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Regiospecific C-Acylation of Pyrroles and Indoles Using N-Acylbenzotriazoles
- Source :
- The Journal of Organic Chemistry. 68:5720-5723
- Publication Year :
- 2003
- Publisher :
- American Chemical Society (ACS), 2003.
-
Abstract
- Reactions of pyrrole (2) or 1-methylpyrrole (4) with readily available N-acylbenzotriazoles 1a-g (RCOBt, where R = 4-tolyl, 4-nitrophenyl, 4-diethylaminophenyl, 2-furyl, 2-pyridyl, 2-indolyl, or 2-pyrrolyl) in the presence of TiCl(4) produced 2-acylpyrroles 3a-g and 5a-g in good to excellent yields. 1-Triisopropylsilylpyrrole (6) under the same conditions gave the respective 3-acylpyrroles 7a-g. Similarly, indole (9) and 1-methylindole (11) gave the corresponding 3-acylated derivatives 10a-g and 12a-g. These results demonstrate that N-acylbenzotriazoles such as 1c,f,g are mild, regioselective, and regiospecific C-acylating agents of particular utility when the corresponding acid chlorides are not readily available.
Details
- ISSN :
- 15206904 and 00223263
- Volume :
- 68
- Database :
- OpenAIRE
- Journal :
- The Journal of Organic Chemistry
- Accession number :
- edsair.doi.dedup.....ca29f681d7798ee21550d0f18e314733