Microwave mediated hydrogen deuterium exchange: a rapid synthesis of 2H-substituted benzimidazole
Aromatic deuterium compounds were prepared from the unlabeled parent compounds under microwave irradiation. This novel methodology was applied to the deuterium substituted benzimidazole derivative. Deuterium aromatic substituted compounds were prepared by microwave irradiation of the parent unlabele...
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Published in | Tetrahedron letters Vol. 46; no. 31; pp. 5195 - 5197 |
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Main Authors | , |
Format | Journal Article |
Language | English |
Published |
Elsevier Ltd
01.08.2005
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Abstract | Aromatic deuterium compounds were prepared from the unlabeled parent compounds under microwave irradiation. This novel methodology was applied to the deuterium substituted benzimidazole derivative.
Deuterium aromatic substituted compounds were prepared by microwave irradiation of the parent unlabeled compounds in the presence of deuterium oxide and deuterium chloride. The percentage of deuterium incorporation was investigated under various reaction conditions. A rapid synthesis of
2H-substituted benzimidazole under microwave irradiation is described. |
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AbstractList | Aromatic deuterium compounds were prepared from the unlabeled parent compounds under microwave irradiation. This novel methodology was applied to the deuterium substituted benzimidazole derivative.
Deuterium aromatic substituted compounds were prepared by microwave irradiation of the parent unlabeled compounds in the presence of deuterium oxide and deuterium chloride. The percentage of deuterium incorporation was investigated under various reaction conditions. A rapid synthesis of
2H-substituted benzimidazole under microwave irradiation is described. |
Author | Surber, Bruce W. Vaidyanathan, Srirajan |
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CitedBy_id | crossref_primary_10_1002_ange_200700039 crossref_primary_10_1002_ajoc_202200662 crossref_primary_10_1002_ejoc_201500192 crossref_primary_10_1016_j_tetlet_2014_07_071 crossref_primary_10_1002_anie_200700039 crossref_primary_10_1021_ja300655f crossref_primary_10_1016_j_molcata_2006_04_071 crossref_primary_10_1016_j_bmc_2009_01_049 crossref_primary_10_1016_j_tetlet_2017_03_045 crossref_primary_10_1021_ol801763j crossref_primary_10_1246_bcsj_81_278 crossref_primary_10_1016_j_tet_2010_12_007 crossref_primary_10_1039_c2ob25157d crossref_primary_10_1039_C4QO00333K crossref_primary_10_3389_fnut_2020_619921 |
Cites_doi | 10.1002/anie.200400655 10.1124/dmd.32.6.647 10.1002/jlcr.2580340308 10.1039/b005724j 10.1016/j.tetasy.2004.11.040 10.1002/jlcr.2580150176 10.1016/j.tetlet.2003.12.002 10.1016/j.tetlet.2005.01.025 10.1351/pac200173010193 10.1016/S0040-4020(01)01216-9 10.1021/jm030505a |
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References | bib9 Anto, Getvoldsen, Harding, Jones, Lu, Russell, Cioffi, Bell, Le, Koves (bib5) 2000; 16 bib7 Freed, Murphy (bib2) 1978 Varma, Varma (bib4) 2001; 73 bib8 Walsky, Opbach (bib1) 2004; 32 Kim, Varma, Varma, Kappe, Bose, Ganguly, Manhas, Vaidyanathan, Bhattacharjee, Rumthao, Sharma (bib3) 2005; 46 bib6 Cowart, Latshaw, Bhatia, Daanen, Rohde, Nelson, Patel, Kolasa, Nakane, Uchic, Miller, Terranova, Chang, Donnelly-Roberts, Namovic, Hollingsworth, Martino, Lynch, Sullivan, Hsieh, Moreland, Brioni, Stewart (bib10) 2004; 47 Varma (10.1016/j.tetlet.2005.05.110_bib4_1) 2001; 73 Cioffi (10.1016/j.tetlet.2005.05.110_bib5_2) 2005; 16 Walsky (10.1016/j.tetlet.2005.05.110_bib1) 2004; 32 Anto (10.1016/j.tetlet.2005.05.110_bib5_1) 2000 Kim (10.1016/j.tetlet.2005.05.110_bib3_1) 2005; 46 Cowart (10.1016/j.tetlet.2005.05.110_bib10) 2004; 47 Bose (10.1016/j.tetlet.2005.05.110_bib3_4) 2004; 45 Koves (10.1016/j.tetlet.2005.05.110_bib5_3) 1994; 34 Kappe (10.1016/j.tetlet.2005.05.110_bib3_3) 2004; 43 Freed (10.1016/j.tetlet.2005.05.110_bib2) 1978 Varma (10.1016/j.tetlet.2005.05.110_bib3_2) 2002 Varma (10.1016/j.tetlet.2005.05.110_bib4_2) 2002; 58 |
