Gold-catalyzed oxidation of terminal alkynes to glyoxals and their reactions with 2-phenylimidazo[1,2-]pyridines: one-pot synthesis of 1,2-diones
A novel one-pot protocol for the convenient and efficient synthesis of (2-phenylimidazo[1,2- a ]pyridin-3-yl)alkane-1,2-diones ( 3 ) in good yields (32-88%) from 2-phenylimidazo[1,2- a ]pyridines ( 1 ) and terminal alkynes ( 2 ) has been established with a wide range of substrate scope. A tandem rea...
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Published in | Organic & biomolecular chemistry Vol. 19; no. 4; pp. 8735 - 8739 |
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Main Authors | , , , , , , |
Format | Journal Article |
Language | English |
Published |
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Royal Soc Chemistry
20.10.2021
Royal Society of Chemistry |
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Abstract | A novel one-pot protocol for the convenient and efficient synthesis of (2-phenylimidazo[1,2-
a
]pyridin-3-yl)alkane-1,2-diones (
3
) in good yields (32-88%) from 2-phenylimidazo[1,2-
a
]pyridines (
1
) and terminal alkynes (
2
) has been established with a wide range of substrate scope. A tandem reaction sequence containing gold-catalyzed double oxidations of terminal alkynes to generate glyoxals, nucleophilic addition of 2-phenylimidazo[1,2-
a
]pyridines to glyoxals to yield α-hydroxyl ketones, and oxygenation of the α-hydroxyl ketones to afford the final products
3
under air atmosphere is involved in this method. Simple operation, mild reaction conditions, and widely available substrates make this strategy more affordable.
A one-pot procedure with a tandem reaction sequence of oxidative gold catalysis, nucleophilic addition and oxygenation was employed to synthesize 1,2-diones from 2-phenylimidazo[1,2-
a
]pyridines and terminal alkynes in good yields. |
---|---|
AbstractList | A novel one-pot protocol for the convenient and efficient synthesis of (2-phenylimidazo[1,2-
a
]pyridin-3-yl)alkane-1,2-diones (3) in good yields (32–88%) from 2-phenylimidazo[1,2-
a
]pyridines (1) and terminal alkynes (2) has been established with a wide range of substrate scope. A tandem reaction sequence containing gold-catalyzed double oxidations of terminal alkynes to generate glyoxals, nucleophilic addition of 2-phenylimidazo[1,2-
a
]pyridines to glyoxals to yield α-hydroxyl ketones, and oxygenation of the α-hydroxyl ketones to afford the final products 3 under air atmosphere is involved in this method. Simple operation, mild reaction conditions, and widely available substrates make this strategy more affordable. A novel one-pot protocol for the convenient and efficient synthesis of (2-phenylimidazo[1,2-a]pyridin-3-yl)alkane-1,2-diones (3) in good yields (32–88%) from 2-phenylimidazo[1,2-a]pyridines (1) and terminal alkynes (2) has been established with a wide range of substrate scope. A tandem reaction sequence containing gold-catalyzed double oxidations of terminal alkynes to generate glyoxals, nucleophilic addition of 2-phenylimidazo[1,2-a]pyridines to glyoxals to yield α-hydroxyl ketones, and oxygenation of the α-hydroxyl ketones to afford the final products 3 under air atmosphere is involved in this method. Simple operation, mild reaction conditions, and widely available substrates make this strategy more affordable. A novel one-pot protocol for the convenient and efficient synthesis of (2-phenylimidazo[1,2-alpyridin-3-yl)alkane-1,2-diones (3) in good yields (32 88%) from 2-phenylimidazo(1,2-alpyridines (1) and terminal alkynes (2) has been established with a wide range of substrate scope. A tandem reaction sequence containing gold-catalyzed double oxidations of terminal alkynes to generate glyoxals, nucleophilic addition of 2-phenylimidazo[1,2-a]pyridines to glyoxals to yield alpha-hydroxyl ketones, and oxygenation of the alpha-hydroxyl ketones to afford the final products 3 under air atmosphere is involved in this method. Simple operation, mild reaction conditions, and widely available substrates make this strategy more affordable. A novel one-pot protocol for the convenient and efficient synthesis of (2-phenylimidazo[1,2- ]pyridin-3-yl)alkane-1,2-diones (3) in good yields (32-88%) from 2-phenylimidazo[1,2- ]pyridines (1) and terminal alkynes (2) has been established with a wide range of substrate scope. A tandem reaction sequence containing gold-catalyzed double oxidations of terminal alkynes to generate glyoxals, nucleophilic addition of 2-phenylimidazo[1,2- ]pyridines to glyoxals to yield α-hydroxyl ketones, and oxygenation of the α-hydroxyl ketones to afford the final products 3 under air atmosphere is involved in this method. Simple operation, mild reaction conditions, and widely available substrates make this strategy more affordable. A novel one-pot protocol for the convenient and efficient synthesis of (2-phenylimidazo[1,2- a ]pyridin-3-yl)alkane-1,2-diones ( 3 ) in good yields (32-88%) from 