Infrared Assisted Production of 3,4-Dihydro-2(1H)-pyridones in Solvent-Free Conditions

Noguez, Ma. Olivia; Marcelino, Vanessa; Rodríguez, Hortensia; Martin, Osnieski; Martínez, Joel; Arroyo, Gonzalo; Pérez, Francisco J.; Suárez, Margarita; Miranda, René

doi:10.3390/ijms12042641

Cited by 29 publications

(24 citation statements)

References 32 publications

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“…As part of our ongoing research program on the production of biologically active heterocyclic molecules using suitable green approaches, using mainly novel modes to activate reactions [15–19], we report, in this article, the development of 11 new boron-containing heterocyclic molecules. The first eight compounds 5a – c , 6a – c and 7b , c were prepared by adapting the H-4CR protocol, using regioisomers ( ortho , meta , and para ) of formylphenylboronic acid, three different β-dicarbonylic compounds, and ammonium acetate, using-comparatively mantle heating, and infrared and microwave irradiation as the activating modes, with a minimal quantity of ethanol (Scheme 1).…”

Section: Resultsmentioning

confidence: 99%

“…As part of our ongoing research program, we are interested in the green production of novel hybrid heterocyclic molecules in order to synergize or modify the pharmacological activities of the prototypes, mainly using microwave or near-infrared irradiation as the activating source, in the absence of solvents and using naturally occurring non-toxic catalysts, such as bentonitic clays [15–19]. The purpose of this work is to investigate the one-pot green production of various hybrid-BCCs related to a set of eight novel 1,4-dihydropyridines 5a – c , 6a – c , 7b , c (BCDHPy; Scheme 1) and to a set of three 3,4-dihydropyrimidinones 9a – c (BCDHPm, Scheme 2), all derivatives of o , m , or p -boronic acids, using three different modes of activation (mantle heating, microwave irradiation, or near-infrared irradiation), in the presence of ethanol, which is a green solvent according to the TRI-EPA (Toxics Release Inventory-Environmental Protection Agency) [20].…”

Section: Introductionmentioning

confidence: 99%

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Green Approach—Multicomponent Production of Boron—Containing Hantzsch and Biginelli Esters

Martínez

Romero-Vega

Abeja-Cruz

et al. 2013

IJMS

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Multicomponent reactions are excellent methods that meet the requirements of green chemistry, by reducing the number of steps, and consequently reducing purification requirements. Accordingly, in this work, 11 novel hybrid-boron-containing molecules, namely eight 1,4-dihydropyridines and three 3,4-dihydropyrimidinones, derived from formylphenylboronic acids (ortho, meta and para), were obtained using a green approach, involving H-4CR and B-3CR practices, in the presence of ethanol, which is a green solvent, and using three comparatively different modes of activation (mantle heating, yield 3%–7% in 24 h, Infrared Radiation (IR) irradiation, yield 12%–17% in 12 h, and microwave irradiation, yield 18%–80%, requiring very low reaction times of 0.25–0.33 h). In addition, as a green-approach is offered, a convenient analysis, of the 12 green chemistry principles for the overall procedure was performed. Finally, since all the products are new, characterizations were carried out using common analytic procedures (1H, 11B, and 13C NMR, FAB+MS, HRMS, and IR). The accurate mass data of unexpected ions related to interactions between thioglycerol and the expected products, in the FAB+-mode, enabled unequivocal characterization of the target molecules.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Green Approach—Multicomponent Production of Boron—Containing Hantzsch and Biginelli Esters

Martínez

Romero-Vega

Abeja-Cruz

et al. 2013

IJMS

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“…In addition, BCC have been used to target biomolecules involved in cancer therapy, including through non‐specific applications (such as boron neutron capture therapy) and direct selective action on some cancer targets . As a part of our ongoing research program, we are interested in developing green chemistry protocols for the production of novel hybrid heterocyclic molecules with possible pharmacological activity, mainly in the absence of solvent and using microwave or infrared irradiation to activate the reactions . These synthesized molecules are characterized by mass spectrometry …”

Section: Methodsmentioning

confidence: 99%

Thioglycerol matrix interactions in the positive ion fast atom bombardment mass spectrometry of several Hantzsch and Biginelli ester derivatives of boronic acids

Martínez¹,

Abarca²,

Pérez

et al. 2013

Rapid Comm Mass Spectrometry

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“…As part of our ongoing research program, we are interested in the development of green chemistry approaches, in order to produce novel hybrid heterocyclic molecules, with possible pharmacological activities; and, complementarily, to conduct mass spectrometric studies of these molecules …”

Section: Introductionmentioning

confidence: 99%

Alternative mass spectrometry techniques for the validation of the fragmentation pattern of capsaicin and dihydrocapsaicin

Rosas¹,

Martínez

Alonso

et al. 2019

Rapid Comm Mass Spectrometry

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Rationale Capsaicinoids are prevalent secondary metabolites in many natural and synthetic pharmacological compounds. To date, several soft ionization studies related to capsaicinoids have been reported; they all proposed a common fragmentation pattern based on a rearrangement of the aromatic double bonds and the fragmentation of the various positional acyl chains. However, the mechanism has never been validated by high‐resolution analyses. Consequently, in this work, a validated fragmentation mechanism of the main capsaicinoids, capsaicin (1) and dihydrocapsaicin (2), is offered. Methods In order to propose and validate a common electron ionization (EI) fragmentation mechanism for the target analytes, the following mass spectrometric methods were employed: collision‐induced dissociation (CID) by means of linked scans (LS), reinforcing the methodology by high‐resolution mass spectrometry (HRMS), in addition to appropriate deuterium‐labeled experiments performed using gas chromatography/mass spectrometry (GC/MS) and direct analysis in real time (DART). Results In a first stage, a common EI fragmentation pattern comprising two pathways was proposed for compounds 1 and 2; then, the suggested mechanism was validated by CID‐LS together with HRMS complemented by DART‐deuterium‐labeling studies. The obtained results are indicative that the corresponding molecular ions were conveniently observed, m/z 305 and m/z 307; it is worth noting that the common base peak is in correspondence with a tropylium ion derivative (m/z 137), as a consequence of a McLafferty rearrangement. In addition to these highlighted fragments, other common ions, m/z 122 and m/z 94, and their corresponding trajectory, were confirmed using the same approach. Finally, the proposed mechanism was complementarily validated by deuterium‐labeling studies, taking into account the two exchangeable hydrogens present in the phenolic and the amidic moieties. Conclusions A common validated EI fragmentation pattern for both capsaicin and dihydrocapsaicin was established using appropriated mass spectrometric methods together with convenient hydrogen/deuterium labeling. This study provides a new alternative to validate mechanisms of fragmentation of important natural products.

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Infrared Assisted Production of 3,4-Dihydro-2(1H)-pyridones in Solvent-Free Conditions

Cited by 29 publications

References 32 publications

Green Approach—Multicomponent Production of Boron—Containing Hantzsch and Biginelli Esters

Green Approach—Multicomponent Production of Boron—Containing Hantzsch and Biginelli Esters

Thioglycerol matrix interactions in the positive ion fast atom bombardment mass spectrometry of several Hantzsch and Biginelli ester derivatives of boronic acids

Alternative mass spectrometry techniques for the validation of the fragmentation pattern of capsaicin and dihydrocapsaicin

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