The reaction of 4,4-dichloro-1,2-diazabuta-1,3-dienes with sodium azide has been studied and found to provide straightforward access to extremely rare 1,1-bisazides. It was demonstrated that these highly unstable compounds are prone to eliminate the N 2 molecule to cyclize into 4-azido-1,2,3-triazoles bearing two aryl (heteroaryl) groups at positions 2 and 5. The formation of bisazides was confirmed by their trapping with cyclooctyne and B3LYP calculations. Most likely, the elimination of nitrogen to form an intermediate nitrene is facilitated by the aza group via anchimeric-like participation. The reaction was found to be very general for the highly efficient synthesis of various 4-azidotriazoles. It was demonstrated that these heterocycles are highly attractive building blocks for subsequent preparation of 1,2,3-triazole-derived compounds.
Efficient synthesis of 2,5-diaryl substituted 4-azido-1,2,3-triazoles by the reaction of sodium azide with dichlorosubstituted diazadienes was demonstrated. The optical properties of the prepared azidotriazoles were studied to reveal a luminescence maximum in the 360–420 nm region. To improve the luminescence quantum yields a family of 4-azido-1,2,3-triazoles bearing ortho-propargyloxy substituents in the 5 position was prepared. Subsequent intramolecular thermal cyclization permits to construct additional triazole fragment and obtain unique benzoxazocine derivatives condensed with two triazole rings. This new family of condensed heterocycles has a flattened heterocyclic system structure to provide more conjugation of the 5-aryl fragment with the triazole core. As a result, a new type of UV/“blue light-emitting” materials with better photophysical properties was obtained.
Thus, we have shown that complexation of the IBU with AG results in its bioavailability increase, reduction of the effective dose and should decrease toxic side effects.
An efficient synthesis of 2-pyridine derived 4-azido-1,2,3-triazoles 2 was elaborated using the corresponding dichlorodiazadienes 1 as precursors. The reaction of diazadienes 1 with sodium azide permits preparation of target triazoles...
An efficient three-step
synthesis of a new heterocyclic system is described wherein the 2H-bis([1,2,3]triazolo)[5,1-a:4′,5′-c]isoquinoline ring system is elaborated using a simple
synthetic strategy. The approach permits the preparation of target
compounds in high yields using readily available arylhydrazines and o-alkynylbenzaldehydes as starting materials. The photophysical
properties of the prepared heterocycles were studied to demonstrate
that the prepared compounds are attractive blue-emitting fluorophores,
exhibiting quantum yields up to 98% and Stokes shifts up to 67 nm.
A strong effect of the steric hindrance on the absorption and emission
spectra was revealed.
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