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Modular, One-Pot, Sequential Aziridine Ring Opening–S(N)Ar Strategy to 7-, 10-, and 11-Membered Benzo-Fused Sultams

[Image: see text] The generation of common and stereochemically rich medium-sized benzo-fused sultams via complementary pairing of heretofore-unknown (o-fluoroaryl)sulfonyl aziridine building blocks with an array of amino alcohols/amines in a modular one-pot, sequential protocol using an aziridine r...

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Autores principales: Loh, Joanna K., Asad, Naeem, Samarakoon, Thiwanka B., Hanson, Paul R.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2015
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4943336/
https://www.ncbi.nlm.nih.gov/pubmed/26446396
http://dx.doi.org/10.1021/acs.joc.5b01429
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author Loh, Joanna K.
Asad, Naeem
Samarakoon, Thiwanka B.
Hanson, Paul R.
author_facet Loh, Joanna K.
Asad, Naeem
Samarakoon, Thiwanka B.
Hanson, Paul R.
author_sort Loh, Joanna K.
collection PubMed
description [Image: see text] The generation of common and stereochemically rich medium-sized benzo-fused sultams via complementary pairing of heretofore-unknown (o-fluoroaryl)sulfonyl aziridine building blocks with an array of amino alcohols/amines in a modular one-pot, sequential protocol using an aziridine ring opening and intramolecular nucleophilic aromatic substitution is reported. The strategy employs a variety of amino alcohols/amines and proceeds with 6 + 4/6 + 5 and 6 + 1 cycloetherification pathways in a highly chemo- and regioselective fashion to obtain skeletally and structurally diverse, polycyclic, 10- to 11- and 7-membered benzo-fused sultams for broad-scale screening.
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spelling pubmed-49433362016-10-08 Modular, One-Pot, Sequential Aziridine Ring Opening–S(N)Ar Strategy to 7-, 10-, and 11-Membered Benzo-Fused Sultams Loh, Joanna K. Asad, Naeem Samarakoon, Thiwanka B. Hanson, Paul R. J Org Chem [Image: see text] The generation of common and stereochemically rich medium-sized benzo-fused sultams via complementary pairing of heretofore-unknown (o-fluoroaryl)sulfonyl aziridine building blocks with an array of amino alcohols/amines in a modular one-pot, sequential protocol using an aziridine ring opening and intramolecular nucleophilic aromatic substitution is reported. The strategy employs a variety of amino alcohols/amines and proceeds with 6 + 4/6 + 5 and 6 + 1 cycloetherification pathways in a highly chemo- and regioselective fashion to obtain skeletally and structurally diverse, polycyclic, 10- to 11- and 7-membered benzo-fused sultams for broad-scale screening. American Chemical Society 2015-10-08 2015-10-16 /pmc/articles/PMC4943336/ /pubmed/26446396 http://dx.doi.org/10.1021/acs.joc.5b01429 Text en Copyright © 2015 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Loh, Joanna K.
Asad, Naeem
Samarakoon, Thiwanka B.
Hanson, Paul R.
Modular, One-Pot, Sequential Aziridine Ring Opening–S(N)Ar Strategy to 7-, 10-, and 11-Membered Benzo-Fused Sultams
title Modular, One-Pot, Sequential Aziridine Ring Opening–S(N)Ar Strategy to 7-, 10-, and 11-Membered Benzo-Fused Sultams
title_full Modular, One-Pot, Sequential Aziridine Ring Opening–S(N)Ar Strategy to 7-, 10-, and 11-Membered Benzo-Fused Sultams
title_fullStr Modular, One-Pot, Sequential Aziridine Ring Opening–S(N)Ar Strategy to 7-, 10-, and 11-Membered Benzo-Fused Sultams
title_full_unstemmed Modular, One-Pot, Sequential Aziridine Ring Opening–S(N)Ar Strategy to 7-, 10-, and 11-Membered Benzo-Fused Sultams
title_short Modular, One-Pot, Sequential Aziridine Ring Opening–S(N)Ar Strategy to 7-, 10-, and 11-Membered Benzo-Fused Sultams
title_sort modular, one-pot, sequential aziridine ring opening–s(n)ar strategy to 7-, 10-, and 11-membered benzo-fused sultams
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4943336/
https://www.ncbi.nlm.nih.gov/pubmed/26446396
http://dx.doi.org/10.1021/acs.joc.5b01429
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