Facile synthesis of triimidazo[1,3,5]triazine derivatives

Verhé, Roland; Kimpe, Norbert De; Buyck, L. De; Schamp, N.; Declercq, Jean‐Paul; Germain, Gabriel; Meersche, M. Van

doi:10.1021/jo00420a031

Cited by 6 publications

(2 citation statements)

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“…De Kimpe et al 20 reported first steps in the preparation of triimidazo [1,3,5]triazine derivatives with the aim of combining three imidazole moieties in a polycyclic structure. More recently, a synthesis protocol in conjunction with single crystal structure determination of the basic cyclic triimidazole (triimidazo[1,2-a:1′,2′-c:1″,2″-e][1,3,5]triazine, hereafter referred to as TT) was described by Schubert et al 21 The molecular structure of the planar polycyclic ring system of TT is shown in Figure 1a.…”

Section: Introductionmentioning

confidence: 99%

Self-Assembly of N-Rich Triimidazoles on Ag(111): Mixing the Pleasures and Pains of Epitaxy and Strain

Ahsan,

Wang,

et al. 2023

J. Phys. Chem. C

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In the present report, homochiral hydrogen-bonded assemblies of heavily Ndoped (C 9 H 6 N 6 ) heterocyclic triimidazole (TT) molecules on an Ag(111) substrate were investigated using scanning tunneling microscopy (STM) and low energy electron diffraction (LEED) techniques. The planar and prochiral TT molecules, which exhibit a threefold rotation symmetry and lack mirror symmetry when assembled on the substrate, carry multiple hydrogen-bonding donor and acceptor functionalities, inevitably leading to the formation of hexameric two-dimensionally extended assemblies that can be either homo-(RR/SS) or heterochiral (RS). Experimental STM data showing well-ordered homochiral domains and experimental LEED data are consistent with simulations assuming the 21 21 × R19.1°o verlayer on the Ag(111) lattice. Importantly, we report the unexpected coincidence of spontaneous resolution with the condensation of neighboring islands in adjacent "Janus pairs". The islands are connected by a characteristic fault zone, an observation that we discuss in the context of the fairly symmetric molecule and its propensity to compromise and benefit from interisland bonding at the expense of lattice mismatches and strain in the defect zone. We relate this to the close to triangular shape and the substantial but weak bonding scheme beyond van der Waals (vdW) of the TT molecules, which is due to the three Ncontaining five-membered imidazole rings. Density functional theory (DFT) calculations show clear energetic differences between homochiral and heterochiral pairwise interactions, clearly supporting the experimental results.

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Section: Introductionmentioning

confidence: 99%

Self-Assembly of N-Rich Triimidazoles on Ag(111): Mixing the Pleasures and Pains of Epitaxy and Strain

Ahsan,

Wang,

et al. 2023

J. Phys. Chem. C

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“…Auch das bekannte Trimerisierungsprodukt 19 des Dihydroirnidazolons 15c, das durch thermische Methanolabspaltung aus 20c entsteht20), konnte bei der Photolyse von 12c nicht beobachtet werden.1-tert-Butylimidazolon 16 durfte durch Isomerisierung unter H-Wanderung aus dem 1,5-Dihydro-2H-imidazol-2-on 15a entstanden sein, das als Cyclisierungsprodukt einer primaren Photozwischenstufe zu betrachten ist. Auch das bekannte Trimerisierungsprodukt 19 des Dihydroirnidazolons 15c, das durch thermische Methanolabspaltung aus 20c entsteht20), konnte bei der Photolyse von 12c nicht beobachtet werden.1-tert-Butylimidazolon 16 durfte durch Isomerisierung unter H-Wanderung aus dem 1,5-Dihydro-2H-imidazol-2-on 15a entstanden sein, das als Cyclisierungsprodukt einer primaren Photozwischenstufe zu betrachten ist.…”

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Photochemische Stickstoff‐Eliminierung aus 1‐(1‐Alkenyl)‐4‐tert‐butyl‐1,4‐dihydro‐5H‐tetrazol‐5‐onen. Konkurrenz zwischen Methanol‐Addition und Cyclisierung einer dipolaren Zwischenstufe

Quast

Nahr

1984

Chem. Ber.

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Aus dem 5-Chlortetrazol 7 und dem Tetrazolon 9 werden auf verschiedenen Wegen die 4-terlButyl-1-vinyltetrazolone 12a -c sowie die Tetrazolone 13 und 14 hergestellt . Bei der 254-nm-Photolyse der 1-Vinyltetrazolone 12 erhalt man in Abhangigkeit von Struktur und Reaktionsbedingungen das Imidazolon 16, die 4-Methoxyimidazolidinone 20 und/oder die N-(l,2-Dimethoxyalky1)harnstoffe 22. Die Ergebnisse sprechen fur eine Konkurrenz zwischen Cyclisierung The 4-ferr-butyl-1-vinyltetrazolones 12a -c and the tetrazolones 13 and 14 are synthesized from the 5-chlorotetrazole 7 and the tetrazolone 9 ria several routes. Bis(benzonitri1e)palladium dichloride catalyses the 0 + N-Claisen rearrangement 8 + l l , the ally1 -+ vinyl rearrangements l l a -. 12b and l l b * 1212, as well as rhe equilibration 13 t 14. On 254 nm photolysis of the vinyltetrazolones 12 nitrogen is extruded and cyclic and/or acyclic products of primary photointermediates are formed: In [D3]acetonitrile as solvent, 77% of 1-fert-butylimidazolone 16 arises from 12a, while the tetrazolones 12b, c produce only complex mixtures. In methanol as solvent, the methanol adduct 2Oa (23%) of the intermediate imidazolone 15a and the acyclic N-(1,2-dimethoxyethy1)urea 22a (32%) are obtained besides 45% of 16. In contrast, from 12c in methanol the corresponding urea 22c is formed almost quantitatively as the only product. In

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2-Chloro-2-methylpropanalN-Isopropylimine

Kimpe

2001

Encyclopedia of Reagents for Organic Synthesis

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Facile synthesis of triimidazo[1,3,5]triazine derivatives

Cited by 6 publications

References 0 publications

Self-Assembly of N-Rich Triimidazoles on Ag(111): Mixing the Pleasures and Pains of Epitaxy and Strain

Self-Assembly of N-Rich Triimidazoles on Ag(111): Mixing the Pleasures and Pains of Epitaxy and Strain

Photochemische Stickstoff‐Eliminierung aus 1‐(1‐Alkenyl)‐4‐tert‐butyl‐1,4‐dihydro‐5H‐tetrazol‐5‐onen. Konkurrenz zwischen Methanol‐Addition und Cyclisierung einer dipolaren Zwischenstufe

2-Chloro-2-methylpropanalN-Isopropylimine

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