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 beta-enaminones has been developed. Various isoselenazole compounds and the isoselenazolyl derivatives of anti-inflammatory medicines, including is...

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Published in:Organic letters Vol. 26; no. 23; pp. 4992 - 4997
Main Authors: Yuan, Caifeng, Huang, Xuankun, Guo, Jianhua, Shen, Yiwen, Shang, Na, Tang, Qilin, Yang, Jing, Huang, Yi, Zhang, Hongbin, Tang, E.
Format: Journal Article
Language:English
Published: WASHINGTON Amer Chemical Soc 14.06.2024
Subjects:
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
TARGET
THIAZYL RADICALS
MECHANISM
THIOREDOXIN
SUBSTRATE
ORGANOSELENIUM COMPOUNDS
ISOTHIAZOLES
EBSELEN
ISOSELENAZOLES
DERIVATIVES
ISSN:1523-7060, 1523-7052, 1523-7052
Online Access:Get more information
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Summary:A metal-free and mild approach for constructing 5-amino-1,2-selenazole skeletons by NBS/KSeCN-mediated N-selenocyanation and nucleophilic cyclization of beta-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.
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content type line 23
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.4c01655