Direct synthesis of triazines from alcohols and amidines using supported Pt nanoparticle catalysts <i>via</i> the acceptorless dehydrogenative methodology

Poly, Sharmin Sultana; Hashiguchi, Yasuyuki; Nakamura, Isao; Fujitani, Tadahiro; Siddiki, S. M. A. Hakim

doi:10.1039/d2cy00426g

Cited by 5 publications

(3 citation statements)

References 40 publications

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“…Poly and colleagues synthesised triazines (122) using aliphatic/aromatic amidines (120) and aliphatic/benzylic primary alcohols (121) catalysed by recyclable (six times) alumina-supported PtNPs (Pt/Al 2 O 3 ) through cyclocondensation and acceptor-less sequential dehydrogenation (Scheme 34). 87 The catalysts were prepared from alumina and Pt(NH 3 ) 2 (NO 3 ) 2 and were characterised by DF-STEM, DF-STEM-EDS, DF-STEM-EELS mapping, etc.…”

Section: Ptnpsmentioning

confidence: 99%

Synthesis of Nitrogen- and Oxygen-Containing Heterocycles Catalysed by Metal Nanoparticles Reported in 2022

Dhameliya,

Shah,

Shah

et al. 2024

Synlett

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The versatility of aza- and oxa-heterocyclic compounds has garnered significant attention in recent times. A large number of currently approved pharmaceutical products include nitrogen- and oxygen-containing heterocycles. Recent nanotechnological developments have propelled an upsurge in the applications of nanocatalysis for heterocyclic synthesis. Metal nanoparticles (MNPs) have emerged as promising catalysts for the synthesis of aza- and oxa-heterocycles owing to their unique physicochemical properties. Various MNPs including gold, silver, nickel and palladium have been evaluated for their catalytic activities in different reaction types, including cyclisation, coupling, hydrogenation and oxidative transformations. The MNPs have exhibited remarkable catalytic efficiency when utilised under optimal conditions. These catalysts have showcased high reusability and recyclability, yielding satisfactory amounts of the desired heterocyclic compound. The present work provides a detailed overview of recent advances in the area of MNP-assisted synthetic construction of aza- and oxa-heterocycles, published during the previous calendar year, 2022. The review serves as a valuable resource and also paves the way for future investigations in the development of novel catalytic strategies for heterocycle synthesis.1 Introduction2 Nanocatalysis3 Aza- and Oxa-Heterocycle Synthesis Catalysed by MNPs3.1 AuNPs3.2 CuNPs3.3 CoNPs3.4 FeNPs3.5 NiNPs3.6 PdNPs3.7 PtNPs3.8 SiNPs3.9 ZnNPs3.10 Bimetallic NPs3.11 Other MNPs4 Summary and Outlook

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Section: Ptnpsmentioning

confidence: 99%

Synthesis of Nitrogen- and Oxygen-Containing Heterocycles Catalysed by Metal Nanoparticles Reported in 2022

Dhameliya,

Shah,

Shah

et al. 2024

Synlett

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“…At the end of the reaction, the desired products were obtained in moderate to good yields up to 91%. In another example, Poly et al demonstrated the use of primary alcohols and amidines as molecular building blocks for triazine synthesis by applying alumina-supported Pt (Pt/Al 2 O 3 ) nanoparticle catalyst ( Scheme 12 b) [ 126 ]. The acceptorless dehydrogenative coupling reaction was carried out in one pot with high atom economy and good yields of up to 93%.…”

Section: Six-membered Ringsmentioning

confidence: 99%

Green Synthesis of Aromatic Nitrogen-Containing Heterocycles by Catalytic and Non-Traditional Activation Methods

2023

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Recent advances in the environmentally benign synthesis of aromatic N-heterocycles are reviewed, focusing primarily on the application of catalytic methods and non-traditional activation. This account features two main parts: the preparation of single ring N-heterocycles, and their condensed analogs. Both groups include compounds with one, two and more N-atoms. Due to the large number of protocols, this account focuses on providing representative examples to feature the available methods.

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“…[21] The known methods for the preparation of guanamines are diverse as can be illustrated by synthetic approaches to 6phenyl-1,3,5-triazine-2,4-diamine (6 e), which is also known as benzoguanamine (Scheme 1). These approaches include the Suzuki coupling of 6-chloro-1,3,5-triazine-2,4-diamine (7) with phenylboronic acid (8), [22] ring rearrangement of 5-phenyl-1,2,4triazine (9) upon the treatment with potassium amide (10), [23] the reaction of guanidine (11) and benzyl alcohol (12) under the alumina-supported Pt catalysis, [24] the cyclocondensation of N-cyanobenzamidine (13) and guanidine (11), [25] and the reaction of N-benzoylcyanoguanidine (14) with cyanamide (15). [26] However, the most practical methods with the greatest atom economy [27] utilize the base-catalyzed reaction of cyanoguanidine (16) with benzonitrile (17 e) for the synthesis of benzoguanamine (6 e).…”

Section: Introductionmentioning

confidence: 99%

Polyethylene Glycol as a Green Medium for the Microwave‐Assisted Synthesis of Guanamines

Lim

Dolzhenko

2023

ChemistrySelect

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The hazardous, toxic, and flammable solvents, methyl and ethyl cellosolves (2‐methoxy‐ and 2‐ethoxyethanols), are typically used as media for the synthesis of guanamines (1,3,5‐triazine‐2,4‐diamines). We found that these problematic solvents can be efficiently replaced by a green alternative, polyethylene glycol 400 (PEG 400). The reaction efficiency in PEG 400 media was further improved by applying focused microwave irradiation. The method scope is illustrated by the preparation of twenty diverse 1,3,5‐triazine‐2,4‐diamines.

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Direct synthesis of triazines from alcohols and amidines using supported Pt nanoparticle catalysts via the acceptorless dehydrogenative methodology

Abstract: We report a cost-effective, green, and acceptorless dehydrogenative one-pot synthesis of triazine from primary alcohols and amidines using alumina-supported Pt nanoparticle catalyst (Pt/Al2O3). This reaction proceeds with high atom efficiency...

Cited by 5 publications

References 40 publications

Synthesis of Nitrogen- and Oxygen-Containing Heterocycles Catalysed by Metal Nanoparticles Reported in 2022

Synthesis of Nitrogen- and Oxygen-Containing Heterocycles Catalysed by Metal Nanoparticles Reported in 2022

Green Synthesis of Aromatic Nitrogen-Containing Heterocycles by Catalytic and Non-Traditional Activation Methods

Polyethylene Glycol as a Green Medium for the Microwave‐Assisted Synthesis of Guanamines

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