4.5 Article

Direct Assembly of Benzo[e]indoles by Diels-Alder Reaction of Arynes and 2-Vinylpyrroles

Journal

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2016, Issue 17, Pages 2929-2932

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201600334

Keywords

Cycloaddition; Fused-ring systems; Nitrogen heterocycles; Arynes; Protecting groups

Funding

  1. National Natural Science Foundation of China (NSFC) [21102043]
  2. Fundamental Research Funds for the Central Universities

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A direct synthetic strategy for the construction of benzo[e]indoles by Diels-Alder reaction of 2-vinylpyrroles and arynes was developed. By introducing CHPh2 as the N-protecting group, the arynes selectively reacted with the external vinyl group instead of the pyrrole ring itself. A series of substituted benzo[e]indoles were afforded with high selectivity in good yields.

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