Corrigendum to “A mechanistic investigation of Biginelli reaction under base catalysis” [Tetrahedron Lett. 52 (2011) 3605–3609]

Raj, Monika; Rao, H. Surya Prakash; Manjunatha, Sulur G.; Sridharan, R.; Nambiar, Sudhir; Keshwan, Jaikumar; Rappai, Jayan; Bhagat, Sagar; Shwetha, B.S.; Hegde, Dinesh; Santhosh, U.

doi:10.1016/j.tetlet.2011.07.062

Cited by 24 publications

(6 citation statements)

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“…72 ESI-MS(/MS) has been proved to be an outstanding tool for reaction mechanism monitoring [73][74][75] with impressive results for the Biginelli reaction. 76,77 We have already used ESI-MS(/MS) as an unsurpassed tool in the mechanistic investigation of the Biginelli reaction. [39][40][41] ESI-MS(/MS) online monitoring was therefore used to investigate the mechanism of the Biginelli reaction using catalyst 1.…”

Section: Resultsmentioning

confidence: 99%

The Biginelli reaction under batch and continuous flow conditions: catalysis, mechanism and antitumoral activity

et al. 2015

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Two novel coordination polymers (CPs) have been synthesized, characterized and successfully applied as robust heterogeneous catalysts for the Biginelli multicomponent reaction to obtain 3,4dihydropyrimidin-2(1H)-one or thione (DHPMs) derivatives. The reaction was initially developed using both CPs and the Zn-based material showed much better catalytic activity. After the reaction optimization under batch conditions, a continuous flow protocol was developed and applied with impressive results. Four bioactive DHPMs were successfully synthesized with high yields. The mechanism of the transformation was also investigated by electrospray (tandem) mass spectrometry (ESI-MS(/MS)) analyses. Online monitoring of the reaction indicated under the developed conditions that the iminium mechanism is preferred over the enamine-and Knoevenagel-based mechanisms. Nine DHPMs had their antitumoral activities evaluated against MCF-7 (human breast cancer cells), A549 (human alveolar basal epithelial cells) and Caco-2 (human epithelial colorectal cells) cancer cell lineages. Fibroblasts (healthy cells) were not affected by the tested DHPMs showing an excellent selectivity for tumour cells. Three DHPMs returned impressive results, being capable of inhibiting tumour cell proliferation in 72 h.

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Section: Resultsmentioning

confidence: 99%

The Biginelli reaction under batch and continuous flow conditions: catalysis, mechanism and antitumoral activity

et al. 2015

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“…Readers can find a survey about the chronological advancements of the mechanistic hypothesis in previous, very interest-ing reviews. [8,55] Nowadays, theoretical DFT (density functional theory) [69][70][71] and AFIR (artificial force induced reaction) [72] studies corroborating combined NMR and ESI-MS/MS [73,74] experiments have established that all of these three mechanisms are consistent and possible, even in the same reaction. They all give rise to the same final product, but the prevalence of one of them strictly depends on the catalyst and, less strongly, on the solvent of the reaction.…”

Section: The Biginelli Reactionmentioning

confidence: 98%

“…[76] On the contrary, an enamine pathway is the preferred way to DHPMs when the catalyst is a base. [68,73] The Knoevenagel pathway is the less probable mechanism, as the energetic barrier for the Knoevenagel intermediate is the highest among all. [69][70][71] It can only be observed in few cases, as for example when the catalytic system is an heteropolyacids in presence of embedded imidazolium based ionic liquid as BMI•PF 3 .…”

Section: The Biginelli Reactionmentioning

confidence: 99%

Similarity and Competition between Biginelli and Hantzsch Reactions: an Opportunity for Modern Medicinal Chemistry

2020

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Similarity and competition between multicomponent reactions with similar mechanisms and leading to similar scaffolds can be a useful tool for medicinal chemistry. In this review, we have summarized the studies disclosing the mechanism of such competition between the Biginelli and Hantzsch reactions. We focused our attention in particular on those studies exploiting similarity and competition as an opportunity to switch from one reaction to another, by simply changing the reaction conditions, thus opening the possibility to obtain, using the same experimental setup, molecular libraries of both 3,4‐dihydropyrimidin‐2‐(1H)‐ones (DHPM) and 1,4‐dihydropyridines (1,4‐DHP) scaffolds. The aim of this review is to encourage further exploitation of such synthetic strategy as a tool for enhancing the chemical space in medicinal chemistry.

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“…Later, based on ESI-MS(/MS) analysis, a different mechanistic proposition for a base-catalysed Biginelli reaction showed a preferred reaction pathway favouring the enamine-like mechanism (Scheme 18). 20 Curiously, the intermediate of m/z 279 was detected and characterized in the positive ion mode, therefore in its protonated form, despite the fact that the reaction was basecatalysed.…”

Section: Scheme 10mentioning

confidence: 99%

What do we know about multicomponent reactions? Mechanisms and trends for the Biginelli, Hantzsch, Mannich, Passerini and Ugi MCRs

2014

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The current manuscript describes the importance, mechanism propositions, evidence and controversies associated with multicomponent reactions (MCRs). The following multicomponent reactions are presented and critically evaluated: The Biginelli, Hantzsch, Mannich, Passerini and Ugi reactions. The aim of this review is to highlight what we already know about the mechanisms associated with these MCRs and the evidence supporting the proposed reaction pathways. Controversies and prospects are also discussed herein.

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Corrigendum to “A mechanistic investigation of Biginelli reaction under base catalysis” [Tetrahedron Lett. 52 (2011) 3605–3609]

Cited by 24 publications

References 0 publications

The Biginelli reaction under batch and continuous flow conditions: catalysis, mechanism and antitumoral activity

The Biginelli reaction under batch and continuous flow conditions: catalysis, mechanism and antitumoral activity

Similarity and Competition between Biginelli and Hantzsch Reactions: an Opportunity for Modern Medicinal Chemistry

What do we know about multicomponent reactions? Mechanisms and trends for the Biginelli, Hantzsch, Mannich, Passerini and Ugi MCRs

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