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Selective construction of polycyclic cyclohepta[b]indoles and cyclopenta[b]indoles via cycloaddition reaction of 3-(indol-3-yl)maleimides and (indol-2-yl)methanols.
- Source :
-
New Journal of Chemistry . 4/14/2023, Vol. 47 Issue 14, p6694-6699. 6p. - Publication Year :
- 2023
-
Abstract
- p-TsOH promoted annulation reaction of 3-(indol-3-yl)maleimides and (indol-2-yl)diphenylmethanols in chloroform afforded functionalized pyrrolo[3′,4′:6,7]cyclohepta[1,2-b:4,5-b′]diindoles in satisfactory yields, in which a formal [4+3] cycloaddition and an unprecedented rearrangement of the maleimide motif from the C3- to C2-position of the indole ring was firstly observed. Alternatively, the similar reaction of 3-(indol-3-yl)maleimides and 3-hydroxy-3-(indol-3-yl)-indolin-2-ones in acetonitrile gave functionalized spiro[indoline-3,9′-pyrrolo[3′,4′:4,5]cyclopenta[1,2-b]indole] in good yields and with high diastereoselectivity. On the other hand, p-TsOH promoted reaction of 3-(indol-3-yl)maleimides and 2-hydroxy-2-(indol-3-yl)-indene-1,3-diones gave functionalized spiro[indene-2,9′-pyrrolo[3′,4′:4,5]cyclopenta[1,2-b]indoles] as major products and spiro[indene-2,9′-pyrrolo[3′,4′:6,7]cyclohepta[1,2-b:4,5-b′]diindoles] as minor products. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 11440546
- Volume :
- 47
- Issue :
- 14
- Database :
- Academic Search Index
- Journal :
- New Journal of Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 162899376
- Full Text :
- https://doi.org/10.1039/d3nj00013c