Supramolecular aminocatalysis via inclusion complex: Amino-doped β-cyclodextrin as an efficient supramolecular catalyst for the synthesis of chromeno pyrimido[1,2-b]indazol in water
[Display omitted] •Amino-appended β-cyclodextrin (AA-β-CD) as a supramolecular organic base catalyst were synthesized.•AA-β-CD catalyzed the synthesis of chromeno pyrimido[1,2-b]indazol derivatives.•AA-β-CD as a catalyst can be easily recovered and reused.•Reaction mechanism was elucidated extensive...
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| Published in | Journal of industrial and engineering chemistry (Seoul, Korea) Vol. 68; pp. 6 - 13 |
|---|---|
| Main Authors | , , |
| Format | Journal Article |
| Language | English |
| Published |
Elsevier B.V
25.12.2018
한국공업화학회 |
| Subjects | |
| Online Access | Get full text |
| ISSN | 1226-086X 1876-794X |
| DOI | 10.1016/j.jiec.2018.08.010 |
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| Abstract | [Display omitted]
•Amino-appended β-cyclodextrin (AA-β-CD) as a supramolecular organic base catalyst were synthesized.•AA-β-CD catalyzed the synthesis of chromeno pyrimido[1,2-b]indazol derivatives.•AA-β-CD as a catalyst can be easily recovered and reused.•Reaction mechanism was elucidated extensively by spectroscopic analysis.
Well-modified amino-appended β-cyclodextrin (AA-β-CD) with an amino group at the primary face of the β-CD was synthesized and used in the catalytic synthesis of chromeno pyrimido[1,2-b]indazol as supramolecular catalysts in water for the first time. AA-β-CD was characterized by FT-IR, NMR, MALDI-TOF mass spectrometry, and SEM analysis. A possible reaction mechanism featuring molecular complexation was suggested based on 2D NMR (ROESY) spectroscopy, FE-SEM, DSC, and FT-IR. Advantages such as operational simplicity, recyclability of the catalysts, and accessibility in aqueous medium render this protocol eco-friendly. |
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| AbstractList | [Display omitted]
•Amino-appended β-cyclodextrin (AA-β-CD) as a supramolecular organic base catalyst were synthesized.•AA-β-CD catalyzed the synthesis of chromeno pyrimido[1,2-b]indazol derivatives.•AA-β-CD as a catalyst can be easily recovered and reused.•Reaction mechanism was elucidated extensively by spectroscopic analysis.
Well-modified amino-appended β-cyclodextrin (AA-β-CD) with an amino group at the primary face of the β-CD was synthesized and used in the catalytic synthesis of chromeno pyrimido[1,2-b]indazol as supramolecular catalysts in water for the first time. AA-β-CD was characterized by FT-IR, NMR, MALDI-TOF mass spectrometry, and SEM analysis. A possible reaction mechanism featuring molecular complexation was suggested based on 2D NMR (ROESY) spectroscopy, FE-SEM, DSC, and FT-IR. Advantages such as operational simplicity, recyclability of the catalysts, and accessibility in aqueous medium render this protocol eco-friendly. Well-modified amino-appended β-cyclodextrin (AA-β-CD) with an amino group at the primary face of the β-CD was synthesized and used in the catalytic synthesis of chromeno pyrimido[1,2-b]indazol as supramolecular catalysts in water for the first time. AA-β-CD was characterized by FT-IR, NMR, MALDI-TOF mass spectrometry, and SEM analysis. A possible reaction mechanism featuring molecular complexation was suggested based on 2D NMR (ROESY) spectroscopy, FE-SEM, DSC, and FT-IR. Advantages such as operational simplicity, recyclability of the catalysts, and accessibility in aqueous medium render this protocol eco-friendly. KCI Citation Count: 12 |
| Author | Jeong, Daham Jung, Seunho Shinde, Vijay Vilas |
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| CitedBy_id | crossref_primary_10_1016_j_tet_2018_12_059 crossref_primary_10_1007_s10853_020_04621_7 crossref_primary_10_1016_j_eurpolymj_2024_113178 crossref_primary_10_1002_ejoc_202101446 crossref_primary_10_3390_polym12020393 crossref_primary_10_1021_acs_orglett_8b02813 crossref_primary_10_1021_acs_joc_0c00420 crossref_primary_10_1021_acsomega_9b02755 crossref_primary_10_1007_s10853_021_06126_3 crossref_primary_10_1080_09205063_2021_1980358 crossref_primary_10_1016_j_colsurfb_2020_111311 crossref_primary_10_1016_j_ijbiomac_2019_05_197 crossref_primary_10_1007_s00216_020_02488_w crossref_primary_10_1016_j_jiec_2019_06_051 crossref_primary_10_2174_1385272826666220430145522 crossref_primary_10_1016_j_aca_2020_06_036 |
| Cites_doi | 10.15227/orgsyn.077.0225 10.1021/ja055735o 10.1021/sc3000866 10.1021/jm00385a012 10.1016/j.catcom.2017.10.001 10.1039/p19920001811 10.1016/j.ejpb.2003.10.019 10.1007/s11030-015-9579-1 10.1007/s00044-011-9631-3 10.1039/C3CS60037H 10.1016/j.ejmech.2007.03.031 10.1016/j.tet.2017.07.035 10.1016/j.addr.2013.05.001 10.1007/s00044-011-9962-0 10.1007/s11030-017-9746-7 10.1016/j.tet.2017.03.084 10.1021/jo01012a028 10.1021/jo501049m 10.1016/j.tet.2016.06.002 10.1016/j.ejmech.2006.03.028 10.1021/jo302173a 10.1002/jhet.5570100229 10.1002/anie.200803731 10.1002/cber.19721050308 10.1039/C5CY01888A 10.1016/j.tet.2005.02.046 10.1016/j.ejps.2007.09.010 10.1039/c3gc41799a 10.1016/S0040-4039(01)93353-2 10.1021/jo801811w |
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| Keywords | One-pot synthesis Mono-6-deoxy-6-amino-β-cyclodextrin Poly heterocycles Amino-appended supramolecular catalyst 2D ROESY NMR |
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•Amino-appended β-cyclodextrin (AA-β-CD) as a supramolecular organic base catalyst were synthesized.•AA-β-CD catalyzed the synthesis of... Well-modified amino-appended β-cyclodextrin (AA-β-CD) with an amino group at the primary face of the β-CD was synthesized and used in the catalytic synthesis... |
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| SubjectTerms | 2D ROESY NMR Amino-appended supramolecular catalyst Mono-6-deoxy-6-amino-β-cyclodextrin One-pot synthesis Poly heterocycles 화학공학 |
| Title | Supramolecular aminocatalysis via inclusion complex: Amino-doped β-cyclodextrin as an efficient supramolecular catalyst for the synthesis of chromeno pyrimido[1,2-b]indazol in water |
| URI | https://dx.doi.org/10.1016/j.jiec.2018.08.010 https://www.kci.go.kr/kciportal/ci/sereArticleSearch/ciSereArtiView.kci?sereArticleSearchBean.artiId=ART002414613 |
| Volume | 68 |
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| ispartofPNX | Journal of Industrial and Engineering Chemistry, 2018, 68(0), , pp.6-13 |
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