Selenoamides as powerful scaffold to build imidazo[1,5-a]pyridines using a grinding protocol

Ramírez-Gómez, Antonio; Gutiérrez-Hernández, Alejandro I.; Alvarado-Castillo, Miguel A.; Toscano, Rubén A.; Ortega‐Alfaro, M. Carmen; López‐Cortés, José G.

doi:10.1016/j.jorganchem.2020.121315

Cited by 3 publications

(5 citation statements)

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“…Ramírez‐Gómez et al. reported that the C=Se bond can be activated with iodine at room temperature, in grinding conditions, to obtain a family of impy products in excellent yields in only 1min of reaction time through mechanochemical synthesis (solvent‐free conditions) [79] …”

Section: Discussionmentioning

confidence: 99%

“…Ramírez-Gómez et al reported that the C=Se bond can be activated with iodine at room temperature, in grinding conditions, to obtain a family of impy products in excellent yields in only 1min of reaction time through mechanochemical synthesis (solvent-free conditions). [79] Very recently, two complementary synthetic routes have been reported to obtain 1-phosphine-impy ligands for use in Suzuki-Miyaura cross-coupling reactions (see Scheme 15). [80] This is the first synthetic procedure reported to collect a 1phosphine-impy nucleus in high yield, the obtained products Scheme 11.…”

Section: Methodsmentioning

confidence: 99%

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Luminescent Imidazo[1,5‐a]pyridine Scaffold: Synthetic Heterocyclization Strategies‐Overview and Promising Applications

Volpi

2022

Asian J Org Chem

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In the last few years, imidazo[1,5‐a]pyridine derivatives have attracted growing attention due to their remarkable emissive behaviours, structural modification and biological properties. Previously published works emphasize the possible technological applications of this luminescent scaffold and demonstrate the stringent relationship between chemical substituents and optical properties. The main goal of this work is to provide a complete list of the reported achievements concerning these promising heterocyclization reactions obtained starting from a huge variety of reagents, catalysts, oxidants, dehydrating agents involved in various reaction conditions. Particular attention is focused on the final possible substitutions, conjugations and structural modifications of the reported synthetic approaches, a powerful aspect to design innovative and employable new luminescent imidazo[1,5‐a]pyridine products.

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Section: Discussionmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Luminescent Imidazo[1,5‐a]pyridine Scaffold: Synthetic Heterocyclization Strategies‐Overview and Promising Applications

Volpi

2022

Asian J Org Chem

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“…Many of the developed synthetic approaches encountered certain limitations, often associated with the use of various catalysts such as Se(IV) [ 38 , 220 , 221 ], Pd(II) [ 222 , 223 ], Fe(II) and Fe(III) [ 224 , 225 ], Cu(II) ion [ 226 , 227 , 228 , 229 ], CuCl 2 [ 230 , 231 , 232 ], copper/iodine [ 233 ], Cu-MOF structures [ 234 , 235 ], boron trifluoride etherate [ 236 ], CBr 4 [ 237 ] or MnO 2 [ 53 ]. In addition, some catalysts require further reagents or co-catalysts such as selenium dioxide [ 238 ], dehydrating agents (e.g., molecular sieves [ 239 ] or propane phosphoric acid anhydride [ 213 ]), Lewis acids (BF 3 ), or oxidant agents (e.g., oxygen, iodine [ 240 , 241 ], elemental sulfur [ 242 ], or tert -butylperoxybenzoate) [ 243 ].…”

Section: Imidazopyridines: Different Synthetic Approachesmentioning

confidence: 99%

Imidazopyridine Family: Versatile and Promising Heterocyclic Skeletons for Different Applications

Volpi,

Laurenti,

Rabezzana

2024

Molecules

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In recent years, there has been increasing attention focused on various products belonging to the imidazopyridine family; this class of heterocyclic compounds shows unique chemical structure, versatile optical properties, and diverse biological attributes. The broad family of imidazopyridines encompasses different heterocycles, each with its own specific properties and distinct characteristics, making all of them promising for various application fields. In general, this useful category of aromatic heterocycles holds significant promise across various research domains, spanning from material science to pharmaceuticals. The various cores belonging to the imidazopyridine family exhibit unique properties, such as serving as emitters in imaging, ligands for transition metals, showing reversible electrochemical properties, and demonstrating biological activity. Recently, numerous noteworthy advancements have emerged in different technological fields, including optoelectronic devices, sensors, energy conversion, medical applications, and shining emitters for imaging and microscopy. This review intends to provide a state-of-the-art overview of this framework from 1955 to the present day, unveiling different aspects of various applications. This extensive literature survey may guide chemists and researchers in the quest for novel imidazopyridine compounds with enhanced properties and efficiency in different uses.

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“…R O Cr(CO) 5 With the aminocarbene complexes in hand, we carried out their selenative demetalation to obtain the arylselenoamides (3a-h), using the protocol earlier developed by our group for synthesizing ferrocenyl selenoamides. 13,31 This procedure provided the new arylselenoamides as yellow-red solids, in 15 to 45 min, depending on the ethoxy carbene complex used as precursor (Table S1, SI). To increase the global yields of these compounds, we attempted a two-step, one-pot synthesis based on the aminolysis-demetalation reaction as a key strategy.…”

Section: Table 1 Synthesis Of Ethoxycarbene Complexes (1a-h) and Aminocarbene Complexes (2a-h)mentioning

confidence: 99%

“…Compounds 1a, 1b, 1c, 1d, 1f, 1g and 1h are known and their spectroscopic data matched well with that already described in the literature. 13,[27][28][29][30][31] Synthesis of selenoamides (3a-h) in one-pot two-step conditions…”

Section: Synthesis Of Fischer Type-carbene Chromium(0) Complexes 1(a-h)mentioning

confidence: 99%

Synthesis of new heterocycle-based selenoamides as potent cytotoxic agents

López¹,

Gutiérrez-Hernández²,

Toscano³

et al. 2020

Arkivoc

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We report the synthesis of a new series of aryl-and heteroaryl (hydroxy)ethyl selenoamides, in a two-step, one-pot sequence based on the aminolysis/selenative demetalation of Fischer ethoxycarbene complexes, in good to excellent global yields, as small cytotoxic molecules. The molecular structure of a 2-thienyl based selenoamide was confirmed by single-crystal X-Ray diffraction analysis. In vitro analysis against different human cancer (HCT-15, U251 and PC-3) and human T-lymphocyte (MT2) cell lines revealed that the 2-thienyl based selenoamide can be considered a potent and selective compound against the human prostatic adenocarcinoma (PC-3) cell line with an IC50 value of 14.5 µM.

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Selenoamides as powerful scaffold to build imidazo[1,5-a]pyridines using a grinding protocol

Cited by 3 publications

References 68 publications

Luminescent Imidazo[1,5‐a]pyridine Scaffold: Synthetic Heterocyclization Strategies‐Overview and Promising Applications

Luminescent Imidazo[1,5‐a]pyridine Scaffold: Synthetic Heterocyclization Strategies‐Overview and Promising Applications

Imidazopyridine Family: Versatile and Promising Heterocyclic Skeletons for Different Applications

Synthesis of new heterocycle-based selenoamides as potent cytotoxic agents

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