First Inverse Electron-Demand Diels–Alder Methodology of 3-Chloroindoles and Methyl Coumalate to Carbazoles.
- Resource Type
- Article
- Authors
- Guney, Tezcan; Lee, Jennifer J.; Kraus, George A.
- Source
- Organic Letters. Feb2014, Vol. 16 Issue 4, p1124-1127. 4p.
- Subject
- *ELECTRONS
*DIELS-Alder reaction
*INDOLE
*CARBAZOLE
*SUBSTITUTION reactions
*METAL catalysts
- Language
- ISSN
- 1523-7060
Thefirst successful inverse electron-demand Diels–Alder has beendemonstrated with the 2-pyrone methyl coumalate in conjunctionwith substituted indoles. Utilizing 1-alkyl-3-chloroindoles as theelectron-rich dienophile efficiently generates carbazoles withoutthe need for additional metal catalysts. Through a thermal, one-potDiels–Alder/decarboxylation/eliminationdomino sequence, access to a class of 3-methylcarbazoles is rapidlygenerated with exclusive regiocontrol in up to 90% yield. [ABSTRACT FROM AUTHOR]