Revisiting the Betti Synthesis: Using a Cheap, Readily Available, Recyclable Clay Catalyst under Solventless Conditions

Bosica, Giovanna; Abdilla, Roderick; Demanuele, Kaylie

doi:10.1002/ejoc.201800826

Cited by 16 publications

(6 citation statements)

References 45 publications

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“…Reactions were conducted at 60 °C in neat conditions. The use of proline as an amine resulted in yields ranging from 50 to 91% in 2-6 h. Morpholine and piperidine also worked to give the products in 4-12 h, at yields of 86-90% [91]. It is also This reaction can also be easily catalysed by the commercially available Montmorillonite K30 clay catalyst.…”

Section: Mannich-type Reactionsmentioning

confidence: 92%

“…Reactions were conducted at 60 • C in neat conditions. The use of proline as an amine resulted in yields ranging from 50 to 91% in 2-6 h. Morpholine and piperidine also worked to give the products in 4-12 h, at yields of 86-90% [91]. It is also possible to use amides instead of amines, as Lei et al did when they succeeded in making use of graphite-supported perchloric acid (Figure 38).…”

Section: Mannich-type Reactionsmentioning

confidence: 98%

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Recent Advances in Multicomponent Reactions Catalysed under Operationally Heterogeneous Conditions

Bosica

Abdilla

2022

Catalysts

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Multicomponent reactions (MCRs) have been gaining significance and attention over the past decade because of their ability to furnish complex products by using readily available and simple starting materials while simultaneously eliminating the need to separate and purify any intermediates. More so, most of these products have been found to exhibit diverse biological activities. Another paradigm shift which has occurred contemporarily is the switch to heterogeneous catalysis, which results in additional benefits such as the reduction of waste and an increase in the safety of the process. More importantly, it allows the user to recover and reuse the catalyst for multiple runs. In summary, both methodologies adhere to the principles of green chemistry, a philosophy which needs to become overarchingly enshrined. The plethora of reactions and catalysts which have been developed gives hope that chemists are slowly changing their ideology. As a result, this review attempts to discuss multicomponent reactions catalysed by operationally heterogeneous catalysts in the past 10 years. In this review, a further distinction is made between the MCRs which lead to the formation of heterocycles and those which do not.

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Section: Mannich-type Reactionsmentioning

confidence: 92%

Section: Mannich-type Reactionsmentioning

confidence: 98%

Recent Advances in Multicomponent Reactions Catalysed under Operationally Heterogeneous Conditions

Bosica

Abdilla

2022

Catalysts

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“…Higher temperature is required for this reaction than the amine analogues due to the un-reactivity of amides (Scheme 7). [45] Aza-Henry is an another type of Mannich Reaction, that involves the reaction of amines, aldehydes, and nitroalkanes. The application of CuI supported on Amberlyst A21 was documented for such a reaction, without the need of other solvents with yields ranging between 38-98 % (Scheme 8).…”

Section: Chemistryselectmentioning

confidence: 99%

“…Higher temperature is required for this reaction than the amine analogues due to the un‐reactivity of amides (Scheme 7). [45] …”

Section: Application Of Mannich Basesmentioning

confidence: 99%

Facile Multicomponent Mannich Reaction towards Biologically Active Compounds

Borah

Nath

et al. 2023

ChemistrySelect

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The Mannich reaction is one of the most broadly used organic reactions for constructing CÀ N and CÀ C bonds in synthetic chemistry. This review focuses on the multicomponent Mannich reaction and its variants for the synthesis of biologically active moieties such as anticancer, antimicrobial, antimalarial, antitubercular, anti-inflammatory and anticonvulsant molecules. A few organocatalyzed asymmetric Mannich reactions are also incorporated.[a] Dr. P. Borah CSIO Analytical facility, (CAF)(a), CSIR-

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“…The Betti bases reported in the current study were prepared according to our general synthetic pathway [16], which is outlined in Fig. 2.…”

Section: Chemistrymentioning

confidence: 99%

Naphthol-derived Betti bases as potential SLC6A14 blockers

Puerta¹,

Alexis²,

Abdilla³

et al. 2019

Journal of Molecular and Clinical Medicine

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Betti bases (aminobenzylnaphthols) have not been studied extensively to explore their possible pharmacological applications. Our group prepared a small and focused library of twenty-three Betti bases from the multicomponent reaction of 2-naphthol with primary or secondary cyclic amines and representative aromatic aldehydes. The compounds were prepared in 52-90% yield using environmentally friendly procedures. The E-factor and the atom economy for our process were 3.92 and 94%, respectively. The study of the anti-proliferative activity against human solid tumor cell lines pointed out that these Betti bases represent privileged scaffolds and could be used for the development of pharmacologically-active compounds in cancer therapeutics. The 50% growth inhibitory (GI 50 ) values of the most potent compounds were in the low micromolar range. Fourteen of these Betti bases were less active in HBL-100 breast cancer cells than towards the breast cancer cell line T-47D. A subset of these Betti bases was further tested against the human breast cancer cell lines MCF-7 and MDA-MB-453. The results indicated a correlation in the sensitivity of T-47D cells to Betti bases. We explored computationally the interaction of the Betti bases with SLC6A14, a Na + -and Cl − -dependent influx transporter of both neutral and cationic amino acids that is overexpressed in T-47D cells. SLC6A14 is inhibited by α-methyl-tryptophan, which blocks cell growth via deprivation of amino acid influx. The docking studies indicated that our Betti bases might behave as tryptophan mimetics, blocking this solute carrier transporter and inducing the anti-proliferative effects. Importantly, these Betti bases showed good cytotoxic selectivity towards cancer cells with no activity against normal human fibroblast cells BJ-hTERT.

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Revisiting the Betti Synthesis: Using a Cheap, Readily Available, Recyclable Clay Catalyst under Solventless Conditions

Cited by 16 publications

References 45 publications

Recent Advances in Multicomponent Reactions Catalysed under Operationally Heterogeneous Conditions

Recent Advances in Multicomponent Reactions Catalysed under Operationally Heterogeneous Conditions

Facile Multicomponent Mannich Reaction towards Biologically Active Compounds

Naphthol-derived Betti bases as potential SLC6A14 blockers

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