Synthesis of pyrrolo-pyrrolo-pyrazines via the Pd/C-catalyzed cyclization of N-propargyl pyrrolinyl-pyrrole derivatives

Aslanoǧlu, Furgan; Başçeken, Sinan; Balcı, Metin

doi:10.1016/j.tetlet.2019.01.004

Cited by 9 publications

(4 citation statements)

References 28 publications

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“…In 2019, Balci et al ., built up a palladium catalyzed productive synthesis of N‐substituted dipyrrolo[1,2‐a : 20,10‐c]pyrazine derivatives (Scheme 43). Aromatization of the dihydropyrrole ring succeeded by Pd/C catalyzed intramolecular cyclization reaction among the alkyne functionality and the pyrrole nitrogen molecule under high temperature conditions outfitted the ideal dipyrrolo‐pyrazine skeleton [54] …”

Section: C−h Functionalization Of Pyrrolesmentioning

confidence: 99%

Recent Advances in Functionalization of Pyrroles and their Translational Potential

Hunjan

Panday

Gupta

et al. 2021

The Chemical Record

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Among the known aromatic nitrogen heterocycles, pyrrole represents a privileged aromatic heterocycle ranging its occurrence in the key component of “pigments of life” to biologically active natural products to active pharmaceuticals. Pyrrole being an electron‐rich heteroaromatic compound, its predominant functionalization is legendary to aromatic electrophilic substitution reactions. Although a few excellent reviews on the functionalization of pyrroles including the reports by Baltazzi in 1963, Casiraghi and Rassu in 1995, and Banwell in 2006 are available, they are fragmentary and over fifteen years old, and do not cover the modern aspects of catalysis. A review covering a comprehensive package of direct functionalization on pyrroles via catalytic and non‐catalytic methods including their translational potential is described. Subsequent to statutory yet concise introduction, the classical functionalization on pyrroles using Lewis acids largely following an ionic mechanism is discussed. The subsequent discussion follows the various metal‐catalyzed C−H functionalization on pyrroles, which are otherwise difficult to implement by Lewis acids. A major emphasize is given on the radical based pyrrole functionalization under metal‐free oxidative conditions, which is otherwise poorly highlighted in the literature. Towards the end, the current development of pyrrole functionalization under photocatalyzed and electrochemical conditions is appended. Only a selected examples of substrates and important mechanisms are discussed for different methods highlighting their scopes and limitations. The aromatic nucleophillic substitution on pyrroles (being an electron‐rich heterocycle) happened to be the subject of recent investigations, which has also been covered accentuating their underlying conceptual development. Despite great achievements over the past several years in these areas, many challenges and problems are yet to be solved, which are all discussed in summary and outlook.

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Section: C−h Functionalization Of Pyrrolesmentioning

confidence: 99%

Recent Advances in Functionalization of Pyrroles and their Translational Potential

Hunjan

Panday

Gupta

et al. 2021

The Chemical Record

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“…I am working with heterocyclic compounds containing pyrrole and pyrrole‐like compounds. Recently, we synthesized the heterocyclic compounds which include pyrrole and pyrazine by Pd/C catalyst [16]. In this study, I report initially propose synthesis steps for the compounds 1‐(2‐pyrrolidinone)‐butane‐1,3‐dione derivatives.…”

Section: Introductionmentioning

confidence: 99%

Design of 1‐(2‐pyrrolidinone)‐butane‐1,3‐dione derivatives and acetoxylation of these compound's methylene via hypervalent iodine (III)

Aslanoǧlu

2022

Journal of Heterocyclic Chem

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An interesting synthesis method for 2‐acetate‐1‐(2‐pyrrolidinone)‐butane‐1,3‐dione compounds was developed in this work. The synthesis of these compounds was carried out in three steps. In the first step, 2‐pyrrolidone derivatives were obtained by the Friedel‐Crafts reaction in presence of Eaton's reagent. Then, ‐NH group of 2‐pyrrolidone compounds were attached acetoacetate group in presence of 2,6‐trimethyl‐4H‐1,3‐dioxin‐4‐one reagent. Lastly, 1‐(2‐pyrrolidinone)‐butane‐1,3‐dione derivatives were reacted with Pida to attach acetoxy group to these compound's methylene.

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“…Among the heterogeneous Pd-based catalysts used in the Sonogashira cross-coupling, Pd/C is an effective and preferred choice due to its thermal stability, low cost, and large availability. 16,17 Our research program aims at developing efficient metal heterogeneous catalytic systems, 18−21 while we are also contributing to a circular economy approach working on biomass valorization. 22−25 Recently, we dedicated our attention to the valorization of urban waste and exploited biochar derived from local biomass as a viable alternative to carbonaceous supports for the preparation of Pd-based heterogeneous catalysts.…”

Section: ■ Introductionmentioning

confidence: 99%

“…In recent decades, several heterogeneous palladium catalytic systems have been developed and proposed with the intention of not only simplifying the separation of the catalyst from the reaction mixtures but also realizing its effective reuse to minimize the loss of extremely precious palladium. Among the heterogeneous Pd-based catalysts used in the Sonogashira cross-coupling, Pd/C is an effective and preferred choice due to its thermal stability, low cost, and large availability. , …”

Section: Introductionmentioning

confidence: 99%

Biomass Waste-Derived Pd–PiNe Catalyst for the Continuous-Flow Copper-Free Sonogashira Reaction in a CPME–Water Azeotropic Mixture

Ferlin

Valentini

Sciosci

et al. 2021

ACS Sustainable Chem. Eng.

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Herein, we report on the development of a waste minimization/valorization methodology applied to the representative benchmark Sonogashira cross-coupling reaction performed in a continuous-flow reactor, featuring a continuous-flow downstream membrane organic/aqueous separator to recover medium and products with minimal waste. The protocol is based on the use of a biomass waste-derived heterogeneous Pd-based catalyst, which is obtained from the valorization of urban-waste pine needles (PiNe). In a circular economy approach, the PiNe biomass has been proven to be capable of producing an effective active carbon support for Pd nanoparticle immobilization. In addition, the catalyst has been utilized in an azeotropic mixture formed by industrial wastederived cyclopentyl methyl ether (CPME) and water. Thanks to this combination and with the adoption of flow conditions, high yields of final target products could be accessed with high stability and durability of the catalyst. Final isolation of the products has been realized by setting an in-line liquid−liquid separator in flow, which has also allowed CPME recovery with a significant reduction of the waste generated. The protocol has been applied to the representative preparation of eniluracil, a GSK API.

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Synthesis of pyrrolo-pyrrolo-pyrazines via the Pd/C-catalyzed cyclization of N-propargyl pyrrolinyl-pyrrole derivatives

Cited by 9 publications

References 28 publications

Recent Advances in Functionalization of Pyrroles and their Translational Potential

Recent Advances in Functionalization of Pyrroles and their Translational Potential

Design of 1‐(2‐pyrrolidinone)‐butane‐1,3‐dione derivatives and acetoxylation of these compound's methylene via hypervalent iodine (III)

Biomass Waste-Derived Pd–PiNe Catalyst for the Continuous-Flow Copper-Free Sonogashira Reaction in a CPME–Water Azeotropic Mixture

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