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A Versatile Cyclodehydration Reaction for the Synthesis of Isoquinoline and β-Carboline Derivatives
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Abstract
The direct conversion of various amides to isoquinoline and β-carboline derivatives via mild electrophilic amide activation, with trifluoromethanesulfonic anhydride in the presence of 2-chloropyridine, is described. Low-temperature amide activation followed by cyclodehydration upon warming provides the desired products with short overall reaction times. The successful use of nonactivated and halogenated phenethylene derived amides, N-vinyl amides, and optically active substrates is noteworthy.
Citing Articles
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This article has been cited by 6 ACS Journal articles (5 most recent appear below).
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Huijun Dong, Regina T. Latka, and Tom G. DriverOrganic Letters2011 Article ASAPA range of γ-carbolines were produced stereoselectively from ruthenium(III)-catalyzed reactions of 3-pyridyl substituted aryl azides. Other catalysts and conditions were neither as selective nor as high-yielding. This method was used to synthesize ...
Synthesis of H-Pyrazolo[5,1-a]isoquinolines via Copper(II)-Catalyzed Oxidation of an Aliphatic C−H Bond of Tertiary Amine in Air
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Shaoyu Li and Jie WuOrganic Letters2011 13 (4), 712-715A multicomponent reaction of 2-alkynylbenzaldehyde, sulfonohydrazide, and tertiary amine is discovered, which generates the unexpected H-pyrazolo[5,1-a]isoquinolines in good yields under mild conditions. In the reaction process, silver(I)-catalyzed ...
Controlled and Chemoselective Reduction of Secondary Amides
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Guillaume Pelletier, William S. Bechara, and André B. CharetteJournal of the American Chemical Society2010 132 (37), 12817-12819This communication describes a metal-free methodology involving an efficient and controlled reduction of secondary amides to imines, aldehydes, and amines in good to excellent yields under ambient pressure and temperature. The process includes a ...
Pd(II)-Catalyzed Synthesis of Carbolines by Iminoannulation of Internal Alkynes via Direct C−H Bond Cleavage Using Dioxygen as Oxidant
Shengtao Ding, Zhuangzhi Shi and Ning JiaoOrganic Letters2010 12 (7), 1540-1543Pd(II)-Catalyzed Synthesis of Carbolines by Iminoannulation of Internal Alkynes via Direct C−H Bond Cleavage Using Dioxygen as Oxidant
Shengtao Ding, Zhuangzhi Shi and Ning JiaoOrganic Letters2010 12 (7), 1540-1543A palladium-catalyzed iminoannulation of internal alkynes via direct C−H bond cleavage was developed. Dioxygen was employed as a clean oxidant in this kind of catalysis. Carbolines were synthesized from tert-butylimines of N-substituted indole-2-...
Synthesis of Structurally Simplified Analogues of Pancratistatin: Truncation of the Cyclitol Ring
Madhuri Manpadi, Artem S. Kireev, Igor V. Magedov, Jeff Altig, Paul Tongwa, Mikhail Yu. Antipin, Antonio Evidente, Willem A. L. van Otterlo and Alexander KornienkoThe Journal of Organic Chemistry2009 74 (18), 7122-7131Synthesis of Structurally Simplified Analogues of Pancratistatin: Truncation of the Cyclitol Ring
Madhuri Manpadi, Artem S. Kireev, Igor V. Magedov, Jeff Altig, Paul Tongwa, Mikhail Yu. Antipin, Antonio Evidente, Willem A. L. van Otterlo and Alexander KornienkoThe Journal of Organic Chemistry2009 74 (18), 7122-7131Pancratistatin is a phenanthridone-type natural product isolated from several plants of the Amaryllidaceae family. Its potent antiproliferative, antivascular, antiviral, and antiparasitic properties have attracted the attention of synthetic, biological, ...
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History
- Published In Issue August 21, 2008
- Article ASAPJuly 19, 2008
- Received: June 04, 2008
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