Keywords
acridine catalysis
azomethine imines
carboxylic acids
decatungstate
photocatalysis
pyrazolidin-3-ones.
radical reactions
Abstract
The alkylation of cyclic five-membered azomethine imines with carboxylic acids proceeds under irradiation with 400 nm light using a dual catalytic system consisting of 9-arylacridine and tetrabutylammonium decatungstate. Azomethine imines containing aromatic, heterocyclic and aliphatic groups are suitable for the process providing pyrazolidin-3-ones in 42-98% yields.
References
.
Cannalire R., Pelliccia S., Sancineto L., Novellino E., Tron G.C., Giustiniano M.
Chemical Society Reviews,
2021
.
Candish L., Collins K.D., Cook G.C., Douglas J.J., Gómez-Suárez A., Jolit A., Keess S.
Chemical Reviews,
2021
.
Iglesias J., Martínez-Salazar I., Maireles-Torres P., Martin Alonso D., Mariscal R., López Granados M.
Chemical Society Reviews,
2020
.
Zubkov M.O., Kosobokov M.D., Levin V.V., Dilman A.D.
Organic Letters,
2022
.
Romero N.A., Nicewicz D.A.
Chemical Reviews,
2016
.
Nájera C., Sansano J.M., Yus M.
Organic and Biomolecular Chemistry,
2015
.
Svete J., Grošelj U., Požgan F., Štefane B.
Synthesis,
2018
.
Prier C.K., Rankic D.A., MacMillan D.W.
Chemical Reviews,
2013
.
Crespi S., Fagnoni M.
Chemical Reviews,
2020
.
Wu Q., Bao X., Guo W., Wang B., Li Y., Luo H., Wang H., Ren N.
Biotechnology Advances,
2019
.
Xuan J., Zhang Z., Xiao W.
Angewandte Chemie - International Edition,
2015
.
Nguyen V.T., Haug G.C., Nguyen V.D., Vuong N.T., Arman H.D., Larionov O.V.
Chemical Science,
2021
.
Dang H.T., Haug G.C., Nguyen V.T., Vuong N.T., Nguyen V.D., Arman H.D., Larionov O.V.
ACS Catalysis,
2020
.
Dmitriev I.A., Levin V.V., Dilman A.D.
Organic Letters,
2021
.
Ravelli D., Fagnoni M., Fukuyama T., Nishikawa T., Ryu I.
ACS Catalysis,
2017
.
Strieth-Kalthoff F., James M.J., Teders M., Pitzer L., Glorius F.
Chemical Society Reviews,
2018
.
Nguyen V.T., Nguyen V.D., Haug G.C., Vuong N.T., Dang H.T., Arman H.D., Larionov O.V.
Angewandte Chemie - International Edition,
2020
.
Noyori R., Katô M., Kawanisi M., Nozaki H.
Tetrahedron,
1969
.
Matsuo B.T., Oliveira P.H., Correia J.T., Paixão M.W.
Organic Letters,
2021
.
Matsuo B.T., Correia J.T., Paixão M.W.
Organic Letters,
2020
.
Xia P., Ye Z., Song D., Ren J., Wu H., Xiao J., Xiang H., Chen X., Yang H.
Chemical Communications,
2019
.
Deepthi A., Thomas N.V., Sruthi S.L.
New Journal of Chemistry,
2021
.
Karmakar S., Silamkoti A., Meanwell N.A., Mathur A., Gupta A.K.
Advanced Synthesis and Catalysis,
2021
.
Yousfi T., Elliott A., Hanane M., Merdes R., Moyano A.
Molecules,
2016
.
Suárez A., Downey C.W., Fu G.C.
Journal of the American Chemical Society,
2005
.
Shintani R., Soh Y., Hayashi T.
Organic Letters,
2010
.
Na R., Jing C., Xu Q., Jiang H., Wu X., Shi J., Zhong J., Wang M., Benitez D., Tkatchouk E., Goddard W.A., Guo H., Kwon O.
Journal of the American Chemical Society,
2011
.
Blair L.M., Sperry J.
Journal of Natural Products,
2013
.
Wang M., Huang Z., Xu J., Chi Y.R.
Journal of the American Chemical Society,
2014
.
