Method of synthesis of 4-substituted 3-nitrophenyl carbonyls from benzyl alcohols

Daniil A. Kazantsev; Казанцев Д. А.; Alexander A. Denisov; Денисов А. А.; Alexander V. Pestov; Пестов А. В.

doi:10.31857/S0514749224120047

Method of synthesis of 4-substituted 3-nitrophenyl carbonyls from benzyl alcohols

Autores: Kazantsev D.A.¹, Denisov A.A.¹^,2, Pestov A.V.¹^,2
Afiliações:
1. I.Ya. Postovsky Insititute of Organic Synthesis of the Ural Branch of the Russian Academy of Sciences
2. Ural Federal University
Edição: Volume 60, Nº 12 (2024)
Páginas: 1209-1215
Seção: Articles
URL: https://rjeid.com/0514-7492/article/view/681813
DOI: https://doi.org/10.31857/S0514749224120047
EDN: https://elibrary.ru/AQMXWT
ID: 681813

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Resumo

A method has been developed for the production of 4-substituted-3-nitrophenyl carbonyl s based on the tandem oxidation and nitration process of benzyl alcohols. The proposed method is single-reactor and makes it possible to obtain target compounds with good yield, under mild conditions, using stable commercially available starting substances.

Palavras-chave

nitrooxidation, tandem process, 4-chloro-3-nitrobenzaldehyde, 4-bromo-3-nitrobenzaldehyde, 4-methyl-3-nitrobenzaldehyde, (4-methyl-3-nitrophenyl)phenylketon

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Sobre autores

Daniil Kazantsev

I.Ya. Postovsky Insititute of Organic Synthesis of the Ural Branch of the Russian Academy of Sciences

Autor responsável pela correspondência
Email: daniil_kazantsev@mail.ru
ORCID ID: 0009-0008-8648-3395
Rússia, Sofya Kovalevskaya st., 22/20, Yekaterinburg, 620108

Alexander Denisov

I.Ya. Postovsky Insititute of Organic Synthesis of the Ural Branch of the Russian Academy of Sciences; Ural Federal University

Email: daniil_kazantsev@mail.ru
ORCID ID: 0009-0000-4715-8284

Ural Federal University, The Institute of Natural Sciences and Mathematics

Rússia, Sofya Kovalevskaya st., 22/20, Yekaterinburg, 620108; Kuibysheva st., 48, Yekaterinburg, 620026

Alexander Pestov

I.Ya. Postovsky Insititute of Organic Synthesis of the Ural Branch of the Russian Academy of Sciences; Ural Federal University

Email: daniil_kazantsev@mail.ru
ORCID ID: 0000-0002-4270-3041

Ural Federal University, The Institute of Natural Sciences and Mathematics

Rússia, Sofya Kovalevskaya st., 22/20, Yekaterinburg, 620108; Kuibysheva st., 48, Yekaterinburg, 620026

Bibliografia

Pease A.C., Solas D., Sullivan E.J., Cronin M.T., Holmes C.P., Fodor S.P. Biochemistry. 1994, 91 (11), 5022–5026. doi: 10.1073/pnas.91.11.5022
Kretcchy N., Holik A.-K., Somoza V., Stengele K.-P., Somoza M. M. Angew. Chem. Int. Ed. 2015, 54 (29), 8555–8559.
Stengele K.-P. Международная заявка. WO 2012/136604. C.A. 2012, 136604 A1.
Klan P., Solomek T., Bochet C.G., Blank A., Givens R., Rubina M., Popik V., Kostikov A., Wirz J. Chem. Rev. 2013, 113, 119–191. doi: 10.1021/cr300177k
Grigor'ev E.I., Zhil'tsov O.S. Russ. J. Org. Chem., 1989, 25 (9), 1963–1967.
Chandrappa S., Sadashiva M. P., Rangappa K.S. Synth. Commun. 2008, 38 (15), 2638–2645. doi: 10.1080/00397910802219502
Somey M. Chem. Pharm. Bull., 1986, 34 (10), 4109–4115. doi: 10.1248/cpb.34.4109
Saaidin A.S., Murai Y., Ishikawa T., Monde K. Eur. J. Org. Chem. 2019, 46, 7563–7567. doi: 10.1002/eJoc.201901348
Flitsch W., Russkamp P., Langer W. Liebigs Ann. Chem., 1985, 7, 1413–1421. doi: 10.1002/chin.198546320
Swoboda P., Saf R., Hummel K., Hofer F., Czaputa R. Macromolecules. 1995, 28 (12), 4255–4259. doi: 10.1021/ma00116a028
Bykov V.V., Korolev D.N., Bumagin N.A. Russ. Chem. Bull. 1997, 46, 1631–1632. doi: 10.1007/BF02502959
Strazzolini P., Runcio A. Eur. J. Org. Chem. 2003, 3, 526–536. doi: 10.1002/eJoc.200390090