2-phenylimidazo[1,2- a ]pyridines ( 1 ) and terminal alkynes ( 2 ) has been established with a wide range of substrate scope. A tandem reaction sequence containing gold-catalyzed double oxidations of terminal alkynes to generate glyoxals, nucleophilic addition of 2-phenylimidazo[1,2- a ]pyridines to glyoxals to yield α-hydroxyl ketones, and oxygenation of the α-hydroxyl ketones to afford the final products 3 under air atmosphere is involved in this method. Simple operation, mild reaction conditions, and widely available substrates make this strategy more affordable. A one-pot procedure with a tandem reaction sequence of oxidative gold catalysis, nucleophilic addition and oxygenation was employed to synthesize 1,2-diones from 2-phenylimidazo[1,2- a ]pyridines and terminal alkynes in good yields. |
Author | Zhou, Xuefeng Wang, Junfeng Liu, Yonghong Liao, Shengrong Lin, Xiuping Yang, Bin Xu, Huayan |
AuthorAffiliation | South China Sea Institute of Oceanology Chinese Academy of Sciences Guangdong Key Laboratory of Marine Materia Medica SCSIO Sanya Institute of Oceanology Southern Marine Science and Engineering Guangdong Laboratory (Guangzhou) CAS Key Laboratory of Tropical Marine Bio-Resources and Ecology Research Center for Marine Microbes |
AuthorAffiliation_xml | – name: Sanya Institute of Oceanology – name: CAS Key Laboratory of Tropical Marine Bio-Resources and Ecology – name: Chinese Academy of Sciences – name: Guangdong Key Laboratory of Marine Materia Medica – name: SCSIO – name: Southern Marine Science and Engineering Guangdong Laboratory (Guangzhou) – name: Research Center for Marine Microbes – name: South China Sea Institute of Oceanology |
Author_xml | – sequence: 1 givenname: Shengrong surname: Liao fullname: Liao, Shengrong – sequence: 2 givenname: Huayan surname: Xu fullname: Xu, Huayan – sequence: 3 givenname: Bin surname: Yang fullname: Yang, Bin – sequence: 4 givenname: Junfeng surname: Wang fullname: Wang, Junfeng – sequence: 5 givenname: Xuefeng surname: Zhou fullname: Zhou, Xuefeng – sequence: 6 givenname: Xiuping surname: Lin fullname: Lin, Xiuping – sequence: 7 givenname: Yonghong surname: Liu fullname: Liu, Yonghong |
BackLink | https://www.ncbi.nlm.nih.gov/pubmed/34476433$$D View this record in MEDLINE/PubMed |
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Cites_doi | 10.1002/jbt.22663 10.1039/c4cc08495k 10.1021/acs.orglett.9b01297 10.1039/c7ob00883j 10.3390/molecules25143161 10.1021/acsomega.8b03581 10.1016/j.tet.2015.12.012 10.1039/c0md00116c 10.1039/c8cc07063f 10.1007/s11030-020-10137-8 10.1093/jpp/rgaa070 10.1016/j.bmc.2020.115574 10.1039/c9ob00812h 10.3762/bjoc.16.94 10.1002/anie.200907291 10.1016/j.bbrc.2018.07.039 10.1039/c7ob01778b 10.1021/ol200270t 10.1002/adsc.201500803 10.1021/acs.joc.6b02091 10.1002/adsc.201601431 10.1002/ejoc.201900108 10.1021/acs.joc.0c00674 10.1016/j.bmc.2011.05.062 10.1016/j.bmcl.2019.08.013 10.1021/acs.joc.5b02417 10.1007/s10593-017-2066-0 10.1002/ejoc.201600694 10.1021/acs.jmedchem.9b01910 10.1016/j.bmc.2011.06.012 10.1021/acs.joc.9b02785 10.1021/acs.jmedchem.0c02163 10.1016/j.tet.2018.07.027 10.1021/ol501136e 10.1002/chem.201300518 10.1021/acschemneuro.6b00432 10.1021/acsomega.9b00716 10.1039/c4ra15835k 10.1039/c9ob00095j 10.1002/ejoc.201200107 10.1055/s-0033-1338804 10.1039/C7OB00883J 10.1039/C4RA15835K 10.1039/C8CC07063F 10.1039/C7OB01778B 10.1039/C9OB00812H 10.1039/C9OB00095J 10.1039/C4CC08495K 10.2165/0023210-200822120-00005 10.2165/00023210-200519010-00008 |
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Keywords | ROUTE ZOLPIDEM DICARBONYLATION EFFICIENT DERIVATIVES IMIDAZOHETEROCYCLES |
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Snippet | A novel one-pot protocol for the convenient and efficient synthesis of (2-phenylimidazo[1,2-
a
]pyridin-3-yl)alkane-1,2-diones (
3
) in good yields (32-88%)... A novel one-pot protocol for the convenient and efficient synthesis of (2-phenylimidazo[1,2-alpyridin-3-yl)alkane-1,2-diones (3) in good yields (32 88%) from... A novel one-pot protocol for the convenient and efficient synthesis of (2-phenylimidazo[1,2- ]pyridin-3-yl)alkane-1,2-diones (3) in good yields (32-88%) from... A novel one-pot protocol for the convenient and efficient synthesis of (2-phenylimidazo[1,2- a ]pyridin-3-yl)alkane-1,2-diones (3) in good yields (32–88%) from... A novel one-pot protocol for the convenient and efficient synthesis of (2-phenylimidazo[1,2-a]pyridin-3-yl)alkane-1,2-diones (3) in good yields (32–88%) from... |
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SubjectTerms | Alkanes Alkynes Cascade chemical reactions Chemical reactions Chemistry Chemistry, Organic Gold Ketones Nucleotide sequence Oxidation Oxygenation Physical Sciences Pyridines Science & Technology Substrates |
Title | Gold-catalyzed oxidation of terminal alkynes to glyoxals and their reactions with 2-phenylimidazo[1,2-]pyridines: one-pot synthesis of 1,2-diones |
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