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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| Vydané v: | Organic letters Ročník 26; číslo 23; s. 4992 - 4997 |
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| Hlavní autori: | , , , , , , , , , |
| Médium: | Journal Article |
| Jazyk: | English |
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Amer Chemical Soc
14.06.2024
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| ISSN: | 1523-7060, 1523-7052, 1523-7052 |
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| Abstract | 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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| AbstractList | 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.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. A metal-free and mild approach for constructing 5-amino-1,2-selenazole skeletons by NBS/KSeCN-mediated -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. 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. |
| Author | Zhang, Hongbin Shang, Na Tang, E. Yang, Jing Huang, Xuankun Huang, Yi Guo, Jianhua Tang, Qilin Yuan, Caifeng Shen, Yiwen |
| Author_xml | – sequence: 1 givenname: Caifeng surname: Yuan fullname: Yuan, Caifeng organization: Yunnan Univ, Minist Educ, Sch Pharm, Key Lab Med Chem Nat Resources, Kunming 650500, Peoples R China – sequence: 2 givenname: Xuankun surname: Huang fullname: Huang, Xuankun organization: Yunnan Univ, Minist Educ, Sch Pharm, Key Lab Med Chem Nat Resources, Kunming 650500, Peoples R China – sequence: 3 givenname: Jianhua surname: Guo fullname: Guo, Jianhua organization: Yunnan Univ, Minist Educ, Sch Pharm, Key Lab Med Chem Nat Resources, Kunming 650500, Peoples R China – sequence: 4 givenname: Yiwen surname: Shen fullname: Shen, Yiwen organization: Yunnan Univ, Minist Educ, Sch Pharm, Key Lab Med Chem Nat Resources, Kunming 650500, Peoples R China – sequence: 5 givenname: Na surname: Shang fullname: Shang, Na organization: Yunnan Univ, Minist Educ, Sch Pharm, Key Lab Med Chem Nat Resources, Kunming 650500, Peoples R China – sequence: 6 givenname: Qilin surname: Tang fullname: Tang, Qilin organization: Yunnan Univ, Minist Educ, Sch Pharm, Key Lab Med Chem Nat Resources, Kunming 650500, Peoples R China – sequence: 7 givenname: Jing surname: Yang fullname: Yang, Jing organization: Yunnan Univ, Minist Educ, Sch Pharm, Key Lab Med Chem Nat Resources, Kunming 650500, Peoples R China – sequence: 8 givenname: Yi surname: Huang fullname: Huang, Yi organization: Yunnan Univ, Minist Educ, Sch Pharm, Key Lab Med Chem Nat Resources, Kunming 650500, Peoples R China – sequence: 9 givenname: Hongbin orcidid: 0000-0002-2516-2634 surname: Zhang fullname: Zhang, Hongbin email: zhanghb@ynu.edu.cn organization: Yunnan Univ, Minist Educ, Sch Pharm, Key Lab Med Chem Nat Resources, Kunming 650500, Peoples R China – sequence: 10 givenname: E. orcidid: 0000-0003-2382-8479 surname: Tang fullname: Tang, E. email: tange@ynu.edu.cn organization: Yunnan Univ, Minist Educ, Sch Pharm, Key Lab Med Chem Nat Resources, Kunming 650500, Peoples R China |
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| Cites_doi | 10.1002/anie.201505056 10.1021/acs.orglett.0c03674 10.1021/jm401047q 10.1016/j.ccr.2005.04.020 10.1021/acs.jmedchem.6b00986 10.1021/acs.joc.2c02088 10.1021/cr000426w 10.1021/cr0406559 10.1016/j.ejmech.2018.06.007 10.1073/pnas.122061399 10.1016/j.bioorg.2022.106153 10.1246/bcsj.79.25 10.1016/j.poly.2006.09.090 10.1002/ejic.200700501 10.1039/b603199d 10.1039/c5ob01665g 10.1246/bcsj.80.567 10.1038/ncomms2320 10.1021/acs.joc.9b01722 10.1016/j.bmcl.2006.07.085 10.1016/j.ejmech.2007.09.007 10.1016/j.cclet.2022.108043 10.1021/acs.orglett.2c01468 10.1016/j.bmcl.2016.09.050 10.1016/j.comptc.2019.03.007 10.1038/s41586-020-2223-y 10.1002/anie.200600596 10.1016/j.ejmech.2011.12.006 10.1021/acs.joc.0c02286 10.1016/j.tetlet.2016.05.032 10.1074/jbc.M206452200 |
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| Keywords | TARGET THIAZYL RADICALS MECHANISM THIOREDOXIN SUBSTRATE ORGANOSELENIUM COMPOUNDS ISOTHIAZOLES EBSELEN ISOSELENAZOLES DERIVATIVES |
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| Title | Construction of 5-Amino-1,2-Selenazole Scaffolds through N-Selenocyanation/Cyclization of Enaminones Using KSeCN |
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