Abstract
Catalysis of the acylation of aniline with 3-hydroxy-2-naphthoic, 1-hydroxy-2-naphthoic, 2-hydroxy-1-naphthoic and 1-hydroxy-4-naphthoic acids by phosphorus P(III) and silicon Si(IV) compounds leads to the formation anilides of the corresponding hydroxynaphthoic acids under mild conditions (ortho-xylene, 146.5–147 °C) in almost quantitative yield.
Among P(III) phosphorus trichloride and tribromide; phosphorous, 1-hydroxyethylidene-diphosphonic, pyrophosphorous and metaphosphorous acids; trimethyl-, dimethyl- and diethylphosphites; phosph(III)azan proved to be active catalysts; among Si(IV) – trichloro-(methyl)silane, dichloro(ethyl)silane, dichloro(dimethyl)silane, tetrachlorosilane and tetraethoxysilane are active.
The catalysts were used in an amount of only 2% mole. from hydroxynaphthoic acid, which is 15–35 times less than the conventional use of the same compounds as condensing agents in the synthesis of carboxylic acid arylamides. P(V) compounds, thionyl chloride, and sulfuryl chloride practically do not exhibit catalytic activity. The presence of catalytic activity only in P(III) compounds, capable of forming phosphorous acid in the reaction mass, does not contradict to the previously proposed mechanism of P = O-nucleophilic catalysis for the reaction of substituted benzoic acids with aniline catalyzed by PCl3.
In general, the use of P(III) and Si(IV) compounds as catalysts in the preparation of hydroxybenzoic and hydroxynaphthoic acid anilides successfully complements the range of catalysts, based on Ti(IV) compounds, previously used in the formation of substituted benzoic and naphthoic acid anilides (containing no aromatically bonded hydroxy group), allowing to create a universal method for their synthesis.
References
Vorozhtsov N.N. Fundamentals of the synthesis of intermediates and dyes. (M.: Goshimizdat, 1955) [in Russian].
Gonec T., Kos J., Zadrazilova I., Pesko M., Govender R., Keltosova S., Chambel B., Pereira D., Kollar P., Imramovsky A., O’Mahony J., Coffey A., Cizek A., Kralova K., Jampilek J. Antibacterial and herbicidal activity of ring-substituted 2-hydroxynaphthalene-1-carboxanilides. Molecules. 2013. 18: 9397.
Michalik M., Poliak P., Lukes V. B3LYP Study of 3-hydroxynaphthalene-2-carboxanilide para-derivatives. Acta Chim. Slov. 2018. 65: 23.
Gonec T., Kos J., Pesko M., Dohanosova J., Oravec M., Liptaj T., Kralova K., Jampilek J. Halogenated 1-hydroxynaphthalene-2-сarboxani-lides affecting photosynthetic electron transport in photosystem II. Molecules. 2017. 22(10): 1709.
Guben I. Methods of organic chemistry. Moscow: ONTI-Main edition of chemical literature, 1935. 3(2) [in Russian].
CN104447392A (2016).
CN106316874A (2017).
CN1128134C (2003).
Shteinberg L.Ya. Catalytic method for the synthesis of 3-hydroxy-2-naphthoic acid anilide. Ukr. khim. zhurn. 2022. 88(10): 77.
Sharma P.K., Mathur D., Malhotra S., Rana N., Singh B.K., Prasad A.K., Varma A.J., Shakil N.A., Ghosh B., Len C., Kuhad R.C., Jerome F., Parmar V.S. Triphenyl рhosphite-mediated «green» synthesis of novel carboxycoumarin amides. Current Green Chemistry. 2016. 3(4): 366.
Shteinberg L.Ya. Catalysis of the reaction of substituted benzoic acids with aniline by compounds of trivalent phosphorus. Ukr. khim. zhurn. 2022. 88 (6): 119.
Shteinberg L.Ya., Boyko V.D., Kondratov S.A., Shein S.M., Shteinberg Ya.B. Catalysis with phosphorus compounds in the reaction of benzoic acid with aniline. Zhurn. organ. khimii. 1992. 28(5): 1034.
C.А. 477941(1975).
Shteinberg L.Ya., Dibrova V.M., Shein S.M. Phosphorous acid catalysis in the synthesis of benzanilide. Ukr. khim. zhurn. 2012. 78(2): 119.
Donaldson N. Chemistry and technology of compounds of the naphthalene series. Moscow: GONTI HL, 1963 [in Russian].
