Journal
CHEMICAL COMMUNICATIONS
Volume 54, Issue 84, Pages 11897-11900Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c8cc06908e
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Funding
- National Natural Science Foundation of China [21472056, 21602070, 21772051]
- Fundamental Research Funds for the Central Universities [CCNU15ZX002, CCNU16A05002]
- 111 Project [B17019]
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A molecular iodine-mediated formal [2+1+1+1] cycloaddition for the efficient synthesis of pyrrolo[2,1-a]isoquinolines from acetophenones, 1,2,3,4-tetrahydroisoquinoline (THIQ) and DMSO has been developed. Mechanistic studies revealed that DMSO served as the methylene source, and this novel protocol involves intermolecular cycloaddition of two in situ generated intermediates that enable efficient formation of one C-N bond and three C-C bonds via multiple sequential C-H functionalizations.
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