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An Unprecedented Straightforward Synthesis of Chiral Pyrrolo[3,4-b]quinolone and Pyrrolo[3,2-b]quinolone Backbones Starting from trans-4-Hydroxy-L-proline
Joint Authors
Source
Issue
Vol. 2016, Issue 2016 (31 Dec. 2016), pp.1-5, 5 p.
Publisher
Hindawi Publishing Corporation
Publication Date
2016-01-18
Country of Publication
Egypt
No. of Pages
5
Main Subjects
Abstract EN
The straightforward synthesis of pyrrolo[3,4-b]quinolone and pyrrolo[3,2-b]quinolone backbones, which can be found in molecules exhibiting anticancer activities, is presented.
The key step of the process is an efficient and unprecedented Friedländer condensation between an oxoproline carbamate, obtained in 3 steps and good yield starting from commercially available and relatively cheap trans-4-hydroxy-L-proline, and various 2-amino-substituted carbonyl derivatives.
It was demonstrated that the formation of the two possible regioisomers was fully triggered by both the R substituent onto the 2-amino-substituted carbonyl compounds and the ester function onto the oxoproline carbamate.
Thus, in some cases, a complete regiocontrol for the Friedländer reaction could be attained.
American Psychological Association (APA)
Comesse, S.& Daïch, Adam. 2016. An Unprecedented Straightforward Synthesis of Chiral Pyrrolo[3,4-b]quinolone and Pyrrolo[3,2-b]quinolone Backbones Starting from trans-4-Hydroxy-L-proline. Journal of Chemistry،Vol. 2016, no. 2016, pp.1-5.
https://search.emarefa.net/detail/BIM-1107541
Modern Language Association (MLA)
Comesse, S.& Daïch, Adam. An Unprecedented Straightforward Synthesis of Chiral Pyrrolo[3,4-b]quinolone and Pyrrolo[3,2-b]quinolone Backbones Starting from trans-4-Hydroxy-L-proline. Journal of Chemistry No. 2016 (2016), pp.1-5.
https://search.emarefa.net/detail/BIM-1107541
American Medical Association (AMA)
Comesse, S.& Daïch, Adam. An Unprecedented Straightforward Synthesis of Chiral Pyrrolo[3,4-b]quinolone and Pyrrolo[3,2-b]quinolone Backbones Starting from trans-4-Hydroxy-L-proline. Journal of Chemistry. 2016. Vol. 2016, no. 2016, pp.1-5.
https://search.emarefa.net/detail/BIM-1107541
Data Type
Journal Articles
Language
English
Notes
Includes bibliographical references
Record ID
BIM-1107541