Facile Synthesis of 1,2,4-Triazoles via a Copper-Catalyzed Tandem Addition−Oxidative Cyclization

Ueda, Satoshi; Nagasawa, Hideko

doi:10.1021/ja905056z

Cited by 270 publications

(121 citation statements)

References 21 publications

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“…Amidine hydrochlorides transformed into free amidines in the presence of base (Cs 2 CO 3 ), and intermolecular nucleophilic attack of amino in one amidine to carbon in another one leads to intermediate I. Treatment of I with copper in the presence of O 2 provides Cu(III) complex II (the similar metal complexes have been reported in the previous literature 15 ), and reductive elimination of II affords the target product (2) 14 leaving Cu(I) complex III. Further, reaction of III with I regenerates II, and the target product 2 16 continuously is provided in the catalytic cycle.…”

Section: The Synthesized N-[amino(m-tolyl)methylene]-4-methyl-mentioning

confidence: 74%

Copper-Catalyzed Synthesis of 1,2,4-Triazoles via Sequential Coupling and Aerobic Oxidative Dehydrogenation of Amidines

Jiang

2012

Synlett

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A convenient, efficient, and practical copper-catalyzed one-pot method for the synthesis of 1,2,4-triazoles has been developed via reactions of amidines. The procedure underwent sequential base-promoted intermolecular coupling (nucleophilic substitution) between two amidines and intramolecular aerobic oxidative dehydrogenation, and the inexpensive, convenient, and efficient method for the synthesis of 1,2,4-triazoles will attract much attention in academic and industrial research.

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Section: The Synthesized N-[amino(m-tolyl)methylene]-4-methyl-mentioning

confidence: 74%

Copper-Catalyzed Synthesis of 1,2,4-Triazoles via Sequential Coupling and Aerobic Oxidative Dehydrogenation of Amidines

Jiang

2012

Synlett

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“…Further studies of substituents effects demonstrated that the electron withdrawing groups like halogens and trifluoromethyl group on benzene ring gave the corresponding triazoles with good yields, while benzonitrile was substituted by methoxy group, the transformation efficiency was quite low to 55%. Acetonitrile could also be employed instead of benzonitrile to prepare triazoles in similar yield (52%) [176].…”

Section: Cyclizations Of Other Compoundsmentioning

confidence: 99%

Current Developments in the Syntheses of 1,2,4-Triazole Compounds

Zhang¹,

Damu²,

Cai³

et al. 2014

COC

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Heterocyclic 1,2,4-triazole derivatives possess unusually spacious potentiality as medicinal agents, agricultural chemicals, functional materials, ionic liquids, supramolecular catalysts as well as artificial enzymes and receptors for supramolecular recognition and biomimetic catalysis, and their various researches and developments have been being a quite rapidly developing and active highlight topic with an infinite space. Numerous efforts have been directed toward various types of possible applications of 1,2,4-triazole-based compounds and a lot of important progress has been made, especially their preparations have attracted increasing attention. This review systematically summarized the recent advances in the syntheses of 1,2,4-triazole derivatives, including: (1) Cyclizations to form triazole ring; (2) Transformations of heterocyclic compounds to construct triazole ring; (3) Substitutions on 1,2,4-triazole ring; (4) Structural modifications in side chains of 1,2,4-triazole ring. It was hoped that this review would be helpful for the design and development of highly efficient preparation of 1,2,4-triazole derivatives with various sorts and varieties of extensively potential applications in medicine, agriculture, chemistry, materials, supramolecular sciences and so on.

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“…Buchwald postulierte drei mçgliche Mechanismen für die oxidative Anellierung, die alle auf der Koordination des anhängenden Amidins zum Cu-Zentrum beruhen (Schema 31). Weg A beschreibt einen [91] Aus mechanistischer Sicht wird angenommen, dass die Reaktion über die Addition der 2-Aminogruppe an das Nitril verläuft und ein N-2-Pyridylamidin bildet, das dann eine kupferkatalysierte oxidative N-N-Kupplung eingeht. Die oxidative Cyclisierung eines vorab gebildeten Amidins verläuft ohne Zink problemlos, was andeutet, dass ZnI 2 lediglich an der Bildung des Amidins beteiligt ist.…”

Section: C-h-oxidationen Nach Art Metallorganischer Reaktionenunclassified

Kupferkatalysierte aerobe oxidative C‐H‐Funktionalisierungen: Trends und Erkenntnisse zum Mechanismus

2011

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Die selektive Oxidation von C‐H‐Bindungen und der Einsatz von O2 als stöchiometrisches Oxidationsmittel stellen zwei wesentliche Herausforderungen in der organischen Chemie dar. Kupfer(II) ist ein vielseitiges Oxidationsmittel für verschiedene oxidative Kupplungen, die durch Einelektronen‐Transfer (SET) von elektronenreichen organischen Molekülen ausgelöst werden. Viele dieser Reaktionen können mit Kupfer katalytisch durchgeführt werden, wenn molekularer Sauerstoff als Oxidationsmittel eingesetzt wird, um den aktiven Kupfer(II)‐Katalysator zu regenerieren. Daneben wurden auch zahlreiche neue Cu‐katalysierte C‐H‐Oxidationen mit elektronenarmen Substraten beschrieben, von denen ein SET zum Kupfer(II) unwahrscheinlich scheint. In einigen dieser Fälle konnte die Beteiligung von Organokupfer(III)‐Intermediaten im Reaktionsmechanismus nachgewiesen werden. Metallorganische C‐H‐Oxidationen dieser Art eröffnen neue bedeutende Möglichkeiten für das Gebiet der Cu‐katalysierten aeroben Oxidationen.

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Facile Synthesis of 1,2,4-Triazoles via a Copper-Catalyzed Tandem Addition−Oxidative Cyclization

Cited by 270 publications

References 21 publications

Copper-Catalyzed Synthesis of 1,2,4-Triazoles via Sequential Coupling and Aerobic Oxidative Dehydrogenation of Amidines

Copper-Catalyzed Synthesis of 1,2,4-Triazoles via Sequential Coupling and Aerobic Oxidative Dehydrogenation of Amidines

Current Developments in the Syntheses of 1,2,4-Triazole Compounds

Kupferkatalysierte aerobe oxidative C‐H‐Funktionalisierungen: Trends und Erkenntnisse zum Mechanismus

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