Generation and reactivity of N,N-dimethylaminobenzotriazolylcarbene a new nucleophilic carbene |
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Authors: | Alan R. Katritzky Dai Cheng Peter Leeming Ion Ghiviriga Chris M. Hartshorn Peter J. Steel |
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Abstract: | N,N-Dimethylaminobenzotriazolylcarbene ( 5 ) reacted with phenyl isocyanate in a [1+2+2] cycloaddition and then with nucleophiles to generate various hydantoins 10 in a one-pot procedure. It was also found that this novel carbene reacted with trans-dibenzoylethylene ( 11 ) in a [1+4] cycloaddition, generating 2-dimethylamino-3-benzoyl-5-phenylfuran ( 13 ) and 2-phenyl-3-[benzotriazol-1-yl]-4-benzoylfuran ( 14 ) whose structures were confirmed by 1H-13C long range correlations as well as the structure of furan 14 being confirmed by X-ray crystallography. |
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