Work

Redrawing the Mannich‐Type Reaction through Carbonyl Umpolung Reactivity

Year: 2025

Type: article

Abstract: Herein, the development of an effective 3 starting materials–5 component reaction (3SM‐5CR) strategy is reported to assemble imidazolidine motifs from 1,2‐diaza‐1,3‐dienes, amines, and formaldehyde. In comparison with the classical Mannich‐type reactions (3SM‐6CR) for the construction of hexahydropyrimidines, this approach that uses azoalkene substrate (umpolung of carbonyl compound) as a donor/acceptor C1 synthon (carbene equivalent) enables practical construction of a library of previously inaccessible, structurally diverse imidazolidine derivatives with unprecedented ease. Inexpensive and easily available Lewis acid ZnCl 2 is an effective catalyst for these transformations, making this methodology flexible for the guided introduction of the amine components into the final N ‐heterocycles.

Source: Advanced Synthesis & Catalysis

DOI: 10.1002/adsc.70082

Authors: Vittorio Ciccone, Sara Caselli, Giacomo Mari, Fabio Mantellini, Gianfranco Favi

Institution: University of Urbino

Language: English

Topic: Multicomponent Synthesis of Heterocycles

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,650

Funders: European Commission, NextGenerationEU