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Journal articles on the topic 'Ene-ynamides'

Author: Grafiati
Published: 23 November 2024

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1

Wakamatsu, Hideaki, Yuichi Yoshimura, Yoshimi Sasaki, Masatoshi Kawahata, and Kentaro Yamaguchi. "Synthesis of Various Heterocycles Having a Dienamide Moiety by Ring-Closing Metathesis of Ene-ynamides." Synthesis 50, no. 17 (May 30, 2018): 3467–86. http://dx.doi.org/10.1055/s-0037-1609857.

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Ring-closing metathesis (RCM) of ynamides, having alkene substituents of various lengths on the side chain, was demonstrated using the second-generation Grubbs catalyst. When the reaction of ene-ynamides was carried out in the presence of 5 mol% of the catalyst, RCM proceeded smoothly to give quinoline or isoquinoline derivatives having a dienamide unit in good yields. Furthermore, RCM of ene-ynamides, having one more carbon on the side chain, proceeded smoothly to provide seven-membered heterocycles having a dienamide component. Similarly, eight-membered heterocycles, diazocine and benzodiazocine, were also synthesized by RCM of ene-ynamides in good yields.
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2

Couty, Sylvain, Christophe Meyer, and Janine Cossy. "Gold-catalyzed cycloisomerizations of ene-ynamides." Tetrahedron 65, no. 9 (February 2009): 1809–32. http://dx.doi.org/10.1016/j.tet.2008.10.108.

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3

Deng, Yongming, Jason Zhang, Bradley Bankhead, Jonathan P. Markham, and Matthias Zeller. "Photoinduced oxidative cyclopropanation of ene-ynamides: synthesis of 3-aza[n.1.0]bicycles via vinyl radicals." Chemical Communications 57, no. 43 (2021): 5254–57. http://dx.doi.org/10.1039/d1cc02016a.

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4

Marion, Frédéric, Julien Coulomb, Christine Courillon, Louis Fensterbank, and Max Malacria. "Platinum Dichloride-Catalyzed Cycloisomerization of Ene-ynamides." Organic Letters 6, no. 9 (April 2004): 1509–11. http://dx.doi.org/10.1021/ol049530g.

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5

Cossy, J., S. Couty, and C. Meyer. "Cycloisomerizations of Ene-Ynamides Mediated by Gold." Synfacts 2006, no. 12 (December 2006): 1241. http://dx.doi.org/10.1055/s-2006-955636.

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6

Couty, Sylvain, Christophe Meyer, and Janine Cossy. "Diastereoselective Gold-Catalyzed Cycloisomerizations of Ene-Ynamides." Angewandte Chemie 118, no. 40 (October 13, 2006): 6878–82. http://dx.doi.org/10.1002/ange.200602270.

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7

Couty, Sylvain, Christophe Meyer, and Janine Cossy. "Diastereoselective Gold-Catalyzed Cycloisomerizations of Ene-Ynamides." Angewandte Chemie International Edition 45, no. 40 (October 13, 2006): 6726–30. http://dx.doi.org/10.1002/anie.200602270.

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8

Nishimura, Takahiro, Yuka Takiguchi, Yuko Maeda, and Tamio Hayashi. "Rhodium-Catalyzed Asymmetric Cycloisomerization of 1,6-Ene-ynamides." Advanced Synthesis & Catalysis 355, no. 7 (April 30, 2013): 1374–82. http://dx.doi.org/10.1002/adsc.201300148.

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9

Nishimura, Takahiro, Yuka Takiguchi, Yuko Maeda, and Tamio Hayashi. "ChemInform Abstract: Rhodium-Catalyzed Asymmetric Cycloisomerization of 1,6-Ene-ynamides." ChemInform 44, no. 38 (August 30, 2013): no. http://dx.doi.org/10.1002/chin.201338161.

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10

Huang, Jian, Hui Xiong, Richard P. Hsung, C. Rameshkumar, Jason A. Mulder, and Tyler P. Grebe. "The First Successful Base-Promoted Isomerization of Propargyl Amides to Chiral Ynamides. Applications in Ring-Closing Metathesis of Ene−Ynamides and Tandem RCM of Diene−Ynamides." Organic Letters 4, no. 14 (July 2002): 2417–20. http://dx.doi.org/10.1021/ol020097p.

