Convenient amidation of carboxyl group of carboxyphenylboronic acids
-
Julia Nowak-Jary
The use of catalysts in the activation of carboxyl groups towards nucleophilic attack and the protection of other functional groups by suitable protecting groups are standard and necessary procedures in amide bond formation. In contrast to the usual methods, various new compounds, amides of APTES ((3-aminopropyl)triethoxysilane, 3-triethoxysilylpropylamine) and carboxyphenylboronic acids, as well as the amides of aniline and carboxyphenylboronic acids, were obtained in good yields by a one-step synthesis under mild conditions without using any coupling reagents or additional catalysts.
References
Al-Zoubi, R. M., Marion, O., & Hall, D. G. (2008). Direct and waste-free amidations and cycloadditions by organocatalytic activation of carboxylic acids at room temperature. Angewandte Chemie International Edition, 47, 2876–2879. DOI: 10.1002/anie.200705468.10.1002/anie.200705468Suche in Google Scholar PubMed
Anderson, G. W., Zimmerman, J. E., & Callahan, F. M. (1964). The use of esters of N-hydroxysuccinimide in peptide synthesis. Journal of the American Chemical Society, 86, 1839–1842. DOI: 10.1021/ja01063a037.10.1021/ja01063a037Suche in Google Scholar
Gu, L., Lim, J., Cheong, J. L., & Lee, S. S. (2014). MCF-supported boronic acids as efficient catalysts for direct amide condensation of carboxylic acids and amines. Chemical Communications, 50, 7017–7019. DOI: 10.1039/c4cc01148a.10.1039/c4cc01148aSuche in Google Scholar PubMed
Jursic, B. S., & Zdravkovski, Z. (1993). A simple preparation of amides from acids by heating of their mixture. Synthetic Communications, 23, 2761–2770. DOI: 10.1080/00397919308013807.10.1080/00397919308013807Suche in Google Scholar
Lanigan, R. M., Starkov, P., & Sheppard, T. D. (2013). Direct synthesis of amides from carboxylic acids and amines using B(OCH2CF3)3. The Journal of Organic Chemistry, 78, 4512–4523. DOI: 10.1021/jo400509n.10.1021/jo400509nSuche in Google Scholar PubMed PubMed Central
Lundberg, H., Tinnis, F., Selander, N., & Adolfsson, H. (2014). Catalytic amide formation from non-activated carboxylic acids and amines. Chemical Society Reviews, 43, 2714–2742. DOI: 10.1039/c3cs60345h.10.1039/c3cs60345hSuche in Google Scholar PubMed
Montalbetti, C. A. G. N., & Falque, V. (2005). Amide bond formation and peptide coupling. Tetrahedron, 61, 10827–10852. DOI: 10.1016/j.tet.2005.08.031.10.1016/j.tet.2005.08.031Suche in Google Scholar
Mylavarapu, R. K., Kondaiah, G. C. M., Kolla, N., Veeramalla, R., Koilkonda, P., Bhattacharya, A., & Bandichhor, R. (2007). Boric acid catalyzed amidation in the synthesis of active pharmaceutical ingredients. Organic Process Research & Development, 11, 1065–1068. DOI: 10.1021/op700098w.10.1021/op700098wSuche in Google Scholar
Noda, H., & Bode, J. W. (2014). Synthesis and chemoselective ligations of MIDA acyloboronates with O-Me hydroxylamines. Chemical Science, 5, 4328–4332. DOI: 10.1039/c4sc00971a.10.1039/c4sc00971aSuche in Google Scholar
Sheehan, J., Cruickshank, P., & Boshart, G. (1961). A convenient synthesis of water-soluble carbodiimides. The Journal of Organic Chemistry, 26, 2525–2528. DOI: 10.1021/jo01351a600.10.1021/jo01351a600Suche in Google Scholar
Tam, E. K. W., Rita, Liu, L. Y., & Chen, A. (2015). 2-Furanylboronic acid as an effective catalyst for the direct amidation of carboxylic acids at room temperature. European Journal of Organic Chemistry, 2015, 1100–1107. DOI: 10.1002/ejoc.201403468.10.1002/ejoc.201403468Suche in Google Scholar
© 2015 Institute of Chemistry, Slovak Academy of Sciences
Artikel in diesem Heft
- Original Paper
- Preparation and characterisation of gelatine hydrogels predisposed to use as matrices for effective immobilisation of biocatalystst‡
- Original Paper
- Photocatalytic reduction of nitro aromatic compounds to amines using a nanosized highly active CdS photocatalyst under sunlight and blue LED irradiation
- Original Paper
- Synthesis of butyrate using a heterogeneous catalyst based on polyvinylpolypyrrolidone
- Original Paper
- Behaviour of selected pesticide residues in blackcurrants (Ribes nigrum) during technological processing monitored by liquid-chromatography tandem mass spectrometry
- Original Paper
- Influence of solvents and novel extraction methods on bioactive compounds and antioxidant capacity of Phyllanthus amarus
