Synthesis of 4-aryl-5,5-dimethyl-5H-1,2,3-triazoles and 4-aryl-3-cyano-5,5-dimethyl Δ1-pyrazolines by cycloaddition of 2-diazopropane with iminoethers and propenenitriles

Toumi, Baya; Harizi, Abdallah

doi:10.1016/j.tetlet.2006.06.161

Cited by 8 publications

(1 citation statement)

References 14 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…2 Among the heterocyclic compounds that have a triazolic core, we highlight 1-(2,6-difluorbenzyl)-1H-1,2,3-triazol-4-yl carboxamide (rufinamide), which is a drug that has anticonvulsant activity, especially when used in combination with other antiepileptic medications for the treatment of several forms of the childhood epilepsy known as Lennox-Gastaut syndrome. 3 Epilepsy is a neurological disorder that is characterized by recurrent seizures.…”

Section: Introductionmentioning

confidence: 99%

New solventless and metal-free synthesis of the antiepileptic drug 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxamide (Rufinamide) and analogues

Bonacorso

Moraes

Luz

et al. 2015

Tetrahedron Letters

View full text Add to dashboard Cite

Section: Introductionmentioning

confidence: 99%

New solventless and metal-free synthesis of the antiepileptic drug 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxamide (Rufinamide) and analogues

Bonacorso

Moraes

Luz

et al. 2015

Tetrahedron Letters

View full text Add to dashboard Cite

Synthesis of 4‐Aryl‐5,5‐dimethyl‐5H‐1,2,3‐triazoles and 4‐Aryl‐3‐cyano‐5,5‐dimethyl Δ¹‐Pyrazolines by Cycloaddition of 2‐Diazopropane with Iminoethers and Propenenitriles.

Toumi¹,

Harizi²

2006

ChemInform

View full text Add to dashboard Cite

Propenenitriles. -1,3-Dipolar cycloaddition of 2-diazopropane (II) to iminoethers (I) and 3-arylpropene nitriles (V) and (VII) occurs regioselectively leading to the synthesis of triazoles (IV) and ∆ 1 -pyrazolines (VI) and (VIII), respectively. -(TOUMI, B.; HARIZI*, A.; Tetrahedron Lett. 47 (2006) 37, 6685-6687; Dep. Sci. Fondament., Inst. Super. Technol. Med., 1006 Tunis, Tunisia; Eng.) -Mais 52-132

show abstract

1,3‐Dipolar Cycloaddition of Carbodiimides and Nitrilimines: Synthesis and Mechanistic Study of 5‐Amino‐1,2,4‐triazoles

2016

View full text Add to dashboard Cite

An effective 1,3‐dipolar cycloaddition was developed for the synthesis of 5‐amino‐1,2,4‐triazoles by reacting hydrazonoyl hydrochlorides (nitrilimines) with carbodiimides in the presence of triethylamine as a base. Both symmetric and asymmetric carbodiimides are compatible with this newly developed reaction; diphenyl carbodiimide is the one exception. Mechanistic studies indicate that alkyl and cycloalkyl moieties of the quaternary N+–R on the 1,2,4‐triazolic ring serve as potential leaving groups and can efficiently depart from the intermediate 4,5‐dihydro‐4‐alkyl‐5‐imino‐1,2,4‐triazole.

show abstract

Synthesis of 4-aryl-5,5-dimethyl-5H-1,2,3-triazoles and 4-aryl-3-cyano-5,5-dimethyl Δ1-pyrazolines by cycloaddition of 2-diazopropane with iminoethers and propenenitriles

Cited by 8 publications

References 14 publications

New solventless and metal-free synthesis of the antiepileptic drug 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxamide (Rufinamide) and analogues

New solventless and metal-free synthesis of the antiepileptic drug 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxamide (Rufinamide) and analogues

Synthesis of 4‐Aryl‐5,5‐dimethyl‐5H‐1,2,3‐triazoles and 4‐Aryl‐3‐cyano‐5,5‐dimethyl Δ¹‐Pyrazolines by Cycloaddition of 2‐Diazopropane with Iminoethers and Propenenitriles.

1,3‐Dipolar Cycloaddition of Carbodiimides and Nitrilimines: Synthesis and Mechanistic Study of 5‐Amino‐1,2,4‐triazoles

Contact Info

Product

Resources

About

Synthesis of 4-aryl-5,5-dimethyl-5H-1,2,3-triazoles and 4-aryl-3-cyano-5,5-dimethyl Δ1-pyrazolines by cycloaddition of 2-diazopropane with iminoethers and propenenitriles

Cited by 8 publications

References 14 publications

New solventless and metal-free synthesis of the antiepileptic drug 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxamide (Rufinamide) and analogues

New solventless and metal-free synthesis of the antiepileptic drug 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxamide (Rufinamide) and analogues