Abstract
The "click chemistry" of using organic azides and terminal alkynes is arguably the most efficient and straightforward route to the synthesis of 1,2,3-triazoles. In this paper, an alternative and direct access to ethyl 1-(4-methoxyphenyl)-5-phenyl-1H-1,2,3-triazole-4-carboxylate is described. Treatment of ethyl diazoacetate with 4-methoxyaniline derived aryl imines in the presence of 1,8-diazabicyclo [5.4.0]undec-7-ene provided fully substituted 1,2,3-triazoles in good to high chemical yields. The basemediated reaction tolerates various substituted phenyl imines as well as ethyl diazoacetate or the more bulky diazoacetamide. A reasonable mechanism is proposed that involves the addition of an imine nitrogen atom to the terminal nitrogen atom of the diazo compound, followed by aromatization to give the 1,2,3-triazole. The presence of the 4-carboxy group is advantageous as it can be easily transformed into other functional groups.
Original language | English |
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Pages (from-to) | 328-333 |
Number of pages | 6 |
Journal | Chemistry - An Asian Journal |
Volume | 5 |
Issue number | 2 |
DOIs | |
Publication status | Published - 2010 Feb 1 |
Keywords
- Aromaticity
- Cycloaddition
- Diazo compounds
- Heterocycles
- Triazoles
ASJC Scopus subject areas
- Biochemistry
- Organic Chemistry
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CCDC 732055: Experimental Crystal Structure Determination
Chen, J.-H. (Creator), Liu, S.-R. (Creator) & Chen, K. (Creator), Unknown Publisher, 2010
DOI: 10.5517/ccskrpr, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccskrpr&sid=DataCite
Dataset
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CCDC 732056: Experimental Crystal Structure Determination
Chen, J.-H. (Creator), Liu, S.-R. (Creator) & Chen, K. (Creator), Unknown Publisher, 2010
DOI: 10.5517/ccskrqs, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccskrqs&sid=DataCite
Dataset
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CCDC 732057: Experimental Crystal Structure Determination
Chen, J.-H. (Creator), Liu, S.-R. (Creator) & Chen, K. (Creator), Unknown Publisher, 2010
DOI: 10.5517/ccskrrt, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccskrrt&sid=DataCite
Dataset