Cart
Article
Multicomponent Reactions of Convertible Isonitriles
Abstract
A new family of unsaturated isonitriles has been prepared by the base-promoted ring-opening of oxazoles, offering an alternative to the conventional formamide dehydration route. These compounds undergo the full complement of multicomponent reactions for which isonitriles are known and offer the desirable trait of giving amide products that readily participate in acyl substitution reactions (hence, they are convertible). Moreover, they do not have the objectionable odors for which isonitriles are typically known, making them more accessible as reagents for organic synthesis. One focus of the work is isonitriles bearing perfluorinated alkyl groups that enable the ready separation of such reagents from nonfluorinated reaction products using the “light” fluorous method of fluorous solid-phase extraction.
1H NMR spectra for 10h, 13, 25−40, 41c, and 43−47. 13C NMR spectra for 10h, 13, 26−38, 40,41c, and 43−46. Experimental procedures for the preparation of 28, 29, 31, 33, 34, 37−40, 41b, 42, and 44−46. This material is available free of charge via the Internet at http://pubs.acs.org.
Citation data is made available by participants in CrossRef's Cited-by Linking service. For a more comprehensive list of citations to this article, users are encouraged to perform a search in SciFinder.
Applications of C–H Functionalization Logic to Cyclobutane Synthesis
Will R. Gutekunstand Phil S. BaranThe Journal of Organic Chemistry2014 79 (6), 2430-2452
Reaction of β-Lactam Carbenes with 2-Pyridyl Isonitriles: A One-Pot Synthesis of 2-Carbonyl-3-(pyridylamino)imidazo[1,2-a]pyridines Useful as Fluorescent Probes for Mercury Ion
Na Shao, Guang-Xian Pang, Cai-Xia Yan, Gao-Feng Shi, and Ying ChengThe Journal of Organic Chemistry2011 76 (18), 7458-7465
Ligand-Free CuO Nanospindle Catalyzed Arylation of Heterocycle C–H Bonds
Wu Zhang, Qinglong Zeng, Xinming Zhang, Yujie Tian, Yun Yue, Yujun Guo, and Zhenghua WangThe Journal of Organic Chemistry2011 76 (11), 4741-4745
Supported p-Toluenesulfonic Acid as a Highly Robust and Eco-Friendly Isocyanide Scavenger
Jhonny Azuaje, Alberto Coelho, Abdelaziz El Maatougui, José Manuel Blanco, and Eddy SoteloACS Combinatorial Science2011 13 (1), 89-95
Comprehensive Survey of Chemical Libraries for Drug Discovery and Chemical Biology: 2009
Roland E. Dolle, Bertrand Le Bourdonnec, Karin Worm, Guillermo A. Morales, Craig J. Thomas, and Wei ZhangJournal of Combinatorial Chemistry2010 12 (6), 765-806![Cover Image]()
Use of Cyclohexylisocyanide and Methyl 2-Isocyanoacetate as Convertible Isocyanides for Microwave-Assisted Fluorous Synthesis of 1,4-Benzodiazepine-2,5-dione Library
Hongyu Zhou, Wei Zhangand Bing YanJournal of Combinatorial Chemistry2010 12 (1), 206-214
