Rapid access to pyrrolo[3,4-c]quinoline-1,3-diones: An improved synthetic protocol using a precursor prepared by Pfitzinger reaction
Abstract
An efficient pTSA-mediated cyclization cascade reaction of Pfitzinger's ester and benzoyl hydrazines has been developed providing a simple procedure for synthesis of pyrrolo [3,4-c]quinoline-1,3-dione derivatives. Unlike traditional synthetic protocol, this method avoids an additional step of conversion of quinoline-3,4-dicarboxylic acids to an anhydride, allowing direct reaction of ester derivative with hydrazine nucleophiles. © 2022 Elsevier Ltd
Keywords:
Acyl hydrazines / Cyclization / Isatin / Pfitzinger / pyrrolo[3,4-c]quinolineSource:
Tetrahedron, 2023Funding / projects:
- Ministry of Science, Technological Development and Innovation of the Republic of Serbia, institutional funding - 200122 (University of Kragujevac, Faculty of Science) (RS-MESTD-inst-2020-200122)
- Ministry of Science, Technological Development and Innovation of the Republic of Serbia, institutional funding - 200168 (University of Belgrade, Faculty of Chemistry) (RS-MESTD-inst-2020-200168)
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Institution/Community
VinčaTY - JOUR AU - Dimitrijević, Marina G. AU - Bogdanović, Goran A. AU - Trifunović, Snežana AU - Joksović, Milan D. PY - 2023 UR - https://vinar.vin.bg.ac.rs/handle/123456789/10609 AB - An efficient pTSA-mediated cyclization cascade reaction of Pfitzinger's ester and benzoyl hydrazines has been developed providing a simple procedure for synthesis of pyrrolo [3,4-c]quinoline-1,3-dione derivatives. Unlike traditional synthetic protocol, this method avoids an additional step of conversion of quinoline-3,4-dicarboxylic acids to an anhydride, allowing direct reaction of ester derivative with hydrazine nucleophiles. © 2022 Elsevier Ltd T2 - Tetrahedron T1 - Rapid access to pyrrolo[3,4-c]quinoline-1,3-diones: An improved synthetic protocol using a precursor prepared by Pfitzinger reaction DO - 10.1016/j.tet.2022.133236 ER -
@article{ author = "Dimitrijević, Marina G. and Bogdanović, Goran A. and Trifunović, Snežana and Joksović, Milan D.", year = "2023", abstract = "An efficient pTSA-mediated cyclization cascade reaction of Pfitzinger's ester and benzoyl hydrazines has been developed providing a simple procedure for synthesis of pyrrolo [3,4-c]quinoline-1,3-dione derivatives. Unlike traditional synthetic protocol, this method avoids an additional step of conversion of quinoline-3,4-dicarboxylic acids to an anhydride, allowing direct reaction of ester derivative with hydrazine nucleophiles. © 2022 Elsevier Ltd", journal = "Tetrahedron", title = "Rapid access to pyrrolo[3,4-c]quinoline-1,3-diones: An improved synthetic protocol using a precursor prepared by Pfitzinger reaction", doi = "10.1016/j.tet.2022.133236" }
Dimitrijević, M. G., Bogdanović, G. A., Trifunović, S.,& Joksović, M. D.. (2023). Rapid access to pyrrolo[3,4-c]quinoline-1,3-diones: An improved synthetic protocol using a precursor prepared by Pfitzinger reaction. in Tetrahedron. https://doi.org/10.1016/j.tet.2022.133236
Dimitrijević MG, Bogdanović GA, Trifunović S, Joksović MD. Rapid access to pyrrolo[3,4-c]quinoline-1,3-diones: An improved synthetic protocol using a precursor prepared by Pfitzinger reaction. in Tetrahedron. 2023;. doi:10.1016/j.tet.2022.133236 .
Dimitrijević, Marina G., Bogdanović, Goran A., Trifunović, Snežana, Joksović, Milan D., "Rapid access to pyrrolo[3,4-c]quinoline-1,3-diones: An improved synthetic protocol using a precursor prepared by Pfitzinger reaction" in Tetrahedron (2023), https://doi.org/10.1016/j.tet.2022.133236 . .