A nickel(0) catalyzed cycloaddition of alkynes and isocyanates that affords pyrimidine-diones |
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Authors: | Hung A. Duong |
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Affiliation: | Department of Chemistry, University of Utah, 315 South 1400 East, Salt Lake City, UT 84112-0850, USA |
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Abstract: | A Ni/N-heterocyclic carbene catalyzed cycloaddition of one alkyne and two isocyanates that affords pyrimidine-dione is described. The key to the success of this protocol is the use of unsymmetrically substituted alkynes that favors the formation of pyrimidine-diones over pyridones. A variety of pyrimidine-diones were prepared. A one-pot cycloaddition and Stille coupling were reported for tributyl(1-propynyl)tin. Competition studies also provide insights into the mechanism of the cycloaddition. |
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