Abstract
Scaffolds of tetrahydrocarbazoles are an important class of biologically active compounds found abundant in nature. In the present investigation, functionalized polycyclic tetrahydrocarbazoles were synthesized using Diels-Alder cycloaddition between fused 5-, 6- and 7-membered ring 2-vinylindoles and various dienophiles. The dienophiles used were N-phenylmaleimides, 1,4-naphthoquinone, and dimethyl acetylenedicarboxylate (DMAD). When 1,4-naphthoquinone was used as a dienophile, the 5-membered ring Diels-Alder adduct was obtained in the oxidized form, but this form was not observed in the case of 6- and 7-membered ring Diels-Alder adducts. The desired product yields ranged from 60–70% and the structure of final compounds were determined using 1D and 2D NMR analysis. 1H NMR studies confirmed excellent diastereoselectivity (>99% de).
Original language | English (US) |
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Pages (from-to) | 6341-6346 |
Number of pages | 6 |
Journal | Tetrahedron |
Volume | 73 |
Issue number | 44 |
DOIs | |
State | Published - Nov 2 2017 |
Bibliographical note
Publisher Copyright:© 2017
Keywords
- 2-Vinylindoles
- Diels-Alder
- Tetrahydrocarbazoles