Synthesis and Structural Analysis of Chiral Bis-dihydro[1,3]-naphthoxazines and Imidazolidine Derivatives Prepared by Three-Component Mannich-Type Condensation
Enantiomerically pure (<i>S</i>)-1-phenylethan-1-amine has been applied in Mannich-type condensation between formaldehyde and naphthalenediols leading to the synthesis of chiral bis-dihydro[1,3]naphthoxazines in excellent yields. Salen-type structures have been synthesized, applying <...
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MDPI AG
2023-10-01
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| author | Maya Tavlinova-Kirilova Krasimira Dikova Maya K. Marinova Mariana Kamenova-Nacheva Rusi Rusew Hristina Sbirkova-Dimitrova Boris Shivachev Kalina Kostova Vladimir Dimitrov |
| author_facet | Maya Tavlinova-Kirilova Krasimira Dikova Maya K. Marinova Mariana Kamenova-Nacheva Rusi Rusew Hristina Sbirkova-Dimitrova Boris Shivachev Kalina Kostova Vladimir Dimitrov |
| author_sort | Maya Tavlinova-Kirilova |
| collection | DOAJ |
| description | Enantiomerically pure (<i>S</i>)-1-phenylethan-1-amine has been applied in Mannich-type condensation between formaldehyde and naphthalenediols leading to the synthesis of chiral bis-dihydro[1,3]naphthoxazines in excellent yields. Salen-type structures have been synthesized, applying <i>R</i>,<i>R</i>- or <i>S</i>,<i>S</i>-cyclohexane-1,2-diamines in condensation with formaldehyde and naphthalene-2-ol. The obtained chiral imidazolidine derivatives of the type 1,1′-(((3a,7a)-hexahydro-1<i>H</i>-benzo[<i>d</i>]imidazole-1,3(2<i>H</i>)diyl)bis(methylene))bis(naphthalen-2-ol) were evaluated as pre-catalysts for the addition of diethyl zinc to aldehydes. The structures of the newly synthesized compounds were elucidated using <sup>1</sup>D and <sup>2</sup>D NMR experiments (COSY, HMBC, HSQS), elemental analysis, mass spectrometry (HRMS spectra) and single-crystal X-ray diffraction (SCXRD). The products were further characterized with powder X-ray diffraction (PXRD) and thermal analysis (DSC). |
| first_indexed | 2024-03-10T21:19:51Z |
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| issn | 2073-4352 |
| language | English |
| last_indexed | 2024-03-10T21:19:51Z |
| publishDate | 2023-10-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Crystals |
| spelling | doaj.art-922dadd8b9ce4177a75f21d58d08d3e52023-11-19T16:10:03ZengMDPI AGCrystals2073-43522023-10-011310149510.3390/cryst13101495Synthesis and Structural Analysis of Chiral Bis-dihydro[1,3]-naphthoxazines and Imidazolidine Derivatives Prepared by Three-Component Mannich-Type CondensationMaya Tavlinova-Kirilova0Krasimira Dikova1Maya K. Marinova2Mariana Kamenova-Nacheva3Rusi Rusew4Hristina Sbirkova-Dimitrova5Boris Shivachev6Kalina Kostova7Vladimir Dimitrov8Institute of Organic Chemistry with Centre of Phytochemistry, Bulgarian Academy of Sciences, Acad. G. Bonchev Street, bl. 9, 1113 Sofia, BulgariaInstitute of Organic Chemistry with Centre of Phytochemistry, Bulgarian Academy of Sciences, Acad. G. Bonchev Street, bl. 9, 1113 Sofia, BulgariaInstitute of Organic Chemistry with Centre of Phytochemistry, Bulgarian Academy of Sciences, Acad. G. Bonchev Street, bl. 9, 1113 Sofia, BulgariaInstitute of Organic Chemistry with Centre of Phytochemistry, Bulgarian Academy of Sciences, Acad. G. Bonchev Street, bl. 9, 1113 Sofia, BulgariaInstitute of Mineralogy and Crystallography “Acad. Ivan Kostov”, Bulgarian Academy of Sciences, Acad. G. Bonchev Street, bl. 107, 1113 Sofia, BulgariaInstitute of Mineralogy and Crystallography “Acad. Ivan Kostov”, Bulgarian Academy of