Gold Salts as Alternative Catalysts in Promoting Cascade Condensation of 2‑Aminobenzaldehydes with Alcohols and Amines

The distinctive features of gold self-relay catalysts were alternatively utilized in the intriguing cascade condensation of 2-aminobenzaldehydes with alcohols and amines. Using NaAuCl4·2H2O as a catalyst, a range of 13-alkyloxy-7,11b-dihydro-6H,13H-6,12-[1,2]­benzenoquinazolino­[3,4-a]­quinazoline d...

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Bibliographic Details
Published in:Journal of organic chemistry 2024-11, Vol.89 (22), p.16828-16837
Main Authors: Momoli, Caterina, Lamenta, Astrid, Chiarini, Marco, Demitri, Nicola, Lamba, Doriano, Morlacci, Valerio, Palombi, Laura, Arcadi, Antonio
Format: Article
Language:English
Subjects:
benzylamines
catalysts
catalytic activity
gold
organic chemistry
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Summary:The distinctive features of gold self-relay catalysts were alternatively utilized in the intriguing cascade condensation of 2-aminobenzaldehydes with alcohols and amines. Using NaAuCl4·2H2O as a catalyst, a range of 13-alkyloxy-7,11b-dihydro-6H,13H-6,12-[1,2]­benzenoquinazolino­[3,4-a]­quinazoline derivatives was produced in good to high yields through A3B condensation of various 2-aminobenzaldehydes with alcohols. By carefully choosing the reaction conditions, gold catalysis also proved effective for A2B condensation with primary aryl- and benzylamines, facilitating the synthesis of challenging McGeachin bisaminals, including a chiral nonracemic derivative of 2-(S)-methylbenzylamine. The mild conditions of this gold-catalyzed approach may lead to new advancements in the field.
ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/acs.joc.4c02162