Diastereoselective Synthesis of High Functionalized 4‐Imidazolidinone‐Tetrahydro‐β‐Carboline Hybrids via Divergent Post‐Ugi Transformation

An easily scalable and highly diastereoselective synthesis of challenging 1,2,5,6,11,11b‐hexahydro‐3H‐imidazo[1′,2′:1,2]pyrido[3,4‐b]indol‐3‐ones is accomplished through divergent transformation of Ugi 4‐CR products. The trimethylsilyl trifluoromethanesulfonate (TMSOTf) mediated intramolecular conde...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2024-05, Vol.366 (10), p.2376-2381
Main Authors: Morlacci, Valerio, Arcadi, Antonio, Aschi, Massimiliano, Chiarini, Marco, Demitri, Nicola, Lamba, Doriano, Momoli, Caterina, Palombi, Laura, Vece, Vito
Format: Article
Language:English
Subjects:
4-imidazolidinones
Adducts
Condensates
N-acylimidinium intermediates
Organic chemistry
Post-Ugi cyclization
Stereoselectivity
Synthesis
TMSOTf
β-carbolines
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Summary:An easily scalable and highly diastereoselective synthesis of challenging 1,2,5,6,11,11b‐hexahydro‐3H‐imidazo[1′,2′:1,2]pyrido[3,4‐b]indol‐3‐ones is accomplished through divergent transformation of Ugi 4‐CR products. The trimethylsilyl trifluoromethanesulfonate (TMSOTf) mediated intramolecular condensation of a series of Ugi 4‐CR adducts generates a N‐acylimidinium intermediate which undergoes ring closure to selectively afford the target title compounds in good to high yields.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202400133