Fe-catalyzed synthesis of flunarizine and its (Z)-isomer

Shakhmaev, R. N.; Сунагатуллина, А. Ш.; Зорин, В. В.

doi:10.1134/s107036321608034x

Cited by 10 publications

(5 citation statements)

References 16 publications

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“…In this regard, recent studies by Shakhmaev and co‐workers demonstrated the effect of substoichiometric amounts of NMP on C(sp 2 )−C(sp 2 ) allyl–aryl cross‐couplings using Fe(acac) 3 (1 mol %; Scheme ) . This method was applied to short syntheses of allylamine pharmaceuticals, such as naftifine (antifungal), cinnarizine (antihistamine), and flunarizine (calcium antagonist) . It is likely that the amino group of the substrate acts as a ligand to iron in these couplings …”

Section: Development Of Sustainable Methodsmentioning

confidence: 99%

Iron‐Catalyzed Cross‐Couplings in the Synthesis of Pharmaceuticals: In Pursuit of Sustainability

2018

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The scarcity of precious metals has led to the development of sustainable strategies for metal-catalyzed cross-coupling reactions. The establishment of new catalytic methods using iron is attractive owing to the low cost, abundance, ready availability, and very low toxicity of iron. In the last few years, sustainable methods for iron-catalyzed cross-couplings have entered the critical area of pharmaceutical research. Most notably, iron is one of the very few metals that have been successfully field-tested as highly effective base-metal catalysts in practical, kilogram-scale industrial cross-couplings. In this Minireview, we critically discuss the strategic benefits of using iron catalysts as green and sustainable alternatives to precious metals in cross-coupling applications for the synthesis of pharmaceuticals. The Minireview provides an essential introduction to the fundamental aspects of practical iron catalysis, highlights areas for improvement, and identifies new fields to be explored.

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Section: Development Of Sustainable Methodsmentioning

confidence: 99%

Iron‐Catalyzed Cross‐Couplings in the Synthesis of Pharmaceuticals: In Pursuit of Sustainability

2018

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“…[41] In dieser Hinsicht demonstrieren aktuelle Studien von Shakhmaev und Mitarbeitern den Einfluss substçchiometrischer Mengen von NMP auf C(sp 2 )-C(sp 2 )-Allyl-Aryl-Kreuzkupplungen mit Fe(acac) 3 (1 Mol-%; Schema 19). [65] Die Methode wurde in kurzen Synthesen von Allylamin-Pharmazeutika eingesetzt, wie z. B. Naftifin (Antimykotikum), […”

Section: Die Entwicklung Nachhaltiger Methodenunclassified

Eisenkatalysierte Kreuzkupplungen in der Synthese von Pharmazeutika: Streben nach Nachhaltigkeit

Piontek¹,

Bisz²,

Szostak

2018

Angewandte Chemie

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Der Mangel an Edelmetallen hat eine Suche nach nachhaltigen Strategien für metallkatalysierte Kreuzkupplungen ausgelöst. Die Entwicklung neuer Katalysemethoden unter Verwendung von Eisen ist wegen der geringen Kosten, leichten Verfügbarkeit und sehr geringen Toxizität von Eisen hoch attraktiv. In den letzten Jahren haben nachhaltige Methoden für eisenkatalysierte Kreuzkupplungen den kritischen Bereich der pharmazeutischen Forschung erreicht. Insbesondere ist Eisen eines der sehr wenigen unedlen Metalle, deren praktischer Einsatz in industriellen Kreuzkupplungen im Kilogrammmaßstab erfolgreich erprobt wurde. In diesem Kurzaufsatz wollen wir die strategischen Vorteile der Verwendung von Eisenkatalysatoren als umweltfreundliche und nachhaltige Alternative zu Edelmetallen in Kreuzkupplungen für die Synthese von Pharmazeutika kritisch beleuchten. Wir bieten eine Einführung in die grundlegenden Aspekte der Eisenkatalyse, heben Bereiche mit Verbesserungspotenzial hervor und zeigen neue Richtungen auf, die in Zukunft erforscht werden sollten.

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“…Shakhmaev et al 174 proposed the effect of substoichiometric amounts of NMP on C(sp 2 )−C(sp 2 ) allyl−aryl cross-coupling using 1 mol % of Fe(acac) 3 . The suggested approach can provide a short synthesis route of allylamine pharmaceuticals such as cinnarizine, naftifine, flunarizine, etc.…”

Section: Metal-catalyzed Cross-couplingmentioning

confidence: 99%

Green Chemistry in the Synthesis of Pharmaceuticals

et al. 2021

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The principles of green chemistry (GC) can be comprehensively implemented in green synthesis of pharmaceuticals by choosing no solvents or green solvents (preferably water), alternative reaction media, and consideration of one-pot synthesis, multicomponent reactions (MCRs), continuous processing, and process intensification approaches for atom economy and final waste reduction. The GC's execution in green synthesis can be performed using a holistic design of the active pharmaceutical ingredient's (API) life cycle, minimizing hazards and pollution, and capitalizing the resource efficiency in the synthesis technique. Thus, the presented review accounts for the comprehensive exploration of GC's principles and metrics, an appropriate implication of those ideas in each step of the reaction schemes, from raw material to an intermediate to the final product's synthesis, and the final execution of the synthesis into scalable industry-based production. For real-life examples, we have discussed the synthesis of a series of established generic pharmaceuticals, starting with the raw materials, and the intermediates of the corresponding pharmaceuticals. Researchers and industries have thoughtfully instigated a green synthesis process to control the atom economy and waste reduction to protect the environment. We have extensively discussed significant reactions relevant for green synthesis, one-pot cascade synthesis, MCRs, continuous processing, and process intensification, which may contribute to the future of green and sustainable synthesis of APIs. CONTENTS1. Introduction 3638 2. Green Chemistry (GC) 3639 2.1. Definition 3639 2.2. The Principles of GC 3641 2.3. The Metrics of GC 3641 2.3.1. Standardization of the E Factor Concept 3641 2.3.2. Baran's Process Ideality Metric 3641 2.3.3. Identification of Process Complexity 3641 2.3.4. The Green Aspiration Level Concept 3642 2.3.5. Innovation Green Aspiration Level (iGAL) 3642 3. The Choice of Solvents in the Green Synthesis of APIs 3642 4. The Reaction with Green Solvents 3643 4.1. The No-Solvent Process 3644 4.

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Fe-catalyzed synthesis of flunarizine and its (Z)-isomer

Cited by 10 publications

References 16 publications

Iron‐Catalyzed Cross‐Couplings in the Synthesis of Pharmaceuticals: In Pursuit of Sustainability

Iron‐Catalyzed Cross‐Couplings in the Synthesis of Pharmaceuticals: In Pursuit of Sustainability

Eisenkatalysierte Kreuzkupplungen in der Synthese von Pharmazeutika: Streben nach Nachhaltigkeit

Green Chemistry in the Synthesis of Pharmaceuticals

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