Photooxygenation of azidoalkyl furans has revealed both a novel triazole formation method and a unique endoperoxide rearrangement. The key step of this method is a 3 + 2 cycloaddion of the azide to the endoperoxide intermediate. The reduction of the peroxide bond and two subsequent C-C bond cleavages provide a triazole having a newly formed carboxylic acid functionality. The reactions are clean...

The title compound, C(13)H(11)N(3)O(3)S, was synthesized from 1H-1,2,4-triazole-5-thiol in a one pot reaction. The fused thia-zolo[3,2-b][1,2,4]triazole system is essentially coplanar with the benzene ring: they enclose an inter-planar angle of 1.37 (13)°. The olefinic double bond is in a Z conformation. In the crystal, C-H⋯N hydrogen bonds link the mol-ecules into double layers parallel to the...

The natural amide bond found in all biotinylated proteins has been replaced with a triazole through CuAAC reaction of an alkynyl biotin derivative. The resultant triazole-linked adducts are shown to be highly resistant to the ubiquitous hydrolytic enzyme biotinidase and to bind avidin with dissociation constants in the low pM range. Application of this strategy to the production of a series of ...

A small library of 1,5-triazole derivatives linking a diaminocyclopentadiol and aromatic ketones has been prepared and screened using NMR and fluorescent techniques against tRNA(Lys)(3), the HIV reverse transcription primer. The comparison of their binding properties to those of their 1,4-triazole isomers, previously discovered in a fragment-based approach, outlines the influence of the linker ...

In the title compound, C(20)H(16)N(4)O(2), the benzene rings of the 2-hydroxy-phenyl and 4-methoxy-lphenyl groups form dihedral angles of 64.02 (8) and 77.39 (7)°, respectively, with the mean plane of the triazole ring. The dihedral angle between the triazole ring mean plane and the pyridyl ring is 9.61 (8)°. In the crystal, inter-molecular N-H⋯O hydrogen bonds link the mol-ecules into zigzag c...

Under neutral conditions the reactions between 4-amino-1,2,4-triazole and cyano-substituted benzaldehyde derivatives yield stable hemiaminals. Addition of small amounts of acid catalyst promotes further step of dehydration resulting in formation of Schiff bases. Four new hemiaminals and the corresponding imines have been obtained. The molecular stability of the hemiaminal intermediates results ...

In the title compound, C(14)H(10)N(6)O(2)S, the dihedral angle between the pyridine and triazole rings is 3.21 (10)°. The mol-ecule is significantly twisted about the N(t)-N(b) (t = triazole and b = benzyl-idene) bond [C-N(t)-N(b)=C = 151.64 (17)°]. In the crystal, mol-ecules are linked by weak N-H⋯N hydrogen bonds, generating C(8) chains propagating in [10[Formula: see text]].

The title compound, C(8)H(8)N(6)O, was obtained by the reaction of 3,5-diamino-1,2,4-triazole with ethyl 2-picolinate in a glass oven. The dihedral angles formed between the plane of the amide group and the pyridine and triazole rings are 11.8 (3) and 5.8 (3)°, respectively. In the crystal, an extensive system of classical N-H⋯N and N-H⋯O hydrogen bonds generate an infinite three-dimensional ne...

In the title mol-ecule, C(30)H(23)N(5)O(3)S, the 1,2,4-triazole ring is approximately planar (r.m.s. deviation = 0.006 Å), and forms dihedral angles of 66.0 (2), 65.1 (2), 30.1 (2) and 28.1 (2)° with the four phenyl rings. The phenyl ring of the benzyl group directly attached to the triazole ring is almost perpendicular to the nitro-phenyl ring, making a dihedral angle of 84.9 (2)°.

Since the discovery of Cu(I)-catalysed click chemistry, the field of peptidomimetics has expanded to include 1,4-connected 1,2,3-triazoles as useful peptide bond isosteres. Here, we report the synthesis of triazole-containing analogues of the naturally occurring tyrosinase inhibitor cyclo-[Pro-Val-Pro-Tyr] and show that the analogues retain enzyme inhibitory activity, demonstrating the effectiv...