Zirconium-catalysed N-acylation of lactams using unactivated carboxylic acids
[Display omitted] •New method for the catalytic N-acylation of lactams with carboxylic acids.•Screening of Lewis acid catalysts for N-acylation of pyroglutamic acid methyl ester.•Yields up to 97% were reached with 10 mol% Zr(propoxide)4.•Substrate scope was investigated; with 57–97% yield achieved.•...
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| Published in: | Tetrahedron letters Vol. 59; no. 17; pp. 1646 - 1650 |
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| Main Authors: | , , |
| Format: | Journal Article |
| Language: | English |
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Elsevier Ltd
25.04.2018
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| ISSN: | 0040-4039, 1873-3581 |
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| Abstract | [Display omitted]
•New method for the catalytic N-acylation of lactams with carboxylic acids.•Screening of Lewis acid catalysts for N-acylation of pyroglutamic acid methyl ester.•Yields up to 97% were reached with 10 mol% Zr(propoxide)4.•Substrate scope was investigated; with 57–97% yield achieved.•The drug aniracetam can be produced in 84% yield.
A large number of chemicals including surfactants, nootropic drugs and pesticides contain an N-acylated lactam moiety in their molecular structure. In this work, the direct, catalytic N-acylation of a number of lactams with various unactivated carboxylic acids is reported. Several Lewis acid catalysts were evaluated for their activity in the N-acylation of pyroglutamic acid methyl ester with palmitic acid; the highest activities were observed for zirconium-based catalysts. Yields of up to 97% were obtained utilising 10 mol% Zr(propoxide)4 in mesitylene at reflux temperature, but ZrOCl2·8H2O was determined as the most stable catalyst. The substrate scope was investigated and a number of lactam-carboxylic acid combinations were successfully converted into the desired products in 57–97% yield. This method provides an alternative synthetic pathway towards the drug aniracetam, which can be produced in 84% yield. A plausible catalytic mechanism is presented based on kinetic experiments. |
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| AbstractList | [Display omitted]
•New method for the catalytic N-acylation of lactams with carboxylic acids.•Screening of Lewis acid catalysts for N-acylation of pyroglutamic acid methyl ester.•Yields up to 97% were reached with 10 mol% Zr(propoxide)4.•Substrate scope was investigated; with 57–97% yield achieved.•The drug aniracetam can be produced in 84% yield.
A large number of chemicals including surfactants, nootropic drugs and pesticides contain an N-acylated lactam moiety in their molecular structure. In this work, the direct, catalytic N-acylation of a number of lactams with various unactivated carboxylic acids is reported. Several Lewis acid catalysts were evaluated for their activity in the N-acylation of pyroglutamic acid methyl ester with palmitic acid; the highest activities were observed for zirconium-based catalysts. Yields of up to 97% were obtained utilising 10 mol% Zr(propoxide)4 in mesitylene at reflux temperature, but ZrOCl2·8H2O was determined as the most stable catalyst. The substrate scope was investigated and a number of lactam-carboxylic acid combinations were successfully converted into the desired products in 57–97% yield. This method provides an alternative synthetic pathway towards the drug aniracetam, which can be produced in 84% yield. A plausible catalytic mechanism is presented based on kinetic experiments. A large number of chemicals including surfactants, nootropic drugs and pesticides contain an N-acylated lactam moiety in their molecular structure. In this work, the direct, catalytic N-acylation of a number of lactams with various unactivated carboxylic acids is reported. Several Lewis acid catalysts were evaluated for their activity in the N-acylation of pyroglutamic acid