Sciences, Acad. G. Bonchev Street, bl. 107, 1113 Sofia, BulgariaInstitute of Mineralogy and Crystallography “Acad. Ivan Kostov”, Bulgarian Academy of Sciences, Acad. G. Bonchev Street, bl. 107, 1113 Sofia, BulgariaInstitute of Organic Chemistry with Centre of Phytochemistry, Bulgarian Academy of Sciences, Acad. G. Bonchev Street, bl. 9, 1113 Sofia, BulgariaInstitute of Organic Chemistry with Centre of Phytochemistry, Bulgarian Academy of Sciences, Acad. G. Bonchev Street, bl. 9, 1113 Sofia, BulgariaEnantiomerically pure (<i>S</i>)-1-phenylethan-1-amine has been applied in Mannich-type condensation between formaldehyde and naphthalenediols leading to the synthesis of chiral bis-dihydro[1,3]naphthoxazines in excellent yields. Salen-type structures have been synthesized, applying <i>R</i>,<i>R</i>- or <i>S</i>,<i>S</i>-cyclohexane-1,2-diamines in condensation with formaldehyde and naphthalene-2-ol. The obtained chiral imidazolidine derivatives of the type 1,1′-(((3a,7a)-hexahydro-1<i>H</i>-benzo[<i>d</i>]imidazole-1,3(2<i>H</i>)diyl)bis(methylene))bis(naphthalen-2-ol) were evaluated as pre-catalysts for the addition of diethyl zinc to aldehydes. The structures of the newly synthesized compounds were elucidated using <sup>1</sup>D and <sup>2</sup>D NMR experiments (COSY, HMBC, HSQS), elemental analysis, mass spectrometry (HRMS spectra) and single-crystal X-ray diffraction (SCXRD). The products were further characterized with powder X-ray diffraction (PXRD) and thermal analysis (DSC).https://www.mdpi.com/2073-4352/13/10/1495Mannich condensationbis-dihydro[1,3]naphthoxazines<i>R</i>,<i>R</i>- or <i>S</i>,<i>S</i>-cyclohexane-1,2-diaminechiral ligandenantioselectivityX-ray crystallography |
| spellingShingle | Maya Tavlinova-Kirilova Krasimira Dikova Maya K. Marinova Mariana Kamenova-Nacheva Rusi Rusew Hristina Sbirkova-Dimitrova Boris Shivachev Kalina Kostova Vladimir Dimitrov Synthesis and Structural Analysis of Chiral Bis-dihydro[1,3]-naphthoxazines and Imidazolidine Derivatives Prepared by Three-Component Mannich-Type Condensation Crystals Mannich condensation bis-dihydro[1,3]naphthoxazines <i>R</i>,<i>R</i>- or <i>S</i>,<i>S</i>-cyclohexane-1,2-diamine chiral ligand enantioselectivity X-ray crystallography |
| title | Synthesis and Structural Analysis of Chiral Bis-dihydro[1,3]-naphthoxazines and Imidazolidine Derivatives Prepared by Three-Component Mannich-Type Condensation |
| title_full | Synthesis and Structural Analysis of Chiral Bis-dihydro[1,3]-naphthoxazines and Imidazolidine Derivatives Prepared by Three-Component Mannich-Type Condensation |
| title_fullStr | Synthesis and Structural Analysis of Chiral Bis-dihydro[1,3]-naphthoxazines and Imidazolidine Derivatives Prepared by Three-Component Mannich-Type Condensation |
| title_full_unstemmed | Synthesis and Structural Analysis of Chiral Bis-dihydro[1,3]-naphthoxazines and Imidazolidine Derivatives Prepared by Three-Component Mannich-Type Condensation |
| title_short | Synthesis and Structural Analysis of Chiral Bis-dihydro[1,3]-naphthoxazines and Imidazolidine Derivatives Prepared by Three-Component Mannich-Type Condensation |
| title_sort | synthesis and structural analysis of chiral bis dihydro 1 3 naphthoxazines and imidazolidine derivatives prepared by three component mannich type condensation |
| topic | Mannich condensation bis-dihydro[1,3]naphthoxazines <i>R</i>,<i>R</i>- or <i>S</i>,<i>S</i>-cyclohexane-1,2-diamine chiral ligand enantioselectivity X-ray crystallography |
| url | https://www.mdpi.com/2073-4352/13/10/1495 |
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