Katsarava R.D. Condensing agents in polycondensation. Uspechi khimii. 1989. 58(9): 1549.
Luo Q.-L., Lv L., Li Y., Tan J.-P., Nan W., Hui Q. An Efficient protocol for the amidation of carboxylic acids promoted by trimethylphosphite and iodine. Eur. J. Org. Chem. 2011. 34: 6916.
Wade Jr.L.G. Organic Chemistry. 6th ed., Р. 1051, Pearson/Prentice Hall, Upper Saddle River, New Jersey, USA, 2005.
US Patent 3200150 (1965).
Savant M.M., Pansuriya A.M., Bhuva C.V., Kapuriya N.P., Naliapara Y.T. Etidronic аcid: a new and efficient catalyst for the synthesis of novel 5-nitro-3,4-dihydropyrimidin-2(1H)-ones. Catal. Lett. 2009. 132(1): 281.
Zhen Yang, Siwei Chen, Chenxi Zhang, You Dou, Qiuju Zhou, Yizhe Yan, Lin Tang. PPh3/ selectfluor-mediated transformation of carboxylic acids into acid anhydrides and acyl fluorides and its application in amide and ester synthesis. Eur. J. Organ. Chem. 2019. 2019(34): 5998.
Corbridge D. Phosphorus: Fundamentals of Chemistry, Biochemistry, Technology. M.: Mir, 1982 [in Russian].
Nitta I., Watanabe T., Taguchi I. The Crystal structure of orthorhombic aniline hydrobromide. Bulletin of chemical society of Japan. 1961. 34(10): 1405.
https://theses.gla.ac.uk/79430/1/13849308.pdf A Srudy of phosphites. A Thesis presented to the University of Glasgow in part fulfillment of the requirements for the degree of doctor of philosophy.1962.
Van Veser. Phosphorus and its compounds. M.: INLIT, 1962 [in Russian].
Joullie M.M., Lassen K.M. Evolution of amide bond formation ARKIVOC. 2010. (8): 189.
Ghosh M.K., Mittal K.L. Polyimides: Fundamentals and Applications. New-York – Basel: Marcel Dekker, Inc. 1996.
Valeur Е., Bradley М. Amide bond formation: beyond the myth of coupling reagents. Chem. Soc. Rev. 2009. 38: 606.
Vapirov V.V. Reactivity of hexachlorocyclotriphospazotriene in nucleophilic substitution reactions. Diss. doct. chem. sciences. St. Petersburg. 2000.
Pulle J.S. Synthesis of amides by activation of carboxylic acids using phosphonitrilic chloride. Indo American Journal of Pharmaceutical Research. 2020. 10(1): 599.
Albert A., Sergeant E. Ionization constants for acids and bases. M. – L.: Khimiya, 1964 [in Russian].
Hudson R. Structure and mechanism of reactions of organophosphorus compounds. M.: Mir, 1967 [in Russian].
Dyatlova N.M., Temkina V.Ya., Popov K.I. Metal complexons and complexonates. M: Khimiya, 1988 [in Russian].
Savelova V.A., Oleinik N.M. Mechanisms of action of organic catalysts. Bifunctional and intramolecular catalysis. Kyiv: Naukova Dumka, 1990 [in Russian].
Kaslina N.A., Krinitskaya L.V., Kessenikh A.V., Balashova T.M., Reshetnikov Yu.P., Skalatsky E.V. Investigation of the hydrolysis of dimethyl phosphite by NMR spectroscopy. Chemical reagents and extra pure substances. Scientific works. M. 1989. (51): 56.
Kopylov V.A. Technology of extraction phosphoric acid. L.: Khimiya, 1972 [in Russian].
US Patent 3253036 (1966).
Silicon compounds: silanes and silicones. A Survey of properties and chemistry. 3rd Edition. Edited by Arkles B. and Larson G.L. 2013. Copyright by Gelest, Inc., Morrisville, PA.1608. <https://www.researchgate.net/publication/ 27 3439829_Silicon_Compounds_Silanes_Silicones>
Wong L.T. L.Part 1. Silicon tetrachloride as a coupling reagent for amide bond formation. A thesis submitted in conformity with the requirements for the degree of Doctor of Philosophy. McGill University. 1971. https://escholarship.mcgill.ca › downloads
Braddock D.С., Lickiss P. D., Rowley B.C, Pugh D., Purnomo T., Santhakumar G., Fussel S.J. Tetramethyl orthosilicate (TMOS) as a reagent for direct amidation of carboxylic acids. Org. Lett. 2018. 20: 950.