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11

Huang, Jian, Hui Xiong, Richard P. Hsung, C. Rameshkumar, Jason A. Mulder, and Tyler P. Grebe. "ChemInform Abstract: The First Successful Base-Promoted Isomerization of Propargyl Amides to Chiral Ynamides. Applications in Ring-Closing Metathesis of Ene-Ynamides and Tandem RCM of Diene-Ynamides." ChemInform 33, no. 49 (May 18, 2010): no. http://dx.doi.org/10.1002/chin.200249073.

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12

Meyer, Christophe, Sylvain Couty, and Janine Cossy. "Chemoselective Epoxidation of Ene-Ynamides: Intramolecular Cyclopropanation Induced by the Intermediate α-Oxocarbene." Synlett 2007, no. 18 (October 12, 2007): 2819–22. http://dx.doi.org/10.1055/s-2007-990841.

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13

Li, Sifan, Yu Wang, Zibo Wu, Weiliang Shi, Yibo Lei, Paul W. Davies, and Wei Shu. "A Radical-Initiated Fragmentary Rearrangement Cascade of Ene-Ynamides to [1,2]-Annulated Indoles via Site-Selective Cyclization." Organic Letters 23, no. 18 (August 28, 2021): 7209–14. http://dx.doi.org/10.1021/acs.orglett.1c02519.

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14

Marion, Frederic, Julien Coulomb, Christine Courillon, Louis Fensterbank, and Max Malacria. "Platinum Dichloride Catalyzed Cycloisomerization of Ene-ynamides." ChemInform 35, no. 36 (September 7, 2004). http://dx.doi.org/10.1002/chin.200436031.

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15

Couty, Sylvain, Christophe Meyer, and Janine Cossy. "Diastereoselective Gold-Catalyzed Cycloisomerizations of Ene-Ynamides." ChemInform 38, no. 6 (February 6, 2007). http://dx.doi.org/10.1002/chin.200706038.

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16

Couty, Sylvain, Christophe Meyer, and Janine Cossy. "ChemInform Abstract: Gold-Catalyzed Cycloisomerizations of Ene-ynamides." ChemInform 40, no. 27 (July 7, 2009). http://dx.doi.org/10.1002/chin.200927026.

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17

Yamaoka, Yousuke, Nao Takeuchi, Ken‐ichi Yamada, and Kiyosei Takasu. "Efficient Synthesis of Medium‐sized Nitrogen Heterocycles by Brønsted Acid‐Catalyzed Cyclization of Ene‐ynamides." Asian Journal of Organic Chemistry, April 27, 2023. http://dx.doi.org/10.1002/ajoc.202300145.

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18

Hourtoule, Maxime, and Laurence Miesch. "Regio- and Stereoselective Addition to gem-Difluorinated Ene–Ynamides: Access to Stereodefined Fluorinated Dienes." Organic Letters, May 19, 2022. http://dx.doi.org/10.1021/acs.orglett.2c01593.

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19

Zhu, Bo-Han, Cang-Hai Shen, Min-Ling Nie, Fumin Zheng, Chengzhe Huang, Fan Chen, Long Li, Chao Deng, Long-Wu Ye, and Peng-Cheng Qian. "Highly Site-Selective Oxidative Cyclization of Ene-ynamides via Non-Noble-Metal Catalysis: Access to Functionalized Lactams." Organic Letters, September 19, 2022. http://dx.doi.org/10.1021/acs.orglett.2c02871.

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20

Wang, Nan, Hao-Jin Xu, Ting Li, Long-Wu Ye, and Bo Zhou. "Copper-Catalyzed [2 + 2] Cyclization/Ring Expansion of Ene-Ynamides: Construction of Medium- and Large-Sized Rings." Organic Letters, April 28, 2024. http://dx.doi.org/10.1021/acs.orglett.4c01013.

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21

Sahoo, Akhila Kumar, Prasad Rangu, Kanikarapu Suresh, Shubham Dutta, and Srinivas Vangara. "Metal-Free Stereoselective Addition of Propiolic acids to Ynamides: A Concise Synthetic Route to Highly Substituted Ene-Diyne/Dienyne-(E)-N,O-Acetals." New Journal of Chemistry, 2022. http://dx.doi.org/10.1039/d2nj01907h.

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A straight forward and sustainable approach for 1,2-addition of propiolic acids to ynamide has led to bench stable sp2 (E)-enol-enamides of enediynes & dienynes. The reaction is chemo, regio, as...
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