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A new approach to 3-hydroxyquinoline-2-carboxylic acid |
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| Authors: | Estela Riego,Nuria Bayó ,Carmen Cuevas,Mercedes Á lvarez |
| Affiliation: | a Barcelona Biomedical Research Institute, Barcelona Scientific Park, University of Barcelona, Josep Samitier 1-5, 08028 Barcelona, Spain b Department of Organic Chemistry, University of Barcelona, 08028 Barcelona, Spain c PharmaMar, Avda de los Reyes 1, 28770 Colmenar Viejo, Madrid, Spain d Laboratory of Organic Chemistry, Faculty of Pharmacy, University of Barcelona, 08028 Barcelona, Spain |
| Abstract: | Quinoline-2-carboxylic acid derivatives cap the N-terminal of several natural cyclic peptides with antitumoral activity. A new and convenient route for the preparation of 3-hydroxyquinoline-2-carboxylic acid is discussed. The preparation of the title compound is accomplished by a four-step procedure from 3-hydroxyquinoline via MOM protection of the hydroxyl group, followed by a 1,2-addition of methyllithium to the quinoline ring with concomitant oxidation, and, finally, a two-step oxidation procedure for the transformation of the methyl group to the carboxylic acid along with removal of the MOM group. Furthermore, different attempts to its preparation led to other interesting quinolines, such as 2-chloro-3-hydroxyquinoline-4-carboxylic acid and a protected 3,3′-dihydroxy-2,2′-biquinoline. |
| Keywords: | Heterocycle Biquinoline ortho-Litiation MOM Cyclic peptides |
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