methyl ester with palmitic acid; the highest activities were observed for zirconium-based catalysts. Yields of up to 97% were obtained utilising 10 mol% Zr(propoxide)4 in mesitylene at reflux temperature, but ZrOCl2·8H2O was determined as the most stable catalyst. The substrate scope was investigated and a number of lactam-carboxylic acid combinations were successfully converted into the desired products in 57–97% yield. This method provides an alternative synthetic pathway towards the drug aniracetam, which can be produced in 84% yield. A plausible catalytic mechanism is presented based on kinetic experiments. A large number of chemicals including surfactants, nootropic drugs and pesticides contain an N-acylated lactam moiety in their molecular structure. In this work, the direct, catalytic N-acylation of a number of lactams with various unactivated carboxylic acids is reported. Several Lewis acid catalysts were evaluated for their activity in the N-acylation of pyroglutamic acid methyl ester with palmitic acid; the highest activities were observed for zirconium-based catalysts. Yields of up to 97% were obtained utilising 10 mol% Zr(propoxide)(4) in mesitylene at reflux temperature, but ZrOCl2 center dot 8H(2)O was determined as the most stable catalyst. The substrate scope was investigated and a number of lactam-carboxylic acid combinations were successfully converted into the desired products in 57-97% yield. This method provides an alternative synthetic pathway towards the drug aniracetam, which can be produced in 84% yield. A plausible catalytic mechanism is presented based on kinetic experiments. (C) 2018 Published by Elsevier Ltd. |
| Author | Hulsbosch, Joris Claes, Laurens De Vos, Dirk E. |
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| Keywords | Zirconyl chloride Catalysis Aniracetam Lactam N-Acylation CHEMISTRY DISORDERS CHLORIDE |
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| References | Nikoofar, Khademi (b0070) 2016; 42 Kott KL, Willey AD, Miracle GS, Burckett-St.Laurent JC, WO Pat 1996016156A1, 1996. Constable, Dunn, Hayler (b0030) 2007; 9 Dixit, Tandel, Rajappa (b0060) 1994; 35 Vorhis F, VJACKS Nootropics, Inc., Univ. Calif. Berkeley, 1999, 216, 371–4386. Lundberg, Tinnis, Selander, Adolfsson (b0040) 2014; 43 El-Faham, Albericio (b0035) 2011; 111 Paul, Chadha, Vasisht (b0075) 1968; 16 Nakamura (b0010) 2002; 8 Li, Tsai, Damu (b0015) 2007; 55 Sakakira, Matsui (b0005) 1973; 37 Willey AD, Miller LE, US Pat 5510477, 1996. Yang, Bumbu, Li (b0050) 2012; 134 Malykh, Sadaie (b0080) 2010; 70 Talukdar, Saikia, Thakur (b0065) 2011; 11 Kumar, Bachhawat (b0055) 2012; 102 Zhang, Hong (b0045) 2012; 14 Dixit (10.1016/j.tetlet.2018.03.047_b0060) 1994; 35 10.1016/j.tetlet.2018.03.047_b0025 Talukdar (10.1016/j.tetlet.2018.03.047_b0065) 2011; 11 Yang (10.1016/j.tetlet.2018.03.047_b0050) 2012; 134 Nakamura (10.1016/j.tetlet.2018.03.047_b0010) 2002; 8 Constable (10.1016/j.tetlet.2018.03.047_b0030) 2007; 9 Nikoofar (10.1016/j.tetlet.2018.03.047_b0070) 2016; 42 Li (10.1016/j.tetlet.2018.03.047_b0015) 2007; 55 El-Faham (10.1016/j.tetlet.2018.03.047_b0035) 2011; 111 Lundberg (10.1016/j.tetlet.2018.03.047_b0040) 2014; 43 Zhang (10.1016/j.tetlet.2018.03.047_b0045) 2012; 14 Sakakira (10.1016/j.tetlet.2018.03.047_b0005) 1973; 37 Malykh (10.1016/j.tetlet.2018.03.047_b0080) 2010; 70 10.1016/j.tetlet.2018.03.047_b0085 Paul (10.1016/j.tetlet.2018.03.047_b0075) 1968; 16 Kumar (10.1016/j.tetlet.2018.03.047_b0055) 2012; 102 10.1016/j.tetlet.2018.03.047_b0020 DIXIT, AN (WOS:A1994PC53300046) 1994; 35 Constable, DJC (WOS:000246802600012) 2007; 9 Malykh, AG (WOS:000275827700004) 2010; 70 Zhang, J (WOS:000308390000090) 2012; 14 Talukdar, D (WOS:000291789200022) 2011 Nikoofar, K (WOS:000373617700001) 2016; 42 Lundberg, H (WOS:000333330200017) 2014; 43 (000430524700010.1) 1996 Kumar, A (WOS:000299857300022) 2012; 102 El-Faham, A (WOS:000296685200002) 2011; 111 Yang, X (WOS:000310103800057) 2012; 134 SAKAKIBA.M (WOS:A1973P691200028) 1973; 37 Nakamura, K (WOS:000176291100004) 2002; 8 PAUL, RC (WOS:A1968C087600012) 1968; 16 (000430524700010.2) 1996 Li, CY (WOS:000250794100017) 2007; 55 |
