A Simple, Effective, Green Method for the Regioselective 3-Acylation of Unprotected IndolesReportar como inadecuado




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1

Department of Organic Chemistry, Faculty of Chemistry, University of Science, Vietnam National University, Ho Chi Minh City 70000, Vietnam

2

Department of Science, Systems and Models, Roskilde University, POB 260, Roskilde DK-4000, Denmark





*

Author to whom correspondence should be addressed.



Academic Editor: Jason P. Hallett

Abstract A fast and green method is developed for regioselective acylation of indoles in the 3-position without the need for protection of the NH position. The method is based on Friedel-Crafts acylation using acid anhydrides. The method has been optimized, and YOTf3 in catalytic amounts is found to be the best catalyst together with the commercially available ionic liquid BMIBF4 1-butyl-3-methylimidazolium tetrafluoro-borate as solvent. The reaction is completed in a very short time using monomode microwave irradiation. The catalyst can be reused up to four times without significant loss of activity. A range of substituted indoles are investigated as substrates, and thirteen new compounds have been synthesized. View Full-Text

Keywords: Friedel-Crafts acylation; indole derivatives; ionic liquids; metal triflate; microwave irradiation Friedel-Crafts acylation; indole derivatives; ionic liquids; metal triflate; microwave irradiation





Autor: Phuong Hoang Tran 1, Hai Ngoc Tran 1, Poul Erik Hansen 2,* , Mai Hoang Ngoc Do 1 and Thach Ngoc Le 1

Fuente: http://mdpi.com/



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