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

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...

Full description

Bibliographic Details
Main Authors: Sébastien Comesse, Adam Daïch
Format: Article
Language:English
Published: Hindawi Limited 2016-01-01
Series:Journal of Chemistry
Online Access:http://dx.doi.org/10.1155/2016/1504682
id doaj-d039e74be45a41a6acf7bc348b95bbff
record_format Article
spelling doaj-d039e74be45a41a6acf7bc348b95bbff2020-11-24T20:46:40ZengHindawi LimitedJournal 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
collection DOAJ
language English
format Article
sources DOAJ
author Sébastien Comesse
Adam Daïch
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
author_facet Sébastien Comesse
Adam Daïch
author_sort Sébastien Comesse
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_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_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_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
publisher Hindawi Limited
series Journal of Chemistry
issn 2090-9063
2090-9071
publishDate 2016-01-01
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.
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
_version_ 1716811900071706624

Similar Items