The three-component annulation reactions of C, alkyl isocyanide, and dimethyl acetylenedicarboxylate (DMAD) or unsymmetric alkynes are investigated to afford cyclopent-2-en-1-imino- and ketenimine methano-[60]fullerene derivatives, which, upon hydration in the presence of acid, yield the corresponding fullerene amides. Dimethyl 2,3-pentadienedioate, the allene counterpart of DMAD, and ethyl buta-2,3-dienoate undergo four-component annulation with C, alkyl isocyanide, and water under similar conditions to yield cyclopentano-[60]fullerene derivatives with similar amide groups.
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Isocyanide-Induced Annulation Leading to Cyclopento-, Methano-, and Cyclopentano-[60]Fullerene Derivatives.
Org Lett
November 2021
Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey, 123 Bevier Road, Piscataway, New Jersey 08854, United States.
The three-component annulation reactions of C, alkyl isocyanide, and dimethyl acetylenedicarboxylate (DMAD) or unsymmetric alkynes are investigated to afford cyclopent-2-en-1-imino- and ketenimine methano-[60]fullerene derivatives, which, upon hydration in the presence of acid, yield the corresponding fullerene amides. Dimethyl 2,3-pentadienedioate, the allene counterpart of DMAD, and ethyl buta-2,3-dienoate undergo four-component annulation with C, alkyl isocyanide, and water under similar conditions to yield cyclopentano-[60]fullerene derivatives with similar amide groups.
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