Synthesis of phenazines from ortho-bromo azo compounds via sequential Buchwald-Hartwig amination under micellar conditions and acid promoted cyclization

Yousif, Dawod; Monti, Mauro; Papagni, Antonio; Vaghi, Luca

doi:10.1016/j.tetlet.2020.152511

Cited by 11 publications

(10 citation statements)

References 25 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…This was beneficial for the kinetics (1 h vs. 20 h), but yields remained low to modest (Table 2, Entries 5-10). Temperature is another factor to consider in micellar procedures, as a slight increment could enormously increase reaction outputs [21]; obviously, the emulsion cloud point must not be exceeded, otherwise the micellar environment will be destroyed [31]. The temperature was increased to 60 • C and products 3aa-cb were obtained in excellent yields, ranging from 88 to 96% (Table 2, Entries 11-16).…”

Section: Resultsmentioning

confidence: 99%

“…micelles, enabling cross-coupling reactions without the need for deoxygenation of the reaction environment [17,18]. Within this context, we were interested in the preparation of thiophene-substituted anilines to be used as precursors for the synthesis of complex heterocyclic systems [19][20][21][22]. Beyond this, thiophene-substituted anilines also serve to produce conductive polymers [23] and as ligand precursors for coordination chemistry [24][25][26].…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Micellar Suzuki Cross-Coupling between Thiophene and Aniline in Water and under Air

et al. 2021

Self Cite

View full text Add to dashboard Cite

The Suzuki–Miyaura cross-coupling reaction plays a fundamental role in modern synthetic organic chemistry, both in academia and industry. For this reason, scientists continue to search for new, more effective, cheaper and environmentally friendly procedures. Recently, micellar synthetic chemistry has been demonstrated to be an excellent strategy for achieving chemical transformations in a more efficient way, thanks to the creation of nanoreactors in aqueous environments using selected surfactants. In particular, the cheap and commercially available surfactant Kolliphor EL (a polyethoxylated castor oil derivative) has been used with success to achieve metal-catalyzed transformations in water with high yields and short reaction times, with the advantage of using air-sensitive catalysts without the need for inert atmosphere. In this work, the Kolliphor EL methodology was applied to the Suzuki cross-coupling reaction between thiophene and aniline, using the highly effective catalyst Pd(dtbpf)Cl2. The cross-coupling products were achieved at up to 98% yield, with reaction times of up to only 15 min, working at room temperature and without the need for inert atmosphere.

show abstract

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Micellar Suzuki Cross-Coupling between Thiophene and Aniline in Water and under Air

et al. 2021

Self Cite

View full text Add to dashboard Cite

show abstract

“…Gels 2021, 7, x FOR PEER REVIEW 3 of 14 compounds [57][58][59][60], we prepared a set of bi-and trifunctional tetrazoles and applied them for the first time in the photoinduced cross-linking of porcine skin gelatin.…”

Section: Synthesis Of Cross-linking Agentsmentioning

confidence: 99%

“…However, it may be ideal as an effective cross-linking strategy to achieve improvements in the macroscopic characteristics of biological materials, such as gelatin. Intrigued by this possibility and exploiting our expertise in the synthesis of heterocyclic compounds [57][58][59][60], we prepared a set of bi-and trifunctional tetrazoles and applied them for the first time in the photoinduced cross-linking of porcine skin gelatin.…”

Section: Introductionmentioning

confidence: 99%

Photoinduced Porcine Gelatin Cross-Linking by Homobi- and Homotrifunctional Tetrazoles

Vaghi

Monti

Marelli³

et al. 2021

Gels

Self Cite

View full text Add to dashboard Cite

Gelatin is a costless polypeptide material of natural origin, able to form hydrogels that are potentially useful in biomaterial scaffold design for drug delivery, cell cultures, and tissue engineering. However, gelatin hydrogels are unstable at physiological conditions, losing their features only after a few minutes at 37 °C. Accordingly, treatments to address this issue are of great interest. In the present work, we propose for the first time the use of bi- and trifunctional tetrazoles, most of them unknown to date, for photoinduced gelatin cross-linking towards the production of physiologically stable hydrogels. Indeed, after UV-B irradiation, aryl tetrazoles generate a nitrilimine intermediate that is reactive towards different functionalities, some of them constitutively present in the amino acid side chains of gelatin. The efficacy of the treatment strictly depends on the structure of the cross-linking agent used, and substantial improved stability was observed by switching from bifunctional to trifunctional cross-linkers.

show abstract

“…Phenazine-derived compounds in nature are found in several bacterial genera found in marine and terrestrial environments (such as Streptomyces and Pseudomonas) [4], [11]. Synthetically, phenazine compounds are continuously researched and developed using various methods, types of constituent reactants, and the use of catalysts [12][13][14][15][16]. One of them is through the formation of benzo[a]pyrano[2,3-c] phenazine derivatives based on lawsone compounds.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and antioxidant activity of benzo[a]pyrano[2,3-c] phenazine derivative compound via one-pot multicomponent reaction

Liandi¹,

Cahyana²

2022

jrp

View full text Add to dashboard Cite

Phenazine derivative compounds are of concern because of their extraordinary activities in medicine. The aim of this study is to synthesize the derivative of benzo[a]pyrano[2,3-c] phenazine compound based on lawsone with caffeine catalyst using the one-pot multicomponent reaction method and test its antioxidant activity. The formation of the target compound was evaluated for functional group vibration, maximum wavelength, and molecular weight by FTIR, UV-Vis Spectrophotometer, and LCMS, which showed the characteristics of the benzo[a]pyrano[2,3-c] phenazine compound. The synthesized compound was 3-amino-2-cyano-1-(2-hydroxyl-phenyl)-1H-benzo[a]pyrano[2,3-c] phenazine with the molecular formula C26H16N4O2. At the optimum condition of the reaction, the use of caffeine catalyst was able to give a product yield of 67.2%. The potential of the synthesized compound as an antioxidant could be classified as a good antioxidant with an IC50 value of 14.26 ppm.

show abstract

Synthesis of phenazines from ortho-bromo azo compounds via sequential Buchwald-Hartwig amination under micellar conditions and acid promoted cyclization

Cited by 11 publications

References 25 publications

Micellar Suzuki Cross-Coupling between Thiophene and Aniline in Water and under Air

Micellar Suzuki Cross-Coupling between Thiophene and Aniline in Water and under Air

Photoinduced Porcine Gelatin Cross-Linking by Homobi- and Homotrifunctional Tetrazoles

Synthesis and antioxidant activity of benzo[a]pyrano[2,3-c] phenazine derivative compound via one-pot multicomponent reaction

Contact Info

Product

Resources

About