Construction of 5‑Amino-1,2-Selenazole Scaffolds through N‑Selenocyanation/Cyclization of Enaminones Using KSeCN

A metal-free and mild approach for constructing 5-amino-1,2-selenazole skeletons by NBS/KSeCN-mediated N-selenocyanation and nucleophilic cyclization of β-enaminones has been developed. Various isoselenazole compounds and the isoselenazolyl derivatives of anti-inflammatory medicines, including isose...

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Veröffentlicht in:	Organic letters 2024-06, Vol.26 (23), p.4992-4997
Hauptverfasser:	Yuan, Caifeng, Huang, Xuankun, Guo, Jianhua, Shen, Yiwen, Shang, Na, Tang, Qilin, Yang, Jing, Huang, Yi, Zhang, Hongbin, Tang, E
Format:	Artikel
Sprache:	eng
Schlagworte:	heterocyclic compounds ibuprofen Lewis bases
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container_title	Organic letters
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creator	Yuan, Caifeng Huang, Xuankun Guo, Jianhua Shen, Yiwen Shang, Na Tang, Qilin Yang, Jing Huang, Yi Zhang, Hongbin Tang, E
description	A metal-free and mild approach for constructing 5-amino-1,2-selenazole skeletons by NBS/KSeCN-mediated N-selenocyanation and nucleophilic cyclization of β-enaminones has been developed. Various isoselenazole compounds and the isoselenazolyl derivatives of anti-inflammatory medicines, including isosepac, oxaprozin, and ibuprofen, have been obtained with good yields. This efficient, “one-pot”, and atomic economy strategy may represent an alternative route for the construction of a 1,2-selenazole framework via the “+SeCN” pathway and provide new access to heterocycles containing a Se–N bond.
doi_str_mv	10.1021/acs.orglett.4c01655
format	Article
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subjects	heterocyclic compounds ibuprofen Lewis bases
title	Construction of 5‑Amino-1,2-Selenazole Scaffolds through N‑Selenocyanation/Cyclization of Enaminones Using KSeCN
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