Replacement of aryl by alkyl in 1-substituted 1H-1,2,3-triazole-4-carbaldehydes

L'abbé, G.; Bruynseels, Maria

doi:10.1039/p19900001492

Cited by 11 publications

(3 citation statements)

References 12 publications

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“…Based on this observation, it is expected that azides with electron-deficient aryl groups will be the most suitable substrates for the synthesis of 1-aryl-4-formyl-1,2,3-triazoles from 3-dimethylaminoacrolein. With a metal-free protocol for the multigram scale preparation of FNPT 1a in hand, we wanted to further explore the previously reported reaction with primary amines 2 [1,20,[32][33][34], i.e., imine formation, Cornforth rearrangement, and hydrolysis, in a single step (Table 1). The study was initiated with hexylamine.…”

Section: Resultsmentioning

confidence: 99%

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1-(4-Nitrophenyl)-1H-1,2,3-Triazole-4-carbaldehyde: Scalable Synthesis and Its Use in the Preparation of 1-Alkyl-4-Formyl-1,2,3-triazoles

et al. 2021

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1,2,3-Triazole-4-carbaldehydes are useful synthetic intermediates which may play an important role in the discovery of novel applications of the 1,2,3-triazole moiety. In this work, a one-step multigram scale synthesis of 4-formyl-1-(4-nitrophenyl)-1H-1,2,3-triazole (FNPT) as a preferred reagent for the synthesis of 1-alkyl-4-formyltriazoles is described, making use of the commercially available 3-dimethylaminoacrolein and 4-nitrophenyl azide. Next, the earlier reported reaction of FNPT with alkylamines is further explored, and for hexylamine, the one-pot sequential cycloaddition and Cornforth rearrangement is demonstrated. In addition, a useful protocol for the in situ diazotization of 4-nitroaniline is provided. This facilitated the complete hydrolysis of rearranged 4-iminomethyl-1,2,3-triazoles and allowed for the recycling of 4-nitrophenyl azide.

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Section: Resultsmentioning

confidence: 99%

“…With a metal-free protocol for the multigram scale preparation of FNPT 1a in hand, we wanted to further explore the previously reported reaction with primary amines 2 [1,20,[32][33][34], i.e., imine formation, Cornforth rearrangement, and hydrolysis, in a single step (Table 1). The study was initiated with hexylamine.…”

Section: Resultsmentioning

confidence: 99%

1-(4-Nitrophenyl)-1H-1,2,3-Triazole-4-carbaldehyde: Scalable Synthesis and Its Use in the Preparation of 1-Alkyl-4-Formyl-1,2,3-triazoles

et al. 2021

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“…From a more practical point of view, the importance of studying the reproducible nature and scan rate dependence of the hysteresis loop and high-temperature SCO with sufficient thermal stability has recently been pointed out in order to define the limiting characteristics of SCO materials [33,[35][36][37][38][39]. Recently, we have focused on SCO molecules with 1-R-1H-1,2,3-triazole-containing Schiff-base (1-R-1H-1,2,3-triazolimine; R = Me and Ph) ligands since the ligand system can easily modify its structure with the choice of a substituent R of a precursor, 1-R-1H-1,2,3-triazole-4-carbaldehyde, and another amino precursor by simple click reaction [40][41][42], Schiff-base reaction [43] and replacement of R using the method reported by L'abbé and coworkers [44,45]. The iron(II) complexes with multidentate 1-R-1H-1,2,3-triazolimine ligand show a variety of SCO properties such as gradual, abrupt, and two-step transition with (or without) hysteresis in a wide temperature range (around RT, below RT and above RT over ca.…”

Section: Introductionmentioning

confidence: 99%

High-Temperature Wide Thermal Hysteresis of an Iron(II) Dinuclear Double Helicate

Hora

Hagiwara

2017

Inorganics

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Abstract:Two new dinuclear iron(II) complexes (1·PF 6 and 1·AsF 6 ) of the general formula [Fe II 2 (L2 C3 ) 2 ](X) 4 ·nH 2 O·mMeCN (X = PF 6 , n = m = 1.5 for 1·PF 6 and X = AsF 6 , n = 3, m = 1 for 1·AsF 6 ) have been prepared and structurally characterized, where L2 C3 is a bis-1,2,3-triazolimine type Schiff-baseSingle crystal X-ray structure analyses revealed that 1·PF 6 and 1·AsF 6 are isostructural. The complex-cation [Fe II 2 (L2 C3 ) 2 ] 4+ of both has the same dinuclear double helicate architecture, in which each iron(II) center has an N6 octahedral coordination environment. Neighboring helicates are connected by intermolecular π-π interactions to give a chiral one-dimensional (1D) structure, and cationic 1D chains with the opposite chirality exist in the crystal lattice to give a heterochiral crystal. Magnetic and differential scanning calorimetry (DSC) studies were performed only for 1·AsF 6 , since the thermal stability in a high-temperature spin crossover (SCO) region of 1·PF 6 is poorer than that of 1·AsF 6 . 1·AsF 6 shows an unsymmetrical hysteretic SCO between the low-spin-low-spin (LS-LS) and high-spin-high-spin (HS-HS) states at above room temperature. The critical temperatures of warming (T c ↑) and cooling (T c ↓) modes in the abrupt spin transition area are 485 and 401 K, respectively, indicating the occurrence of 84 K-wide thermal hysteresis in the first thermal cycle.

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Réactions des Méthylazide et Phénylazide Avec Quelques Alcynes et Oléfines α‐Nitrées. Synthèse Régiospécifique des 1,2,3 Triazoles

Piet¹,

Hétet²,

Cailleux³

et al. 1996

Bulletin des Soc Chimique

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The reactions of alkynes and a-nitro-olefines with methylazide and phenylazide was studied. In contrast to known reactions with alkynes which are non-regioselective, methylazide and phenylazide react regiospecifically with a-nitro-olefines and give only one type of triazole after elimination of HN02. These reactions are very useful synthetic approaches to 1,2,3 triazoles.Les 1,2,3 triazoles ont fait I'objet de nombreux

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Replacement of aryl by alkyl in 1-substituted 1H-1,2,3-triazole-4-carbaldehydes

Cited by 11 publications

References 12 publications

1-(4-Nitrophenyl)-1H-1,2,3-Triazole-4-carbaldehyde: Scalable Synthesis and Its Use in the Preparation of 1-Alkyl-4-Formyl-1,2,3-triazoles

1-(4-Nitrophenyl)-1H-1,2,3-Triazole-4-carbaldehyde: Scalable Synthesis and Its Use in the Preparation of 1-Alkyl-4-Formyl-1,2,3-triazoles

High-Temperature Wide Thermal Hysteresis of an Iron(II) Dinuclear Double Helicate

Réactions des Méthylazide et Phénylazide Avec Quelques Alcynes et Oléfines α‐Nitrées. Synthèse Régiospécifique des 1,2,3 Triazoles

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