New reagent space and new scope for the Castagnoli–Cushman reaction of oximes and 3-arylglutaconic anhydrides

Bannykh, Anton; Levashova, Ekaterina; Bakulina, Olga; Krasavin, Mikhail

doi:10.1039/d2ob01675c

Cited by 2 publications

(1 citation statement)

References 24 publications

(51 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Subsequent stereoselective hydrogenation and lactam reduction produce challenging cis -configured 1,2,4-trisubstituted piperidines 91 ( Scheme 31 ) [ 62 , 63 ]. In addition, 3-Arylglutaconic acid anhydrides can also react with unprotected oximes to produce the corresponding N -hydroxylactams [ 64 ].…”

Section: Two-component Castagnoli–cushman Reactions (2c-ccr)mentioning

confidence: 99%

The Castagnoli–Cushman Reaction

et al. 2023

View full text Add to dashboard Cite

Since the first reports of the reaction of imines and cyclic anhydrides by Castagnoli and Cushman, this procedure has been applied to the synthesis of a variety of lactams, some of them with important synthetic or biological interest. The scope of the reaction has been extended to the use of various Schiff bases and anhydrides as well as to different types of precursors for these reagents. In recent years, important advances have been made in understanding the mechanism of the reaction, which has historically been quite controversial. This has helped to develop reaction conditions that lead to pure diastereomers and even homochiral products. In addition, these mechanistic studies have also led to the development of new multicomponent versions of the Castagnoli–Cushman reaction that allow products with more diverse and complex molecular structures to be easily obtained.

show abstract

Section: Two-component Castagnoli–cushman Reactions (2c-ccr)mentioning

confidence: 99%

The Castagnoli–Cushman Reaction

et al. 2023

View full text Add to dashboard Cite

show abstract

Concise Approach towards Tetramic Acid Derivatives via Ugi Reaction/Dieckmann Cyclization Sequence

Guranova,

Bakulina,

Kantin

et al. 2024

ChemistrySelect

Self Cite

View full text Add to dashboard Cite

Tetramic acids exhibit intriguing biological activity and are particularly attractive scaffolds for drug design. In this paper, we present a convenient approach based on the Dieckmann cyclization of Ugi adducts of malonic monoesters to afford a series of medically important polysubstituted tetramic acid derivatives. This simple and versatile method tolerates various substituents in both the amine, aldehyde and isocyanide moieties allowing the use of α‐substituted malonic acid monoesters. Examples of further functionalization of the free methylene group in the synthesized compounds have been presented.

show abstract

New reagent space and new scope for the Castagnoli–Cushman reaction of oximes and 3-arylglutaconic anhydrides

Abstract: The Castagnoli-Cushman reaction of oximes discovered earlier for homophthalic anhydride stimulated the search for other cyclic anhydrides which would be workable in that reaction. Finally, 3-arylglutaconic acid anhydrides were identified...

Cited by 2 publications

References 24 publications

The Castagnoli–Cushman Reaction

The Castagnoli–Cushman Reaction

Concise Approach towards Tetramic Acid Derivatives via Ugi Reaction/Dieckmann Cyclization Sequence

Contact Info

Product

Resources

About