2026-04-22T15:07:02Zhttps://riubu.ubu.es/oai/requestoai:riubu.ubu.es:10259/60912022-11-10T11:59:12Zcom_10259_3596com_10259_5086com_10259_2604com_10259_3593col_10259_3597col_10259_3594
Mo–Catalyzed One-Pot Synthesis of N-Polyheterocycles from Nitroarenes and Glycols with Recycling of the Waste Reduction Byproduct. Substituent-Tuned Photophysical Properties
Hernández Ruiz, Raquel
Rubio Presa, Rubén
Suarez Pantiga, Samuel
Pedrosa Sáez, María de los Remedios
Fernández Rodríguez, Manuel A.
Tapia Estévez, M" José
Sanz Díez, Roberto
Dioxomolybdenum
N-heterocycles
Nitroaromatics
Photophysical properties
Reuse of waste
Química orgánica
Chemistry, Organic
A catalytic domino reduction–imine formation–
intramolecular cyclization–oxidation for the general synthesis
of a wide variety of biologically relevant N-polyheterocycles,
such as quinoxaline- and quinoline-fused derivatives, and
phenanthridines, is reported. A simple, easily available, and
environmentally friendly dioxomolybdenum(VI) complex has
proven to be a highly efficient and versatile catalyst for
transforming a broad range of starting nitroarenes involving
several redox processes. Not only is this a sustainable, stepeconomical
as well as air- and moisture-tolerant method, but
also it is worth highlighting that the waste byproduct
generated in the first step of the sequence is recycled and
incorporated in the final target molecule, improving the
overall synthetic efficiency. Moreover, selected indoloquinoxalines
have been photophysically characterized in
cyclohexane and toluene with exceptional fluorescence
quantum yields above 0.7 for the alkyl derivatives.
Junta de Castilla y León and
FEDER (BU291P18 and BU049P20) and Ministerio de Economía y
Competitividad (MINECO) and FEDER (CTQ2016-75023-C2-1P)
for financial support. The project leading to these results has
also received funding from “la Caixa” Foundation, under the
agreement (LCF/PR/PR18/51130007) (CAIXA-UBU001). R.H.-R.
thanks Ministerio de Educación for a FPU predoctoral contract.
S.S P. thanks Junta de Castilla y León and FSE and FEDER for a
postdoctoral contract.
2021-11-04T09:48:41Z
2021-11-04T09:48:41Z
2021-09
info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
1521-3765
http://hdl.handle.net/10259/6091
10.1002/chem.202102000
eng
Chemistry – A European Journal. 2021, V. 27, n. 54, p. 13613-13623
https://doi.org/10.1002/chem.202102000
info:eu-repo/grantAgreement/Junta de Castilla y León//BU291P18
info:eu-repo/grantAgreement/Junta de Castilla y León//BU049P20
info:eu-repo/grantAgreement/Fundación Bancaria Caixa d'Estalvis i Pensions de Barcelona//LCF%2FPR%2FPR18%2F51130007 (CAIXA-UBU001)
info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2016-75023-C2-1-P/ES/DESARROLLO DE NUEVAS METODOLOGIAS SINTETICAS. APLICACION A LA PREPARACION DE MOLECULAS DE INTERES Y A LA VALORIZACION DE LA LIGNINA
Atribución-NoComercial 4.0 Internacional
http://creativecommons.org/licenses/by-nc/4.0/
info:eu-repo/semantics/openAccess
application/pdf
Wiley
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RIUBU. Repositorio Institucional de la Universidad de Burgos
http://hdl.handle.net/10259/6091