Nguyen V.D., Trevino R., Greco S.G., Arman H.D., Larionov O.V.
ACS Catalysis,
2022
.
Budnikov A.S., Lopat’eva E.R., Krylov I.B., Segida O.O., Lastovko A.V., Ilovaisky A.I., Nikishin G.I., Glinushkin A.P., Terent’ev A.O.
Journal of Agricultural and Food Chemistry,
2022
.
Zhilyaev K.A., Lipilin D.L., Kosobokov M.D., Samigullina A.I., Dilman A.D.
Advanced Synthesis and Catalysis,
2022
.
Adili A., Korpusik A.B., Seidel D., Sumerlin B.S.
Angewandte Chemie - International Edition,
2022
.
Nguyen V.T., Haug G.C., Nguyen V.D., Vuong N.T., Karki G.B., Arman H.D., Larionov O.V.
Chemical Science,
2022
.
Leleu L., Martzel T., Fall A., Sanselme M., Levacher V., Oudeyer S., Brière J.
Chemical Communications,
2022
.
Wang H., Zheng C., Chai Z., Zhang J., Zhao G.
Nature Communications,
2016
.
Ahsan M.J., Ali A., Ali A., Thiriveedhi A., Bakht M.A., Yusuf M., Salahuddin, Afzal O., Altamimi A.S.
ACS Omega,
2022
.
Qiu G., Kuang Y., Wu J.
Advanced Synthesis and Catalysis,
2014
.
Kawai H., Kusuda A., Nakamura S., Shiro M., Shibata N.
Angewandte Chemie - International Edition,
2009
.
Shpigel N.Y., Winkler M., Saran A., Zrv G.
Journal of Veterinary Medicine Series A,
1996
.
Oudeyer S., Levacher V., Beucher H., Brière J.
Molecules,
2023
.
Mokbel S.A., Fathalla R.K., El-Sharkawy L.Y., Abadi A.H., Engel M., Abdel-Halim M.
Bioorganic Chemistry,
2020
.
Bailly C., Hecquet P., Kouach M., Thuru X., Goossens J.
Bioorganic and Medicinal Chemistry,
2020
.
Asif M., Imran M., Husain A.
Journal of the Chilean Chemical Society,
2021
.
Moses V.S., Bertone A.L.
Veterinary Clinics of North America. Equine Practice,
2002
.
Dang H.T., Nguyen V.D., Haug G.C., Arman H.D., Larionov O.V.
JACS Au,
2023
.
Li J., Carli L., Kyne S., Chan P.
Advanced Synthesis and Catalysis,
2023
.
Paixao M.W., Gonçalves R.O., Ramos de Oliveira P.H., Ludtke D., de Jesus I.S., Debia N.P.
Organic and Biomolecular Chemistry,
2023
.
Leandro de Araujo J.G., Bezerra da Silva M.D., Celeste Viana Bento J.C., Medeiros de Azevêdo A., de Morais Araújo A.M., Dantas dos Anjos A.S., Martinez Huitle C.A., Vieira Dos Santos E., Gondim A.D., Cavalcanti L.
Chemistry - A European Journal,
2023
.
Andrews J.A., Kalepu J., Palmer C.F., Poole D.L., Christensen K.E., Willis M.C.
Journal of the American Chemical Society,
2023
.
li J., Phetcharawetch J., Qi M., Kyne S.H., Kuhakarn C., Zhong B., Chan P.W.
New Journal of Chemistry,
2023
.
Qiu J., Li W., Li X., Cao Y., Pan C., Li H.
Organic Letters,
2023
.
Lipilin D.L., Zubkov M.O., Kosobokov M., Dilman A.
Chemical Science,
2024
.
Zhuang K., Haug G.C., Wang Y., Yin S., Sun H., Huang S., Trevino R., Shen K., Sun Y., Huang C., Qin B., Liu Y., Cheng M., Larionov O.V., Jin S., et. al.
Journal of the American Chemical Society,
2024
.
Singh P.P., Sinha S., Gahtori P., Tivari S., Srivastava V.
Organic and Biomolecular Chemistry,
2024
.
Rubanov Z.M., Levin V.V., Dilman A.D.
Organic Letters,
2024