4.4 Article

Synthesis of Indeno[b]indole and Naphtho[a]carbazole Derivatives Involving Diels-Alder Reaction of Isobenzofurans

Journal

CHEMISTRYSELECT
Volume 2, Issue 26, Pages 7899-7903

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/slct.201701851

Keywords

Diels-Alder; Fischer indole synthesis; indeno[b]indole; indeno[b]indolones; Isobenzofuran; naphtho[a]carbazole

Funding

  1. Department of Science and Technology (DST), New Delhi
  2. Council of Scientific and Industrial Research (CSIR), New Delhi

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Diels-Alder reaction of 1,3-diarylisobenzofurans with cyclopenten-1-one as well as 2-cyclohexen-1-one in the presence of TMSOTf in DCM at 0 degrees C furnished 4,5-diarylbenzo[e]inden-1-ones and 6,7-diarylbenzo[f]-tetralones. The benzo[e]inden-1-ones/benzo[f]-tetralones upon Fischer indolization led to the formation of indeno[b]indoles and dihydronaphtho[a]carbazoles, respectively.

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