Green synthesis of new chiral 1-(arylamino)imidazo[2,1-a]isoindole-2,5-diones from the corresponding α-amino acid arylhydrazides in aqueous medium

New chiral 1-(arylamino)imidazo[2,1-a]isoindole-2,5-dione derivatives were obtained in good to excellent yields via the cyclocondensation of 2-formylbenzoic acid and various α-amino acid arylhydrazides using water as the solvent in the presence of sodium dodecyl sulfate as the surfactant and under s...

Descripción completa

Detalles Bibliográficos
Autores principales: Bouzayani, Nadia, Kraїem, Jamil, Marque, Sylvain, Kacem, Yakdhane, Carlin-Sinclair, Abel, Marrot, Jérôme, Hassine, Béchir Ben
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2018
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6278760/
https://www.ncbi.nlm.nih.gov/pubmed/30546476
http://dx.doi.org/10.3762/bjoc.14.271
_version_ 1783378423585964032
author Bouzayani, Nadia
Kraїem, Jamil
Marque, Sylvain
Kacem, Yakdhane
Carlin-Sinclair, Abel
Marrot, Jérôme
Hassine, Béchir Ben
author_facet Bouzayani, Nadia
Kraїem, Jamil
Marque, Sylvain
Kacem, Yakdhane
Carlin-Sinclair, Abel
Marrot, Jérôme
Hassine, Béchir Ben
author_sort Bouzayani, Nadia
collection PubMed
description New chiral 1-(arylamino)imidazo[2,1-a]isoindole-2,5-dione derivatives were obtained in good to excellent yields via the cyclocondensation of 2-formylbenzoic acid and various α-amino acid arylhydrazides using water as the solvent in the presence of sodium dodecyl sulfate as the surfactant and under simple and minimum manipulation, without purification. The reaction is totally diastereoselective and gives access to the nitrogenated tricyclic core with a relative trans stereochemistry.
format Online
Article
Text
id pubmed-6278760
institution National Center for Biotechnology Information
language English
publishDate 2018
publisher Beilstein-Institut
record_format MEDLINE/PubMed
spelling pubmed-62787602018-12-13 Green synthesis of new chiral 1-(arylamino)imidazo[2,1-a]isoindole-2,5-diones from the corresponding α-amino acid arylhydrazides in aqueous medium Bouzayani, Nadia Kraїem, Jamil Marque, Sylvain Kacem, Yakdhane Carlin-Sinclair, Abel Marrot, Jérôme Hassine, Béchir Ben Beilstein J Org Chem Full Research Paper New chiral 1-(arylamino)imidazo[2,1-a]isoindole-2,5-dione derivatives were obtained in good to excellent yields via the cyclocondensation of 2-formylbenzoic acid and various α-amino acid arylhydrazides using water as the solvent in the presence of sodium dodecyl sulfate as the surfactant and under simple and minimum manipulation, without purification. The reaction is totally diastereoselective and gives access to the nitrogenated tricyclic core with a relative trans stereochemistry. Beilstein-Institut 2018-11-26 /pmc/articles/PMC6278760/ /pubmed/30546476 http://dx.doi.org/10.3762/bjoc.14.271 Text en Copyright © 2018, Bouzayani et al. https://creativecommons.org/licenses/by/4.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0). Please note that the reuse, redistribution and reproduction in particular requires that the authors and source are credited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Bouzayani, Nadia
Kraїem, Jamil
Marque, Sylvain
Kacem, Yakdhane
Carlin-Sinclair, Abel
Marrot, Jérôme
Hassine, Béchir Ben
Green synthesis of new chiral 1-(arylamino)imidazo[2,1-a]isoindole-2,5-diones from the corresponding α-amino acid arylhydrazides in aqueous medium
title Green synthesis of new chiral 1-(arylamino)imidazo[2,1-a]isoindole-2,5-diones from the corresponding α-amino acid arylhydrazides in aqueous medium
title_full Green synthesis of new chiral 1-(arylamino)imidazo[2,1-a]isoindole-2,5-diones from the corresponding α-amino acid arylhydrazides in aqueous medium
title_fullStr Green synthesis of new chiral 1-(arylamino)imidazo[2,1-a]isoindole-2,5-diones from the corresponding α-amino acid arylhydrazides in aqueous medium
title_full_unstemmed Green synthesis of new chiral 1-(arylamino)imidazo[2,1-a]isoindole-2,5-diones from the corresponding α-amino acid arylhydrazides in aqueous medium
title_short Green synthesis of new chiral 1-(arylamino)imidazo[2,1-a]isoindole-2,5-diones from the corresponding α-amino acid arylhydrazides in aqueous medium
title_sort green synthesis of new chiral 1-(arylamino)imidazo[2,1-a]isoindole-2,5-diones from the corresponding α-amino acid arylhydrazides in aqueous medium
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6278760/
https://www.ncbi.nlm.nih.gov/pubmed/30546476
http://dx.doi.org/10.3762/bjoc.14.271
work_keys_str_mv AT bouzayaninadia greensynthesisofnewchiral1arylaminoimidazo21aisoindole25dionesfromthecorrespondingaaminoacidarylhydrazidesinaqueousmedium
AT kraíemjamil greensynthesisofnewchiral1arylaminoimidazo21aisoindole25dionesfromthecorrespondingaaminoacidarylhydrazidesinaqueousmedium
AT marquesylvain greensynthesisofnewchiral1arylaminoimidazo21aisoindole25dionesfromthecorrespondingaaminoacidarylhydrazidesinaqueousmedium
AT kacemyakdhane greensynthesisofnewchiral1arylaminoimidazo21aisoindole25dionesfromthecorrespondingaaminoacidarylhydrazidesinaqueousmedium
AT carlinsinclairabel greensynthesisofnewchiral1arylaminoimidazo21aisoindole25dionesfromthecorrespondingaaminoacidarylhydrazidesinaqueousmedium
AT marrotjerome greensynthesisofnewchiral1arylaminoimidazo21aisoindole25dionesfromthecorrespondingaaminoacidarylhydrazidesinaqueousmedium
AT hassinebechirben greensynthesisofnewchiral1arylaminoimidazo21aisoindole25dionesfromthecorrespondingaaminoacidarylhydrazidesinaqueousmedium

Ejemplares similares