| References_xml | – volume: 55 start-page: 9436 year: 2007 end-page: 9442 ident: b0015 publication-title: J Agric Food Chem – volume: 70 start-page: 287 year: 2010 end-page: 312 ident: b0080 publication-title: Drugs – volume: 35 start-page: 6133 year: 1994 end-page: 6134 ident: b0060 publication-title: Tetrahedron Lett – volume: 37 start-page: 911 year: 1973 end-page: 914 ident: b0005 publication-title: Agric Biol Chem – volume: 8 start-page: 70 year: 2002 end-page: 89 ident: b0010 publication-title: CNS Drug Rev – volume: 102 start-page: 288 year: 2012 end-page: 297 ident: b0055 publication-title: Curr Sci – volume: 11 start-page: 1597 year: 2011 end-page: 1601 ident: b0065 publication-title: Synlett – volume: 111 start-page: 6557 year: 2011 end-page: 6602 ident: b0035 publication-title: Chem Rev – volume: 134 start-page: 17605 year: 2012 end-page: 17612 ident: b0050 publication-title: J Am Chem Soc – reference: Vorhis F, VJACKS Nootropics, Inc., Univ. Calif. Berkeley, 1999, 216, 371–4386. – volume: 42 start-page: 3929 year: 2016 end-page: 3977 ident: b0070 publication-title: Res Chem Intermed – volume: 14 start-page: 4646 year: 2012 end-page: 4649 ident: b0045 publication-title: Org Lett – volume: 9 start-page: 411 year: 2007 end-page: 420 ident: b0030 publication-title: Green Chem – reference: Willey AD, Miller LE, US Pat 5510477, 1996. – volume: 16 start-page: 288 year: 1968 end-page: 289 ident: b0075 publication-title: J Less-Common Met – volume: 43 start-page: 2714 year: 2014 end-page: 2742 ident: b0040 publication-title: Chem Soc Rev – reference: Kott KL, Willey AD, Miracle GS, Burckett-St.Laurent JC, WO Pat 1996016156A1, 1996. – volume: 14 start-page: 4646 year: 2012 ident: 10.1016/j.tetlet.2018.03.047_b0045 publication-title: Org Lett doi: 10.1021/ol302087z – volume: 8 start-page: 70 year: 2002 ident: 10.1016/j.tetlet.2018.03.047_b0010 publication-title: CNS Drug Rev doi: 10.1111/j.1527-3458.2002.tb00216.x – volume: 55 start-page: 9436 year: 2007 ident: 10.1016/j.tetlet.2018.03.047_b0015 publication-title: J Agric Food Chem doi: 10.1021/jf071963l – volume: 43 start-page: 2714 year: 2014 ident: 10.1016/j.tetlet.2018.03.047_b0040 publication-title: Chem Soc Rev doi: 10.1039/C3CS60345H – volume: 11 start-page: 1597 year: 2011 ident: 10.1016/j.tetlet.2018.03.047_b0065 publication-title: Synlett – volume: 111 start-page: 6557 year: 2011 ident: 10.1016/j.tetlet.2018.03.047_b0035 publication-title: Chem Rev doi: 10.1021/cr100048w – ident: 10.1016/j.tetlet.2018.03.047_b0085 – volume: 35 start-page: 6133 year: 1994 ident: 10.1016/j.tetlet.2018.03.047_b0060 publication-title: Tetrahedron Lett doi: 10.1016/0040-4039(94)88096-4 – volume: 9 start-page: 411 year: 2007 ident: 10.1016/j.tetlet.2018.03.047_b0030 publication-title: Green Chem doi: 10.1039/B703488C – volume: 37 start-page: 911 year: 1973 ident: 10.1016/j.tetlet.2018.03.047_b0005 publication-title: Agric Biol Chem doi: 10.1080/00021369.1973.10860743 – ident: 10.1016/j.tetlet.2018.03.047_b0025 – volume: 16 start-page: 288 year: 1968 ident: 10.1016/j.tetlet.2018.03.047_b0075 publication-title: J Less-Common Met doi: 10.1016/0022-5088(68)90026-X – ident: 10.1016/j.tetlet.2018.03.047_b0020 – volume: 70 start-page: 287 year: 2010 ident: 10.1016/j.tetlet.2018.03.047_b0080 publication-title: Drugs doi: 10.2165/11319230-000000000-00000 – volume: 134 start-page: 17605 year: 2012 ident: 10.1016/j.tetlet.2018.03.047_b0050 publication-title: J Am Chem Soc doi: 10.1021/ja306766n – volume: 102 start-page: 288 year: 2012 ident: 10.1016/j.tetlet.2018.03.047_b0055 publication-title: Curr Sci – volume: 42 start-page: 3929 year: 2016 ident: 10.1016/j.tetlet.2018.03.047_b0070 publication-title: Res Chem Intermed doi: 10.1007/s11164-015-2260-6 – volume: 55 start-page: 9436 year: 2007 ident: WOS:000250794100017 article-title: Isolation and identification of