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Orthogonal Synthesis of Indolines and Isoquinolines via Aryne Annulation
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Abstract
Described in this report is the development of two unique methodologies exploiting the reactivity of arynes. Reaction of N-carbamoyl-functionalized enamine derivatives with benzyne affords substituted indolines. An orthogonal reactivity is uncovered when related enamine derivatives are modified as amides, such that isoquinolines are formed as the product of condensation with benzyne. This latter transformation is applied to a concise total synthesis of the opiate alkaloid papaverine.
Citing Articles
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This article has been cited by 21 ACS Journal articles (5 most recent appear below).
Synthesis of 2H-Indazoles by the [3 + 2] Dipolar Cycloaddition of Sydnones with Arynes
Yuesi Fang, Chunrui Wu, Richard C. Larock, and Feng ShiThe Journal of Organic Chemistry2011 76 (21), 8840-8851Synthesis of 2H-Indazoles by the [3 + 2] Dipolar Cycloaddition of Sydnones with Arynes
Yuesi Fang, Chunrui Wu, Richard C. Larock, and Feng ShiThe Journal of Organic Chemistry2011 76 (21), 8840-8851A rapid and efficient synthesis of 2H-indazoles has been developed using a [3 + 2] dipolar cycloaddition of sydnones and arynes. A series of 2H-indazoles have been prepared in good to excellent yields using this protocol, and subsequent Pd-catalyzed ...
Synthesis of o-(Dimethylamino)aryl Ketones and Acridones by the Reaction of 1,1-Dialkylhydrazones and Arynes
Anton V. Dubrovskiy and Richard C. LarockOrganic Letters2011 13 (15), 4136-4139Synthesis of o-(Dimethylamino)aryl Ketones and Acridones by the Reaction of 1,1-Dialkylhydrazones and Arynes
Anton V. Dubrovskiy and Richard C. LarockOrganic Letters2011 13 (15), 4136-4139A novel, efficient route to biologically and pharmaceutically important o-(dimethylamino)aryl ketones and acridones has been developed starting from readily available 1,1-dimethylhydrazones of aldehydes and o-(trimethylsilyl)aryl triflates. The reaction ...
A Domino Process for Benzyne Preparation: Dual Activation of o-(Trimethylsilyl)phenols by Nonafluorobutanesulfonyl Fluoride
Takashi Ikawa, Tsuyoshi Nishiyama, Toshifumi Nosaki, Akira Takagi, and Shuji AkaiOrganic Letters2011 13 (7), 1730-1733A Domino Process for Benzyne Preparation: Dual Activation of o-(Trimethylsilyl)phenols by Nonafluorobutanesulfonyl Fluoride
Takashi Ikawa, Tsuyoshi Nishiyama, Toshifumi Nosaki, Akira Takagi, and Shuji AkaiOrganic Letters2011 13 (7), 1730-1733Benzynes were generated from o-(trimethylsilyl)phenols using nonafluorobutanesulfonyl fluoride (NfF) by a domino process, i.e., the nonaflation of the phenolic hydroxyl group of o-(trimethylsilyl)phenols by NfF followed by the attack of the produced ...
Synthesis of Dihydrobenzisoxazoles by the [3 + 2] Cycloaddition of Arynes and Oxaziridines
Arif Kivrak and Richard C. LarockThe Journal of Organic Chemistry2010 75 (21), 7381-7387Synthesis of Dihydrobenzisoxazoles by the [3 + 2] Cycloaddition of Arynes and Oxaziridines
Arif Kivrak and Richard C. LarockThe Journal of Organic Chemistry2010 75 (21), 7381-7387Dihydrobenzisoxazoles are readily prepared in good yields by the [3 + 2] cycloaddition of oxaziridines and arynes. The reaction involves an unusual cleavage of the C−O bond of the oxaziridine and tolerates a variety of substituents on the oxaziridine and ...
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. ...
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History
- Published In Issue February 06, 2008
- Received October 21, 2007
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