- Original Paper
- Investigation of phytochemicals and antioxidant capacity of selected Eucalyptus species using conventional extraction
- Original Paper
- Innovative approach to treating waste waters by a membrane capacitive deionisation system
- Original Paper
- Liquid—liquid equilibria of ternary systems of 1-hexene/hexane and extraction solvents
- Original Paper
- Design of extractive distillation process with mixed entraineri‡
- Original Paper
- Kinetic study of non-reactive iron removal from iron-gall inks
- Original Paper
- Chemoenzymatic polycondensation of para-benzylamino phenol
- Original Paper
- Copper corrosion behaviour in acidic sulphate media in the presence of 5-methyl-lH-benzotriazole and 5-chloro-lH-benzotriazole
- Original Paper
- Synthesis of new 5-bromo derivatives of indole and spiroindole phytoalexins
- Original Paper
- Design, synthesis and anti-mycobacterial evaluation of some new iV-phenylpyrazine-2-carboxamides
- Short Communication
- Convenient amidation of carboxyl group of carboxyphenylboronic acids
- Short Communication
- A novel intramolecular reversible reaction between the hydroxyl group and isobutenylene chain in a cyclophane-type macrocycle
- Erratum
- Erratum to “Adriana Bakalova, Boryana Nikolova-Mladenova, Rossen Buyukliev, Emiliya Cherneva, Georgi Momekov, Darvin Ivanov: Synthesis, DFT calculations and characterisation of new mixed Pt(II) complexes with 3-thiolanespiro-5′-hydantoin and 4-thio-1H-tetrahydropyranspiro-5′-hydantoin”, Chemical Papers 70 (1) 93–100 (2016)*
- Erratum
- Erratum to “Martyna Rzelewska, Monika Baczyńska, Magdalena Regel-Rosocka, Maciej Wiśniewski: Trihexyl(tetradecyl)phosphonium bromide as extractant for Rh(III), Ru(III) and Pt(IV) from chloride solutions”, Chemical Papers 70 (4) 454–460 (2016)*
Artikel in diesem Heft
- Original Paper
- Preparation and characterisation of gelatine hydrogels predisposed to use as matrices for effective immobilisation of biocatalystst‡
- Original Paper
- Photocatalytic reduction of nitro aromatic compounds to amines using a nanosized highly active CdS photocatalyst under sunlight and blue LED irradiation
- Original Paper
- Synthesis of butyrate using a heterogeneous catalyst based on polyvinylpolypyrrolidone
- Original Paper
- Behaviour of selected pesticide residues in blackcurrants (Ribes nigrum) during technological processing monitored by liquid-chromatography tandem mass spectrometry
- Original Paper
- Influence of solvents and novel extraction methods on bioactive compounds and antioxidant capacity of Phyllanthus amarus
- Original Paper
- Investigation of phytochemicals and antioxidant capacity of selected Eucalyptus species using conventional extraction
- Original Paper
- Innovative approach to treating waste waters by a membrane capacitive deionisation system
- Original Paper
- Liquid—liquid equilibria of ternary systems of 1-hexene/hexane and extraction solvents
- Original Paper
- Design of extractive distillation process with mixed entraineri‡
- Original Paper
- Kinetic study of non-reactive iron removal from iron-gall inks
- Original Paper
- Chemoenzymatic polycondensation of para-benzylamino phenol
- Original Paper
- Copper corrosion behaviour in acidic sulphate media in the presence of 5-methyl-lH-benzotriazole and 5-chloro-lH-benzotriazole
- Original Paper
- Synthesis of new 5-bromo derivatives of indole and spiroindole phytoalexins
- Original Paper
- Design, synthesis and anti-mycobacterial evaluation of some new iV-phenylpyrazine-2-carboxamides
- Short Communication
- Convenient amidation of carboxyl group of carboxyphenylboronic acids
- Short Communication
- A novel intramolecular reversible reaction between the hydroxyl group and isobutenylene chain in a cyclophane-type macrocycle
- Erratum
- Erratum to “Adriana Bakalova, Boryana Nikolova-Mladenova, Rossen Buyukliev, Emiliya Cherneva, Georgi Momekov, Darvin Ivanov: Synthesis, DFT calculations and characterisation of new mixed Pt(II) complexes with 3-thiolanespiro-5′-hydantoin and 4-thio-1H-tetrahydropyranspiro-5′-hydantoin”, Chemical Papers 70 (1) 93–100 (2016)*
- Erratum
- Erratum to “Martyna Rzelewska, Monika Baczyńska, Magdalena Regel-Rosocka, Maciej Wiśniewski: Trihexyl(tetradecyl)phosphonium bromide as extractant for Rh(III), Ru(III) and Pt(IV) from chloride solutions”, Chemical Papers 70 (4) 454–460 (2016)*
