Copper-Catalyzed Diversity-Oriented Synthesis (DOS) of 4-Amino-2H-chromen-2-imines: Application of Kemp Elimination toward O-Heterocycles

[Image: see text] We report herein a copper-catalyzed sequential multicomponent reaction of benzo[d]isoxazoles with terminal alkynes and sulfonyl azides, which produced divergent 4-amino-2H-chromen-2-imines with excellent chemical selectivity. The reaction tolerated a broad range of functional group...

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Autores principales: Chen, Zhiyuan, Han, Cuifen, Fan, Congbin, Liu, Gang, Pu, Shouzhi
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2018
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6644361/
https://www.ncbi.nlm.nih.gov/pubmed/31458953
http://dx.doi.org/10.1021/acsomega.8b01179
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author Chen, Zhiyuan
Han, Cuifen
Fan, Congbin
Liu, Gang
Pu, Shouzhi
author_facet Chen, Zhiyuan
Han, Cuifen
Fan, Congbin
Liu, Gang
Pu, Shouzhi
author_sort Chen, Zhiyuan
collection PubMed
description [Image: see text] We report herein a copper-catalyzed sequential multicomponent reaction of benzo[d]isoxazoles with terminal alkynes and sulfonyl azides, which produced divergent 4-amino-2H-chromen-2-imines with excellent chemical selectivity. The reaction tolerated a broad range of functional groups, and released only N(2) as the sole byproduct. The sulfonyl imino group could be removed to give biologically active free 4-amino-2H-chromenone in good yield.
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spelling pubmed-66443612019-08-27 Copper-Catalyzed Diversity-Oriented Synthesis (DOS) of 4-Amino-2H-chromen-2-imines: Application of Kemp Elimination toward O-Heterocycles Chen, Zhiyuan Han, Cuifen Fan, Congbin Liu, Gang Pu, Shouzhi ACS Omega [Image: see text] We report herein a copper-catalyzed sequential multicomponent reaction of benzo[d]isoxazoles with terminal alkynes and sulfonyl azides, which produced divergent 4-amino-2H-chromen-2-imines with excellent chemical selectivity. The reaction tolerated a broad range of functional groups, and released only N(2) as the sole byproduct. The sulfonyl imino group could be removed to give biologically active free 4-amino-2H-chromenone in good yield. American Chemical Society 2018-07-23 /pmc/articles/PMC6644361/ /pubmed/31458953 http://dx.doi.org/10.1021/acsomega.8b01179 Text en Copyright © 2018 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 Chen, Zhiyuan
Han, Cuifen
Fan, Congbin
Liu, Gang
Pu, Shouzhi
Copper-Catalyzed Diversity-Oriented Synthesis (DOS) of 4-Amino-2H-chromen-2-imines: Application of Kemp Elimination toward O-Heterocycles
title Copper-Catalyzed Diversity-Oriented Synthesis (DOS) of 4-Amino-2H-chromen-2-imines: Application of Kemp Elimination toward O-Heterocycles
title_full Copper-Catalyzed Diversity-Oriented Synthesis (DOS) of 4-Amino-2H-chromen-2-imines: Application of Kemp Elimination toward O-Heterocycles
title_fullStr Copper-Catalyzed Diversity-Oriented Synthesis (DOS) of 4-Amino-2H-chromen-2-imines: Application of Kemp Elimination toward O-Heterocycles
title_full_unstemmed Copper-Catalyzed Diversity-Oriented Synthesis (DOS) of 4-Amino-2H-chromen-2-imines: Application of Kemp Elimination toward O-Heterocycles
title_short Copper-Catalyzed Diversity-Oriented Synthesis (DOS) of 4-Amino-2H-chromen-2-imines: Application of Kemp Elimination toward O-Heterocycles
title_sort copper-catalyzed diversity-oriented synthesis (dos) of 4-amino-2h-chromen-2-imines: application of kemp elimination toward o-heterocycles
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6644361/
https://www.ncbi.nlm.nih.gov/pubmed/31458953
http://dx.doi.org/10.1021/acsomega.8b01179
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