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
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, obta...
Saved in:
| Main Authors: | , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Wiley
2016-01-01
|
| Series: | Journal of Chemistry |
| Online Access: | http://dx.doi.org/10.1155/2016/1504682 |
| Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
| _version_ | 1832548921377816576 |
|---|---|
| author | Sébastien Comesse Adam Daïch |
| author_facet | Sébastien Comesse Adam Daïch |
| author_sort | Sébastien Comesse |
| collection | DOAJ |
| description | 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. |
| format | Article |
| id | doaj-art-d039e74be45a41a6acf7bc348b95bbff |
| institution | Kabale University |
| issn | 2090-9063 2090-9071 |
| language | English |
| publishDate | 2016-01-01 |
| publisher | Wiley |
| record_format | Article |
| series | Journal of Chemistry |
| spelling | doaj-art-d039e74be45a41a6acf7bc348b95bbff2025-02-03T06:12:47ZengWileyJournal of Chemistry2090-90632090-90712016-01-01201610.1155/2016/15046821504682An Unprecedented Straightforward Synthesis of Chiral Pyrrolo[3,4-b]quinolone and Pyrrolo[3,2-b]quinolone Backbones Starting from trans-4-Hydroxy-L-prolineSébastien Comesse0Adam Daïch1Laboratoire de Chimie, URCOM, EA 3221, FR CNRS 3038, Normandie Université, Université du Havre, UFR Sciences et Techniques, 25 rue Philippe Lebon, 76058 Le Havre Cedex, FranceLaboratoire de Chimie, URCOM, EA 3221, FR CNRS 3038, Normandie Université, Université du Havre, UFR Sciences et Techniques, 25 rue Philippe Lebon, 76058 Le Havre Cedex, FranceThe 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.http://dx.doi.org/10.1155/2016/1504682 |
| spellingShingle | Sébastien Comesse Adam Daïch 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 |
| title | 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 |
| title_full | 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 |
| title_fullStr | 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 |
| title_full_unstemmed | 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 |
| title_short | 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 |
| title_sort | unprecedented straightforward synthesis of chiral pyrrolo 3 4 b quinolone and pyrrolo 3 2 b quinolone backbones starting from trans 4 hydroxy l proline |
| url | http://dx.doi.org/10.1155/2016/1504682 |
| work_keys_str_mv | AT sebastiencomesse anunprecedentedstraightforwardsynthesisofchiralpyrrolo34bquinoloneandpyrrolo32bquinolonebackbonesstartingfromtrans4hydroxylproline AT adamdaich anunprecedentedstraightforwardsynthesisofchiralpyrrolo34bquinoloneandpyrrolo32bquinolonebackbonesstartingfromtrans4hydroxylproline AT sebastiencomesse unprecedentedstraightforwardsynthesisofchiralpyrrolo34bquinoloneandpyrrolo32bquinolonebackbonesstartingfromtrans4hydroxylproline AT adamdaich unprecedentedstraightforwardsynthesisofchiralpyrrolo34bquinoloneandpyrrolo32bquinolonebackbonesstartingfromtrans4hydroxylproline |