Functionalized <i>C</i><sub>3</sub>-Symmetric Building Blocks—The Chemistry of Triaminotrimesic Acid
A series of <i>C</i><sub>3</sub>-symmetric fully substituted benzenes were prepared based on alkyl triamino-benzene-tricarboxylates. Starting with a one step-synthesis, the alkyl triamino-benzene-tricarboxylates were synthesized using the corresponding cyanoacetates. The reac...
| Main Authors: | , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2022-07-01
|
| Series: | Molecules |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1420-3049/27/14/4369 |
| _version_ | 1797416770153218048 |
|---|---|
| author | Lisa Schmidt Danny Wagner Martin Nieger Stefan Bräse |
| author_facet | Lisa Schmidt Danny Wagner Martin Nieger Stefan Bräse |
| author_sort | Lisa Schmidt |
| collection | DOAJ |
| description | A series of <i>C</i><sub>3</sub>-symmetric fully substituted benzenes were prepared based on alkyl triamino-benzene-tricarboxylates. Starting with a one step-synthesis, the alkyl triamino-benzene-tricarboxylates were synthesized using the corresponding cyanoacetates. The reactivity of these electronically sophisticated compounds was investigated by the formation of azides, the click reaction of the azides and a <span style="font-variant: small-caps;">Sandmeyer</span>-like reaction. Caused by the low stability of triaminobenzenes, direct <i>N</i>-alkylation was rarely reported. The use of the stable alkyl triamino-benzene-tricarboxylates allowed us total <i>N</i>-alkylation under standard alkylation conditions. The molecular structures of the <i>C</i><sub>3</sub>-symmetric structures have been corroborated by an X-ray analysis. |
| first_indexed | 2024-03-09T06:07:52Z |
| format | Article |
| id | doaj.art-009ffd29fa0643f7837b7dfcebdc1713 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-09T06:07:52Z |
| publishDate | 2022-07-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-009ffd29fa0643f7837b7dfcebdc17132023-12-03T12:00:49ZengMDPI AGMolecules1420-30492022-07-012714436910.3390/molecules27144369Functionalized <i>C</i><sub>3</sub>-Symmetric Building Blocks—The Chemistry of Triaminotrimesic AcidLisa Schmidt0Danny Wagner1Martin Nieger2Stefan Bräse3Institute of Organic Chemistry, Karlsruhe Institute of Technology (KIT), Fritz-Haber-Weg 6, 76131 Karlsruhe, GermanyInstitute of Organic Chemistry, Karlsruhe Institute of Technology (KIT), Fritz-Haber-Weg 6, 76131 Karlsruhe, GermanyDepartment of Chemistry, University of Helsinki, P.O. Box 55 (A. I. Virtasen aukio 1), FIN-00014 Helsinki, FinlandInstitute of Organic Chemistry, Karlsruhe Institute of Technology (KIT), Fritz-Haber-Weg 6, 76131 Karlsruhe, GermanyA series of <i>C</i><sub>3</sub>-symmetric fully substituted benzenes were prepared based on alkyl triamino-benzene-tricarboxylates. Starting with a one step-synthesis, the alkyl triamino-benzene-tricarboxylates were synthesized using the corresponding cyanoacetates. The reactivity of these electronically sophisticated compounds was investigated by the formation of azides, the click reaction of the azides and a <span style="font-variant: small-caps;">Sandmeyer</span>-like reaction. Caused by the low stability of triaminobenzenes, direct <i>N</i>-alkylation was rarely reported. The use of the stable alkyl triamino-benzene-tricarboxylates allowed us total <i>N</i>-alkylation under standard alkylation conditions. The molecular structures of the <i>C</i><sub>3</sub>-symmetric structures have been corroborated by an X-ray analysis.https://www.mdpi.com/1420-3049/27/14/4369azidesclick reactions<i>C</i><sub>3</sub>-symmetrical building blockscarboxylic acidsX-ray |
| spellingShingle | Lisa Schmidt Danny Wagner Martin Nieger Stefan Bräse Functionalized <i>C</i><sub>3</sub>-Symmetric Building Blocks—The Chemistry of Triaminotrimesic Acid Molecules azides click reactions <i>C</i><sub>3</sub>-symmetrical building blocks carboxylic acids X-ray |
| title | Functionalized <i>C</i><sub>3</sub>-Symmetric Building Blocks—The Chemistry of Triaminotrimesic Acid |
| title_full | Functionalized <i>C</i><sub>3</sub>-Symmetric Building Blocks—The Chemistry of Triaminotrimesic Acid |
| title_fullStr | Functionalized <i>C</i><sub>3</sub>-Symmetric Building Blocks—The Chemistry of Triaminotrimesic Acid |
| title_full_unstemmed | Functionalized <i>C</i><sub>3</sub>-Symmetric Building Blocks—The Chemistry of Triaminotrimesic Acid |
| title_short | Functionalized <i>C</i><sub>3</sub>-Symmetric Building Blocks—The Chemistry of Triaminotrimesic Acid |
| title_sort | functionalized i c i sub 3 sub symmetric building blocks the chemistry of triaminotrimesic acid |
| topic | azides click reactions <i>C</i><sub>3</sub>-symmetrical building blocks carboxylic acids X-ray |
| url | https://www.mdpi.com/1420-3049/27/14/4369 |
| work_keys_str_mv | AT lisaschmidt functionalizedicisub3subsymmetricbuildingblocksthechemistryoftriaminotrimesicacid AT dannywagner functionalizedicisub3subsymmetricbuildingblocksthechemistryoftriaminotrimesicacid AT martinnieger functionalizedicisub3subsymmetricbuildingblocksthechemistryoftriaminotrimesicacid AT stefanbrase functionalizedicisub3subsymmetricbuildingblocksthechemistryoftriaminotrimesicacid |