Exploring chemical diversity via a modular reaction pairing strategy

The efficient synthesis of an 80-member library of unique benzoxathiazocine 1,1-dioxides by a microwave-assisted, intermolecular nucleophilic aromatic substitution (S(N)Ar) diversification pathway is reported. Eight benzofused sultam cores were generated by means of a sulfonylation/S(N)Ar/Mitsunobu...

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Autores principales: Loh, Joanna K, Yoon, Sun Young, Samarakoon, Thiwanka B, Rolfe, Alan, Porubsky, Patrick, Neuenswander, Benjamin, Lushington, Gerald H, Hanson, Paul R
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2012
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3458752/
https://www.ncbi.nlm.nih.gov/pubmed/23019462
http://dx.doi.org/10.3762/bjoc.8.147
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author Loh, Joanna K
Yoon, Sun Young
Samarakoon, Thiwanka B
Rolfe, Alan
Porubsky, Patrick
Neuenswander, Benjamin
Lushington, Gerald H
Hanson, Paul R
author_facet Loh, Joanna K
Yoon, Sun Young
Samarakoon, Thiwanka B
Rolfe, Alan
Porubsky, Patrick
Neuenswander, Benjamin
Lushington, Gerald H
Hanson, Paul R
author_sort Loh, Joanna K
collection PubMed
description The efficient synthesis of an 80-member library of unique benzoxathiazocine 1,1-dioxides by a microwave-assisted, intermolecular nucleophilic aromatic substitution (S(N)Ar) diversification pathway is reported. Eight benzofused sultam cores were generated by means of a sulfonylation/S(N)Ar/Mitsunobu reaction pairing protocol, and subsequently diversified by intermolecular S(N)Ar with ten chiral, non-racemic amine/amino alcohol building blocks. Computational analyses were employed to explore and evaluate the chemical diversity of the library.
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spelling pubmed-34587522012-09-27 Exploring chemical diversity via a modular reaction pairing strategy Loh, Joanna K Yoon, Sun Young Samarakoon, Thiwanka B Rolfe, Alan Porubsky, Patrick Neuenswander, Benjamin Lushington, Gerald H Hanson, Paul R Beilstein J Org Chem Full Research Paper The efficient synthesis of an 80-member library of unique benzoxathiazocine 1,1-dioxides by a microwave-assisted, intermolecular nucleophilic aromatic substitution (S(N)Ar) diversification pathway is reported. Eight benzofused sultam cores were generated by means of a sulfonylation/S(N)Ar/Mitsunobu reaction pairing protocol, and subsequently diversified by intermolecular S(N)Ar with ten chiral, non-racemic amine/amino alcohol building blocks. Computational analyses were employed to explore and evaluate the chemical diversity of the library. Beilstein-Institut 2012-08-15 /pmc/articles/PMC3458752/ /pubmed/23019462 http://dx.doi.org/10.3762/bjoc.8.147 Text en Copyright © 2012, Loh et al. https://creativecommons.org/licenses/by/2.0https://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/2.0), 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
Loh, Joanna K
Yoon, Sun Young
Samarakoon, Thiwanka B
Rolfe, Alan
Porubsky, Patrick
Neuenswander, Benjamin
Lushington, Gerald H
Hanson, Paul R
Exploring chemical diversity via a modular reaction pairing strategy
title Exploring chemical diversity via a modular reaction pairing strategy
title_full Exploring chemical diversity via a modular reaction pairing strategy
title_fullStr Exploring chemical diversity via a modular reaction pairing strategy
title_full_unstemmed Exploring chemical diversity via a modular reaction pairing strategy
title_short Exploring chemical diversity via a modular reaction pairing strategy
title_sort exploring chemical diversity via a modular reaction pairing strategy
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3458752/
https://www.ncbi.nlm.nih.gov/pubmed/23019462
http://dx.doi.org/10.3762/bjoc.8.147
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