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Diversity-oriented synthesis of imidazo[2,1-a]isoquinolines.
- Source :
- Chemical Communications; 9/18/2018, Vol. 54 Issue 73, p10240-10243, 4p
- Publication Year :
- 2018
-
Abstract
- Herein, we report an efficient and practical strategy for the synthesis of five types of imidazo[2,1-a]isoquinolines via Cp*Rh<superscript>III</superscript>-catalyzed [4+2] annulation of 2-arylimidazoles and α-diazoketoesters, whose structural and substituted diversity at 5- or 6-position can be precisely controlled by the α-diazoketoester coupling partners. Compared with previous reports, in this study, we merged two attractive C–C cleavage strategies (retro-Claisen and decarboxylation) into the classical C–H functionalization/condensation process by choosing appropriate ester groups (–COOEt, –COOtBu or –COOiPr) or inexpensive additives (HOAc or KOAc). Moreover, the synthetic efficacies of these methods were demonstrated by the concise synthesis of several bioactive compounds and the late-stage modification of representative drugs. [ABSTRACT FROM AUTHOR]
- Subjects :
- ISOQUINOLINE synthesis
SCISSION (Chemistry)
CARBON-hydrogen bonds
Subjects
Details
- Language :
- English
- ISSN :
- 13597345
- Volume :
- 54
- Issue :
- 73
- Database :
- Complementary Index
- Journal :
- Chemical Communications
- Publication Type :
- Academic Journal
- Accession number :
- 131717736
- Full Text :
- https://doi.org/10.1039/c8cc05390a