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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Bibliographic Details
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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Summary: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.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202400145