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Iodocarbocyclization Reaction of β-Ketoesters and Alkynes
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Section:Abstract
Iodocyclopentenes are formed at room temperature upon straight reaction of δ-alkynyl-β-ketoesters with I2 for several hours. Cyclizations involving terminal and substituted (alkyl, aryl, Br, I) alkynes were accessed. Twelve examples with yields ranging from 20% up to 80% are reported (out of them eight cases are above 60%). These results present the first examples of the iodonium-promoted 5-endo-dig carbocyclization of active methyne substrates onto alkynes.
Citing Articles
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This article has been cited by 15 ACS Journal articles (5 most recent appear below).
Iodocyclization of Hydroxylamine Derivatives Based on the Control of Oxidative Aromatization Leading to 2,5-Dihydroisoxazoles and Isoxazoles
Takashi Okitsu, Kana Sato, Taterao M. Potewar, and Akimori WadaThe Journal of Organic Chemistry2011 Article ASAPIodocyclization of Hydroxylamine Derivatives Based on the Control of Oxidative Aromatization Leading to 2,5-Dihydroisoxazoles and Isoxazoles
Takashi Okitsu, Kana Sato, Taterao M. Potewar, and Akimori WadaThe Journal of Organic Chemistry2011 Article ASAPAn efficient method for the synthesis of 2,5-dihydroisoxazoles and isoxazoles using iodocyclization of N-alkoxycarbonyl O-propargylic hydroxylamines has been developed. 2,5-Dihydro-4-iodoisoxazole underwent the cross-coupling reactions without ...
CuI/I2-Promoted Electrophilic Tandem Cyclization of 2-Ethynylbenzaldehydes with ortho-Benzenediamines: Synthesis of Iodoisoquinoline-Fused Benzimidazoles
Huang-Che Ouyang, Ri-Yuan Tang, Ping Zhong, Xing-Guo Zhang, and Jin-Heng LiThe Journal of Organic Chemistry2011 76 (1), 223-228CuI/I2-Promoted Electrophilic Tandem Cyclization of 2-Ethynylbenzaldehydes with ortho-Benzenediamines: Synthesis of Iodoisoquinoline-Fused Benzimidazoles
Huang-Che Ouyang, Ri-Yuan Tang, Ping Zhong, Xing-Guo Zhang, and Jin-Heng LiThe Journal of Organic Chemistry2011 76 (1), 223-228An efficient tandem route to the synthesis of iodoisoquinoline-fused benzimidazole derivatives including an iodocyclization strategy has been developed. In the presence of CuI, a variety of 2-ethynylbenzaldehydes underwent the tandem reaction with ...
Room-Temperature Metal-Free Electrophilic 5-endo-Selective Iodocarbocyclization of 1,5-Enynes
Alexandre Pradal, Alexandre Nasr, Patrick Y. Toullec, and Veronique MicheletOrganic Letters2010 12 (22), 5222-5225Room-Temperature Metal-Free Electrophilic 5-endo-Selective Iodocarbocyclization of 1,5-Enynes
Alexandre Pradal, Alexandre Nasr, Patrick Y. Toullec, and Veronique MicheletOrganic Letters2010 12 (22), 5222-5225A highly efficient NIS-promoted iodocarbocyclization reaction of various functionalized 1,5-enynes is described via a 5-endo diastereoselective process. The cyclizations are conducted in the presence of 1.2 equiv of N-iodosuccinimide in dichloromethane ...
Reagent-Controlled Oxidative Aromatization in Iodocyclization: Switchable Access to Dihydropyrazoles and Pyrazoles
Takashi Okitsu, Kana Sato and Akimori WadaOrganic Letters2010 12 (15), 3506-3509Reagent-Controlled Oxidative Aromatization in Iodocyclization: Switchable Access to Dihydropyrazoles and Pyrazoles
Takashi Okitsu, Kana Sato and Akimori WadaOrganic Letters2010 12 (15), 3506-3509Switchable access to dihydropyrazoles and pyrazoles has been developed from common hydrazides by reagent-controlled iodocyclization. Controlling the oxidative aromatization in iodocyclization for heterocycles is reported for the first time, and this ...
Diversity-Oriented Construction of Highly Substituted Indolizinones
Kyungsun Kim and Ikyon KimJournal of Combinatorial Chemistry2010 12 (3), 379-382Diversity-Oriented Construction of Highly Substituted Indolizinones
Kyungsun Kim and Ikyon KimJournal of Combinatorial Chemistry2010 12 (3), 379-382Rapid generation of a small library of highly functionalized indolizonones was realized by exploiting three palladium-catalyzed cross-coupling reactions of 2-iodoindolizinones which in turn were readily accessed via sequential iodine-mediated cyclization/...
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History
- Published In Issue July 19, 2007
- Received May 4, 2007
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