Efficient Catalytic Hydrogenation of N‐Unsubstituted Cyclic Imides to Cyclic Amines

Maj, Anna; Suisse, Isabelle; Pinault, Nathalie; Robert, Nicolas; Agbossou‐Niedercorn, Francine

doi:10.1002/cctc.201402233

Cited by 19 publications

(8 citation statements)

References 64 publications

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“…4A6 ) 57 . The same year, Agbossou-Niedercorn and co-workers developed a heterogeneous [Rh 6 (CO) 6 /Mo(CO) 6 ]-catalyzed full hydrogenation of N-unsubstituted cyclic imides to the corresponding aliphatic cyclic amines 93 .…”

Section: Related Catalytic Hydrogenative Transformationsmentioning

confidence: 99%

Homogeneous and heterogeneous catalytic reduction of amides and related compounds using molecular hydrogen

et al. 2020

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Catalytic hydrogenation of amides is of great interest for chemists working in organic synthesis, as the resulting amines are widely featured in natural products, drugs, agrochemicals, dyes, etc. Compared to traditional reduction of amides using (over)stoichiometric reductants, the direct hydrogenation of amides using molecular hydrogen represents a greener approach. Furthermore, amide hydrogenation is a highly versatile transformation, since not only higher amines (obtained by CO cleavage), but also lower amines and alcohols, or amino alcohols (obtained by C-N cleavage) can be selectively accessed by fine tuning of reaction conditions. This review describes the most recent advances in the area of amide hydrogenation using H 2 exclusively and molecularly defined homogeneous as well as nanostructured heterogeneous catalysts, with a special focus on catalyst development and synthetic applications. T he development of green and sustainable methods is a central focus of modern organic synthesis and its applications in various areas of the chemical industry. In this respect, many reduction reactions, traditionally employing stoichiometric amounts of metal hydrides with inherent low atom efficiency 1 , can be favorably replaced by catalytic hydrogenations. In fact, the combination of molecular hydrogen and catalysts does not only allow avoiding formation of waste products 2 , it also opens the door to clean transformations based on renewable energies as the conversion of solar or wind energy to "green" hydrogen is likely to be implemented in the coming years. Among the many reduction reactions known, amide hydrogenation can be encountered as one of the most desired considering the importance of the derived amines in several branches of chemical industry. In fact, since the start of the Green Chemistry Institute Pharmaceutical Roundtable in the United States in 2005, several projects aimed to the achievement of a practical amide hydrogenation methodology have been supported 3,4. The long-term interest of the pharmaceutical industry in this specific transformation is explained by the fact that it ideally affords structurally complex amines, present in many of the currently employed drugs. Furthermore, amines are also in bulk and fine chemicals used in the manufacture of plastics, textiles, surfactants, dyes, and many more 5. Amides play a central role in the chemistry of life, as they are the key elements to generate peptides and proteins from amino acid monomers. At the same time, they are present in artificial

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Section: Related Catalytic Hydrogenative Transformationsmentioning

confidence: 99%

Homogeneous and heterogeneous catalytic reduction of amides and related compounds using molecular hydrogen

et al. 2020

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“…However, such a divergent strategy implies the reduction of azido groups in the presence of the chromophoric core. To avoid this potentially problematic reaction [ 27 ], here we have instead used a convergent synthetic procedure. In this approach the synthesis of the dendrimeric and chromophore structures are carried out first before being coupled together.…”

Section: Resultsmentioning

confidence: 99%

Fluorescent BAPAD Dendrimeric Antigens Are Efficiently Internalized by Human Dendritic Cells

et al. 2016

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A new fluorescent dendrimeric antigen (DeAn) based on a dendron with amoxicilloyl terminal groups was synthesized. The synthesis was carried out using a novel class of all-aliphatic polyamide dendrimer (BisAminoalkylPolyAmide Dendrimers, or BAPAD) involving the direct condensation of 3,3′-diazidopivalic acid as a building block. Iterative azide reduction/amide formation increases the dendrimer generation. The BAPAD dendrimer was designed with a cystamine core. Reduction of the disulfide bond allows the incorporation of BAPAD dendrons into a 1,8-naphthalimide functionalized with a maleimide group. The fluorescence properties of DeAn were studied in PBS and compared with the properties of an equivalent dendron possessing amino-terminal groups. Both molecules shown high fluorescence quantum yields in PBS and could readily be visualized by fluorescence microscopy. DeAn was used as a synthetic antigen in a biomedical assay that tests their potential as an amoxicillin carrier in drug internalization by dendritic cells (DC) from tolerant and allergic patients. Cytometry data suggest that the dendrons are non-toxic and easily internalized by DCs, while confocal microscopy images indicate that the compounds are preferentially accumulated in the cytoplasm. These results indicate that BAPAD dendrons are good candidates for synthetic scaffolds for biomedical applications.

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“…2 ). After the original report by Patton and Drago dealing with the hydrogenation of N -methylsuccinimide with a ruthenium catalyst, 5 alternative procedures were reported by the groups of Bruneau, 6 Ikariya, 7 Bergens, 8 García, 9 Agbossou-Niedercorn, 10 Xie, 11 Zhang 12 and our group. 13 These protocols afforded valuable products such as aliphatic lactams, 2-hydroxymethylbenzamides, ω-hydroxylactams, benzamides, aliphatic cyclic amines, 1,4-diols and isoindolinone derivatives directly from phthalimides.…”

Section: Introductionmentioning

confidence: 97%

Unprecedented selective homogeneous cobalt-catalysed reductive alkoxylation of cyclic imides under mild conditions

et al. 2017

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Efficient Catalytic Hydrogenation of N‐Unsubstituted Cyclic Imides to Cyclic Amines

Cited by 19 publications

References 64 publications

Homogeneous and heterogeneous catalytic reduction of amides and related compounds using molecular hydrogen

Homogeneous and heterogeneous catalytic reduction of amides and related compounds using molecular hydrogen

Fluorescent BAPAD Dendrimeric Antigens Are Efficiently Internalized by Human Dendritic Cells

Unprecedented selective homogeneous cobalt-catalysed reductive alkoxylation of cyclic imides under mild conditions

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