11 (16), 3614-3617Carbolithiation of Conjugated Enynes with Aryllithiums in Microflow System and Applications to Synthesis of Allenylsilanes
Yutaka Tomida, Aiichiro Nagaki and Jun-ichi YoshidaOrganic Letters2009 11 (16), 3614-3617Carbolithiation of conjugated enynes with aryllithiums generated by Br−Li exchange reaction followed by reaction of the allenyllithium compounds with chlorosilanes was carried out in a microflow system to obtain various allenylsilanes in good yields.
Synthesis of Indoles via Domino Reaction of N-Aryl Amides and Ethyl Diazoacetate
Sun-Liang Cui, Jing Wang and Yan-Guang WangJournal of the American Chemical Society2008 130 (41), 13526-13527Synthesis of Indoles via Domino Reaction of N-Aryl Amides and Ethyl Diazoacetate
Sun-Liang Cui, Jing Wang and Yan-Guang WangJournal of the American Chemical Society2008 130 (41), 13526-13527A general and concise synthesis of functionalized indoles via domino reaction of N-aryl amides and ethyl diazoacetate has been developed. The methodology offers a great potential for the synthesis of biologically active and naturally occurring indole ...
Applications of Enantioselective Carbolithiation of Ortho-Substituted β-Methylstyrenes
Anne-Marie L. Hogan, Thomas Tricotet, Alastair Meek, Shaista S. Khokhar and Donal F. O’SheaThe Journal of Organic Chemistry2008 73 (15), 6041-6044Applications of Enantioselective Carbolithiation of Ortho-Substituted β-Methylstyrenes
Anne-Marie L. Hogan, Thomas Tricotet, Alastair Meek, Shaista S. Khokhar and Donal F. O’SheaThe Journal of Organic Chemistry2008 73 (15), 6041-6044The enantioselective carbolithiation of ortho-substituted (E)-β-methylstyrenes provides access to chiral lithiated intermediates with broad synthetic potential. Specifically, β-methylstyrenes with o-aminomethyl, ether, and oxazoline groups have been ...
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History
- Published In Issue April 09, 2003
- Received January 22, 2003
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