Stereoselective synthesis of fused tetrahydroquinazolines through one-pot double [3 + 2] dipolar cycloadditions followed by [5 + 1] annulation

The one-pot [3 + 2] cycloaddition of an azomethine ylide with a maleimide followed by another [3 + 2] cycloaddition of an azide with the second maleimide gives a 1,5-diamino intermediate which is used for a sequential aminomethylation reaction with formaldehyde through [5 + 1] annulation to afford a...

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Autores principales: Zhang, Xiaofeng, Pham, Kenny, Liu, Shuai, Legris, Marc, Muthengi, Alex, Jasinski, Jerry P, Zhang, Wei
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2016
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5082442/
https://www.ncbi.nlm.nih.gov/pubmed/27829928
http://dx.doi.org/10.3762/bjoc.12.211
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author Zhang, Xiaofeng
Pham, Kenny
Liu, Shuai
Legris, Marc
Muthengi, Alex
Jasinski, Jerry P
Zhang, Wei
author_facet Zhang, Xiaofeng
Pham, Kenny
Liu, Shuai
Legris, Marc
Muthengi, Alex
Jasinski, Jerry P
Zhang, Wei
author_sort Zhang, Xiaofeng
collection PubMed
description The one-pot [3 + 2] cycloaddition of an azomethine ylide with a maleimide followed by another [3 + 2] cycloaddition of an azide with the second maleimide gives a 1,5-diamino intermediate which is used for a sequential aminomethylation reaction with formaldehyde through [5 + 1] annulation to afford a novel polycyclic scaffold bearing tetrahydroquinazoline, pyrrolidine, pyrrolidinedione, and N-substituted maleimide in stereoselective fashion.
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spelling pubmed-50824422016-11-09 Stereoselective synthesis of fused tetrahydroquinazolines through one-pot double [3 + 2] dipolar cycloadditions followed by [5 + 1] annulation Zhang, Xiaofeng Pham, Kenny Liu, Shuai Legris, Marc Muthengi, Alex Jasinski, Jerry P Zhang, Wei Beilstein J Org Chem Full Research Paper The one-pot [3 + 2] cycloaddition of an azomethine ylide with a maleimide followed by another [3 + 2] cycloaddition of an azide with the second maleimide gives a 1,5-diamino intermediate which is used for a sequential aminomethylation reaction with formaldehyde through [5 + 1] annulation to afford a novel polycyclic scaffold bearing tetrahydroquinazoline, pyrrolidine, pyrrolidinedione, and N-substituted maleimide in stereoselective fashion. Beilstein-Institut 2016-10-18 /pmc/articles/PMC5082442/ /pubmed/27829928 http://dx.doi.org/10.3762/bjoc.12.211 Text en Copyright © 2016, Zhang 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), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. 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
Zhang, Xiaofeng
Pham, Kenny
Liu, Shuai
Legris, Marc
Muthengi, Alex
Jasinski, Jerry P
Zhang, Wei
Stereoselective synthesis of fused tetrahydroquinazolines through one-pot double [3 + 2] dipolar cycloadditions followed by [5 + 1] annulation
title Stereoselective synthesis of fused tetrahydroquinazolines through one-pot double [3 + 2] dipolar cycloadditions followed by [5 + 1] annulation
title_full Stereoselective synthesis of fused tetrahydroquinazolines through one-pot double [3 + 2] dipolar cycloadditions followed by [5 + 1] annulation
title_fullStr Stereoselective synthesis of fused tetrahydroquinazolines through one-pot double [3 + 2] dipolar cycloadditions followed by [5 + 1] annulation
title_full_unstemmed Stereoselective synthesis of fused tetrahydroquinazolines through one-pot double [3 + 2] dipolar cycloadditions followed by [5 + 1] annulation
title_short Stereoselective synthesis of fused tetrahydroquinazolines through one-pot double [3 + 2] dipolar cycloadditions followed by [5 + 1] annulation
title_sort stereoselective synthesis of fused tetrahydroquinazolines through one-pot double [3 + 2] dipolar cycloadditions followed by [5 + 1] annulation
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5082442/
https://www.ncbi.nlm.nih.gov/pubmed/27829928
http://dx.doi.org/10.3762/bjoc.12.211
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