antiplatelet aggregatory principles from the leaves of Piper lolot publication-title: JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY doi: 10.1021/jf071963l – volume: 42 start-page: 3929 year: 2016 ident: WOS:000373617700001 article-title: A review on green Lewis acids: zirconium(IV) oxydichloride octahydrate (ZrOCl2 center dot 8H(2)O) and zirconium(IV) tetrachloride (ZrCl4) in organic chemistry publication-title: RESEARCH ON CHEMICAL INTERMEDIATES doi: 10.1007/s11164-015-2260-6 – start-page: 1597 year: 2011 ident: WOS:000291789200022 article-title: Zirconyl Chloride: An Efficient, Water-Tolerant, and Reusable Catalyst for the Synthesis of N-Methylamides publication-title: SYNLETT doi: 10.1055/s-0030-1260796 – volume: 16 start-page: 288 year: 1968 ident: WOS:A1968C087600012 article-title: ADDITION COMPOUNDS OF ZIRCONYL(4) CHLORIDE publication-title: JOURNAL OF THE LESS-COMMON METALS – volume: 43 start-page: 2714 year: 2014 ident: WOS:000333330200017 article-title: Catalytic amide formation from non-activated carboxylic acids and amines publication-title: CHEMICAL SOCIETY REVIEWS doi: 10.1039/c3cs60345h – year: 1996 ident: 000430524700010.1 publication-title: WO Pat – volume: 70 start-page: 287 year: 2010 ident: WOS:000275827700004 article-title: Piracetam and Piracetam-Like Drugs From Basic Science to Novel Clinical Applications to CNS Disorders publication-title: DRUGS – volume: 8 start-page: 70 year: 2002 ident: WOS:000176291100004 article-title: Aniracetam: Its novel therapeutic potential in cerebral dysfunctional disorders based on recent pharmacological discoveries publication-title: CNS DRUG REVIEWS – volume: 14 start-page: 4646 year: 2012 ident: WOS:000308390000090 article-title: Direct N-Acylation of Lactams, Oxazolidinones, and Imidazolidinones with Aldehydes by Shvo's Catalyst publication-title: ORGANIC LETTERS doi: 10.1021/ol302087z – volume: 134 start-page: 17605 year: 2012 ident: WOS:000310103800057 article-title: Catalytic, Enantioselective N-Acylation of Lactams and Thiolactams Using Amidine-Based Catalysts publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja306766n – volume: 37 start-page: 911 year: 1973 ident: WOS:A1973P691200028 article-title: SYNTHETIC STUDIES ON VARIOTINS .3. TOTAL SYNTHESIS OF DL-VARIOTIN publication-title: AGRICULTURAL AND BIOLOGICAL CHEMISTRY – volume: 102 start-page: 288 year: 2012 ident: WOS:000299857300022 article-title: Pyroglutamic acid: throwing light on a lightly studied metabolite publication-title: CURRENT SCIENCE – volume: 111 start-page: 6557 year: 2011 ident: WOS:000296685200002 article-title: Peptide Coupling Reagents, More than a Letter Soup publication-title: CHEMICAL REVIEWS doi: 10.1021/cr100048w – volume: 9 start-page: 411 year: 2007 ident: WOS:000246802600012 article-title: Key green chemistry research areas - a perspective from pharmaceutical manufacturers publication-title: GREEN CHEMISTRY doi: 10.1039/b703488c – year: 1996 ident: 000430524700010.2 publication-title: US Pat – volume: 35 start-page: 6133 year: 1994 ident: WOS:A1994PC53300046 article-title: FACILE ACID-CATALYZED RING-CLEAVAGE OF N-ACYLATED LACTAMS publication-title: TETRAHEDRON LETTERS |
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•New method for the catalytic N-acylation of lactams with carboxylic acids.•Screening of Lewis acid catalysts for N-acylation of pyroglutamic... A large number of chemicals including surfactants, nootropic drugs and pesticides contain an N-acylated lactam moiety in their molecular structure. In this... |
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| SubjectTerms | Aniracetam Catalysis catalysts chemical reactions Chemistry Chemistry, Organic drugs Lactam lactams Lewis acids moieties N-Acylation palmitic acid pesticides Physical Sciences Science & Technology surfactants temperature zirconium Zirconyl chloride |
| Title | Zirconium-catalysed N-acylation of lactams using unactivated carboxylic acids |
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