The Catalytic Regio- and Stereoselective Synthesis of 1,6-Diazabicyclo[4.3.0]nonane-2,7-diones

Lebrêne, Arthur; Martzel, Thomas; Gouriou, Laura; Sanselme, Morgane; Levacher, Vincent; Oudeyer, Sylvain; Afonso, Carlos; Loutelier‐Bourhis, Corinne; Brière, Jean‐François

doi:10.1021/acs.joc.1c00252

Cited by 2 publications

(3 citation statements)

References 38 publications

(38 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…A simple synthesis of 1,6‐ di‐aza‐ bicyclo[4.3.0]nonane‐2,7diones 29 – 30 was carried out by Lebrêne and his colleagues in 2021 via a DBU organocatalytic multi‐component Knoevenagel‐ aza‐ Michael‐cyclization condensation reaction of arylaldehyde 13 , Meldrum's acid 1 , with pyridazinone 27 or the noncyclic hydrazine 28 (Scheme 13). [24] …”

Section: Synthesis Of Five‐membered Heterocyclesmentioning

confidence: 99%

“…A simple synthesis of 1,6-di-aza-bicyclo[4.3.0]nonane-2,7diones 29-30 was carried out by Lebrêne and his colleagues in 2021 via a DBU organocatalytic multi-compo-nent Knoevenagel-aza-Michael-cyclization condensation reaction of arylaldehyde 13, Meldrum's acid 1, with pyridazinone 27 or the noncyclic hydrazine 28 (Scheme 13). [24] The catalyst-free one-pot method for the preparation of 2,5-diaryl-1-hydroxy-1H-imidazole-4-yl derivatives 32 via four-component reaction of hydroxylamine 31, benzonitriles 9, arylglyoxals 10, and Meldrum's acid 1 in EtOH under reflux condition was accomplished by Alizadeh-Bani and coworkers (Scheme 14). [25]…”

Section: Synthesis Of Five-membered Heterocycles 21 N-heterocyclic Co...mentioning

confidence: 99%

See 1 more Smart Citation

The Molecular Diversity Scope of Meldrum's Acid in Multicomponent Reactions

Ziarani,

Ebrahimi,

Mohajer

et al. 2023

ChemistrySelect

View full text Add to dashboard Cite

Multicomponent reactions (MCRs) have gained significant attention in the field of organic synthesis due to their ability to efficiently construct complex molecular structures in a single step. Among the reagents employed in MCRs, Meldrum's acid has emerged as a highly versatile and valuable starting material, offering a wide range of molecular diversity. This comprehensive review explores the molecular diversity scope of Meldrum's acid in various MCRs, focusing on its unique attributes and the greener aspects of its application. Meldrum's acid possesses several remarkable features that contribute to its suitability as a key component in MCRs. Its high acidity enables effective participation in a variety of chemical reactions, while its rigid structure provides stability and allows for precise control of the reaction pathways. Furthermore, the ability of Meldrum's acid to undergo both nucleophilic and electrophilic attacks makes it highly versatile in the construction of diverse molecular frameworks. Its low steric hindrance further enhances its reactivity, facilitating efficient bond formation. By surveying the literature from the last five years (2018–2022), we delve into the broad range of applications of Meldrum's acid in MCRs. The review encompasses the synthesis of various heterocyclic compounds, highlighting the significance of Meldrum's acid in achieving molecular diversity. Moreover, particular emphasis is placed on the greener aspects of utilizing Meldrum's acid, considering the growing demand for environmentally friendly synthetic approaches. This includes exploring greener solvents, milder reaction conditions, and reduced waste generation.

show abstract

Section: Synthesis Of Five‐membered Heterocyclesmentioning

confidence: 99%

Section: Synthesis Of Five-membered Heterocycles 21 N-heterocyclic Co...mentioning

confidence: 99%

The Molecular Diversity Scope of Meldrum's Acid in Multicomponent Reactions

Ziarani,

Ebrahimi,

Mohajer

et al. 2023

ChemistrySelect

View full text Add to dashboard Cite

show abstract

“…A DBU-catalyzed MCR was successfully applied in the synthesis of 1,6-diazabicyclo[4.3.0]nonane-2,7-diones with high stereocontrol [ 191 ]. The desired adduct was obtained with a diastereoisomeric ratio up to 95:5 favoring the cis derivative in the model reaction.…”

Section: Catalysis In Stereoselective Mcrsmentioning

confidence: 99%

Catalytic Approaches to Multicomponent Reactions: A Critical Review and Perspectives on the Roles of Catalysis

2021

View full text Add to dashboard Cite

In this review, we comprehensively describe catalyzed multicomponent reactions (MCRs) and the multiple roles of catalysis combined with key parameters to perform these transformations. Besides improving yields and shortening reaction times, catalysis is vital to achieving greener protocols and to furthering the MCR field of research. Considering that MCRs typically have two or more possible reaction pathways to explain the transformation, catalysis is essential for selecting a reaction route and avoiding byproduct formation. Key parameters, such as temperature, catalyst amounts and reagent quantities, were analyzed. Solvent effects, which are likely the most neglected topic in MCRs, as well as their combined roles with catalysis, are critically discussed. Stereocontrolled MCRs, rarely observed without the presence of a catalytic system, are also presented and discussed in this review. Perspectives on the use of catalytic systems for improved and greener MCRs are finally presented.

show abstract

The Catalytic Regio- and Stereoselective Synthesis of 1,6-Diazabicyclo[4.3.0]nonane-2,7-diones

Cited by 2 publications

References 38 publications

The Molecular Diversity Scope of Meldrum's Acid in Multicomponent Reactions

The Molecular Diversity Scope of Meldrum's Acid in Multicomponent Reactions

Catalytic Approaches to Multicomponent Reactions: A Critical Review and Perspectives on the Roles of Catalysis

Contact Info

Product

Resources

About