Molybdenum-Catalyzed Synthesis of Nitrogenated Polyheterocycles from Nitroarenes and Glycols with Reuse of Waste Reduction By-product

A novel domino reduction/imine formation/intramolecular cyclization/oxidation for the efficient synthesis of pyrrolo(indolo)[1,2-a]quinoxalines and pyrrolo(indolo)[3,2-c]-quinolines from readily available nitrobenzenes and glycols is reported. The process utilizes the carbonyl byproduct of the initi...

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Bibliographic Details
Authors: Rubio Presa, Rubén, Pedrosa Sáez, María de los Remedios, Fernández Rodríguez, Manuel A., Arnáiz García, Francisco Javier, Sanz Díez, Roberto
Format: article
Status:Versión aceptada para publicación
Publication Date:2017
Country:España
Institution:Universidad de Burgos (UBU)
Repository:Repositorio Institucional de la Universidad de Burgos (RIUBU)
OAI Identifier:oai:riubu.ubu.es:10259/4924
Online Access:http://hdl.handle.net/10259/4924
Access Level:Open access
Keyword:Química orgánica
Chemistry, Organic
Description
Summary:A novel domino reduction/imine formation/intramolecular cyclization/oxidation for the efficient synthesis of pyrrolo(indolo)[1,2-a]quinoxalines and pyrrolo(indolo)[3,2-c]-quinolines from readily available nitrobenzenes and glycols is reported. The process utilizes the carbonyl byproduct of the initial dioxomolybdenum(VI)-catalyzed reduction of nitroaromatics with glycols as a reagent for the imine generation. This method represents the first sustainable domino reaction for the preparation of biologically relevant heterocycles that internally incorporates the waste formed in the first step to the final product.