Experimental and theoretical investigation of the coarctate cyclization of (2-Ethynylphenyl)phenyldiazenes |
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Authors: | Shirtcliff Laura D Weakley Timothy J R Haley Michael M Köhler Felix Herges Rainer |
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Institution: | Department of Chemistry, University of Oregon, Eugene, Oregon 97403-1253, USA. |
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Abstract: | A new route to substituted 2-phenyl-2H-indazoles through the cyclization of (2-ethynylphenyl)phenyldiazenes is presented. A coarctate reaction pathway forms the isoindazole carbene under neutral conditions, at moderate temperatures, and without the requirement of a carbene stabilizer. A wide variety of previously unknown diazene precursors was synthesized and cyclized. Trapping of the carbene with a silyl alcohol followed by deprotection affords the 3-hydroxymethyl-2-phenyl-2H-indazoles in good overall yield. The free carbene could also be trapped as a 2 + 1] cycloadduct with 2,3-dimethyl-2-butene. |
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