References_xml | – volume: 46 start-page: 1467 year: 2005 ident: bib3 article-title: Organic Synthesis Using Microwave and Supported Reagents publication-title: Tetrahedron Lett. contributor: fullname: Sharma – volume: 47 start-page: 3853 year: 2004 ident: bib10 publication-title: J. Med. Chem. contributor: fullname: Stewart – ident: bib6 – ident: bib7 – volume: 32 start-page: 647 year: 2004 ident: bib1 publication-title: Drug Metab. Dispos. contributor: fullname: Opbach – ident: bib8 – ident: bib9 – volume: 16 start-page: 2208 year: 2000 ident: bib5 publication-title: J. Chem. Soc., Perkin Trans. 2 contributor: fullname: Koves – volume: 73 start-page: 193 year: 2001 ident: bib4 publication-title: Pure Appl. Chem. contributor: fullname: Varma – start-page: 637 year: 1978 ident: bib2 publication-title: J. Labelled Compd. Radiopharm. contributor: fullname: Murphy – volume: 43 start-page: 6250 year: 2004 ident: 10.1016/j.tetlet.2005.05.110_bib3_3 publication-title: Angew. Chem., Int. Ed. doi: 10.1002/anie.200400655 contributor: fullname: Kappe – volume: 32 start-page: 647 year: 2004 ident: 10.1016/j.tetlet.2005.05.110_bib1 publication-title: Drug Metab. Dispos. doi: 10.1124/dmd.32.6.647 contributor: fullname: Walsky – start-page: 181 year: 2002 ident: 10.1016/j.tetlet.2005.05.110_bib3_2 article-title: Organic Synthesis Using Microwave and Supported Reagents contributor: fullname: Varma – volume: 34 start-page: 255 year: 1994 ident: 10.1016/j.tetlet.2005.05.110_bib5_3 publication-title: J. Labelled Compd. Radiopharm. doi: 10.1002/jlcr.2580340308 contributor: fullname: Koves – start-page: 2208 year: 2000 ident: 10.1016/j.tetlet.2005.05.110_bib5_1 publication-title: J. Chem. Soc., Perkin Trans. 2 doi: 10.1039/b005724j contributor: fullname: Anto – volume: 16 start-page: 471 year: 2005 ident: 10.1016/j.tetlet.2005.05.110_bib5_2 publication-title: Tetrahedron: Asymmetry doi: 10.1016/j.tetasy.2004.11.040 contributor: fullname: Cioffi – start-page: 637 year: 1978 ident: 10.1016/j.tetlet.2005.05.110_bib2 publication-title: J. Labelled Compd. Radiopharm. doi: 10.1002/jlcr.2580150176 contributor: fullname: Freed – volume: 45 start-page: 1179 year: 2004 ident: 10.1016/j.tetlet.2005.05.110_bib3_4 publication-title: Tetrahedron Lett. doi: 10.1016/j.tetlet.2003.12.002 contributor: fullname: Bose – volume: 46 start-page: 1467 year: 2005 ident: 10.1016/j.tetlet.2005.05.110_bib3_1 publication-title: Tetrahedron Lett. doi: 10.1016/j.tetlet.2005.01.025 contributor: fullname: Kim – volume: 73 start-page: 193 year: 2001 ident: 10.1016/j.tetlet.2005.05.110_bib4_1 publication-title: Pure Appl. Chem. doi: 10.1351/pac200173010193 contributor: fullname: Varma – volume: 58 start-page: 1235 year: 2002 ident: 10.1016/j.tetlet.2005.05.110_bib4_2 publication-title: Tetrahedron doi: 10.1016/S0040-4020(01)01216-9 contributor: fullname: Varma – volume: 47 start-page: 3853 year: 2004 ident: 10.1016/j.tetlet.2005.05.110_bib10 publication-title: J. Med. Chem. doi: 10.1021/jm030505a contributor: fullname: Cowart |
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Title | Microwave mediated hydrogen deuterium exchange: a rapid synthesis of 2H-substituted benzimidazole |
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