Molybdenum‐Catalyzed One‐Pot Multi‐Step Synthesis of N ‐Polyheterocycles from Nitroarenes and Glycols

We report the efficient, sustainable one‐pot synthesis of a wide variety of N ‐polyheterocycles, such as imidazo‐quinolines and quinoxalines, and furoquinolines, from easily available nitroaromatics and glycols via a molybdenum catalytic domino reduction‐imine formation‐intramolecular cyclization‐ox...

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Published in:European journal of organic chemistry 2024-05, Vol.27 (18)
Main Authors: Gómez‐Gil, Sara, Cases, Nuria, Hernández‐Ruiz, Raquel, Rubio‐Presa, Rubén, Suárez‐Pantiga, Samuel, Pedrosa, María R., Sanz, Roberto
Format: Article
Language:English
Subjects:
Carbonyls
Chemical synthesis
Glycols
Molybdenum
Organic compounds
Oxidation
Quinoxalines
Reaction intermediates
Reducing agents
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container_issue 18
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container_title European journal of organic chemistry
container_volume 27
creator Gómez‐Gil, Sara
Cases, Nuria
Hernández‐Ruiz, Raquel
Rubio‐Presa, Rubén
Suárez‐Pantiga, Samuel
Pedrosa, María R.
Sanz, Roberto
description We report the efficient, sustainable one‐pot synthesis of a wide variety of N ‐polyheterocycles, such as imidazo‐quinolines and quinoxalines, and furoquinolines, from easily available nitroaromatics and glycols via a molybdenum catalytic domino reduction‐imine formation‐intramolecular cyclization‐oxidation sequence. It is worth highlighting that the recycling and incorporation of the waste carbonyl byproduct, generated in the reduction step, into the final compound is realized. In addition, the overall efficiency and atom economy of the process are further improved owing to the participation of one reaction intermediate as reductant that allows lowering the amount of external reducing agent employed.
doi_str_mv 10.1002/ejoc.202400145
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subjects Carbonyls
Chemical synthesis
Glycols
Molybdenum
Organic compounds
Oxidation
Quinoxalines
Reaction intermediates
Reducing agents
title Molybdenum‐Catalyzed One‐Pot Multi‐Step Synthesis of N ‐Polyheterocycles from Nitroarenes and Glycols
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