A facile access for the synthesis of some C-2 substituted imidazopyrazines by utilizing the palladium catalyzed Suzuki cross-coupling reaction under microwave irradiation

Joy, Muthipeedika Nibin; Savitha, Bhaskaran; Sajith, Ayyiliath M.; Bodke, Yadav D.; Venkatesh, Talavara; Khader, K.K. Abdul; Padusha, M. Syed Ali; Muralidharan, A.

doi:10.1016/j.cclet.2015.08.015

Cited by 12 publications

(3 citation statements)

References 24 publications

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“…In the year 2016, Joy et al [57] demonstrated a simple and efficient microwave promoted Suzuki cross-coupling reaction between 2-bromo-1H-imidazo[4,5-b]pyrazines 70 with various boronic acids 71 to construct C-2 substituted imidazopyrazines 72 using (A-ta phos) 2 PdCl 2 as catalyst and CsF as base in DME-H 2 O (4 : 1) solvent at 100 °C (Scheme 41). This methodology could tolerate various types of functional groups.…”

Section: Suzuki Reaction In Polar-nonpolar Mixture Solventmentioning

confidence: 99%

Recent Advances in Microwave‐assisted Cross‐Coupling Reactions

et al. 2022

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The carbon-carbon and carbon-heteroatom bond forming coupling reactions have a fundamental value for the organic chemistry, and, therefore, these reactions have been always among the most valuable and basic studies for the evolution of organic synthesis and are extensively used for the synthesis of practically valuable compounds. Currently, greener techniques have been pulled in the consideration of researchers due to the rising environmental concern. Nowadays, the modern synthetic chemists of both academia and industry are trying to design the desired target molecules by using eco-friendly methods. In this context, microwaveassisted organic synthesis (MAOS) is known as one of the most convenient and emerging technologies in synthetic chemistry. Microwave activation/heating is a very convenient technique from the viewpoint of green chemistry because it speeds up the reaction rates and provides a higher yield by reducing side reactions. The present review represents the literature survey from 2008 to 2021 that covers the latest trends of microwave-assisted CÀ C and CÀ heteroatom bond forming coupling reactions with greener prospects.

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Section: Suzuki Reaction In Polar-nonpolar Mixture Solventmentioning

confidence: 99%

Recent Advances in Microwave‐assisted Cross‐Coupling Reactions

et al. 2022

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“…[23] Inspired by these excellent pioneering work and encouraged by our recent work, we envision a one-pot cascade synthetic approach to the 6-unsubstituted phenanthridines by coupling of readily accessible 2'-bromoacetanilides and arylboronic acids catalyzed by Pd(OAc) 2 and followed by intramolecular annulation in a DMSO/K 2 S 2 O 8 system. Herein, we wish to report a new protocol where a Suzuki coupling [24] is performed first and the resulting intermediate is cyclized and dehydrogenated mediated by the DMSO/ K 2 S 2 O 8 system to afford the phenanthridines. In this regard, DMSO is used as both the carbon source and the reaction medium.…”

Section: Introductionmentioning

confidence: 99%

One‐pot Cascade Reaction for the Synthesis of Phenanthridines via Suzuki Coupling/C−H Oxidation/Aromatization

et al. 2020

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“…The development of new leads in drug-discovery programme is always initiated by the synthesis of novel molecules which displays excellent and a wide array of biological profiles because of the presence of some critical structural features in them. Some heterocyclic frameworks act as highly functionalized scaffolds which play a pivotal role in developing new leads in drug discovery [1,2]. Among the diverse assortment of heterocyclic compounds, N-(hetero)aryl oxazole analogues (Figure 1) display a wide spectrum of applications and hence are considered as vital architectures in the area of medicinal chemistry, material science and agrochemicals [3].…”

Section: Introductionmentioning

confidence: 99%

A modified approach for the synthesis of biologically relevant 5-substituted-2-N-aryl-1,3-oxazole derivatives in mild conditions

Udhayasurian

Sivakumar²,

Sajith

et al. 2020

Journal of Taibah University for Science

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We herein report a modified approach for the synthesis of some pharmacologically relevant oxazole derivatives linked with amides under mild conditions. The utilization of polymer-supported triphenylphosphine (poly-TPP) as a phosphine ligand for generating the key iminophosphorane intermediate was found to be vital for achieving the synthesis of oxazole in room temperature. This alternative approach relying on the cyclization reaction of readily available phenacyl azide and phenyl isothiocyanate rendered the oxazole derivative 3a in excellent yield. This methodology has been applied for the synthesis of a more decorated oxazole derivative 3b having ester functionality and was further converted to different amides under microwave irradiation in good to excellent yields in the later stage.

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A facile access for the synthesis of some C-2 substituted imidazopyrazines by utilizing the palladium catalyzed Suzuki cross-coupling reaction under microwave irradiation

Cited by 12 publications

References 24 publications

Recent Advances in Microwave‐assisted Cross‐Coupling Reactions

Recent Advances in Microwave‐assisted Cross‐Coupling Reactions

One‐pot Cascade Reaction for the Synthesis of Phenanthridines via Suzuki Coupling/C−H Oxidation/Aromatization

A modified approach for the synthesis of biologically relevant 5-substituted-2-N-aryl-1,3-oxazole derivatives in mild conditions

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