Synthesis of 2-amino-3-arylpropan-1-ols and 1-(2,3-diaminopropyl)-1,2,3-triazoles and evaluation of their antimalarial activity

• Matthias D’hooghe,
• Stéphanie Vandekerckhove,
• Karen Mollet,
• Karel Vervisch,
• Stijn Dekeukeleire,
• Liesbeth Lehoucq,
• Carmen Lategan,
• Peter J. Smith,
• Kelly Chibale and
• Norbert De Kimpe

Beilstein J. Org. Chem. 2011, 7, 1745–1752, doi:10.3762/bjoc.7.205

• approach is disclosed towards racemic aminopropanes 4 bearing a 1,2,3-triazole moiety, as structural analogues of the previously reported 1,2,4-triazoles 2 (Figure 1). Both classes of functionalized aminopropanes 3 and 4 were tested for their antiplasmodial activity. Results and Discussion Synthesis Within

• 1,2,3-triazole moiety instead. A powerful methodology towards the synthesis of functionalized 1,2,3-triazoles involves the Cu(I)-catalyzed azide-alkyne Huisgen cycloaddition (CuAAC) [33], which has gained major interest from the synthetic community due to its high efficiency and selectivity. Eligible

Highly efficient cyclosarin degradation mediated by a β-cyclodextrin derivative containing an oxime-derived substituent

• Michael Zengerle,
• Florian Brandhuber,
• Christian Schneider,
• Franz Worek,
• Georg Reiter and
• Stefan Kubik

Beilstein J. Org. Chem. 2011, 7, 1543–1554, doi:10.3762/bjoc.7.182

• with 2-formylpyridine oxime or 2-acetylpyridine oxime, unfortunately failed to produce the desired products. The cyclodextrin derivatives 2a–d contain 1,4-disubstituted 1,2,3-triazole moieties as the linking units. Accordingly, they were prepared by copper(I)-catalyzed azide–alkyne cycloaddition

Triazole–Au(I) complex as chemoselective catalyst in promoting propargyl ester rearrangements

• Dawei Wang,
• Yanwei Zhang,
• Rong Cai and
• Xiaodong Shi

Beilstein J. Org. Chem. 2011, 7, 1014–1020, doi:10.3762/bjoc.7.115

• significant challenge in gold catalysis. Results and Discussions Recently, our group reported the synthesis and characterization of the 1,2,3-triazole [36][37][38][39][40] coordinated gold(I) complexes. As revealed by the X-ray crystal structures (Scheme 3), both neutral and anionic triazoles can coordinate

• the synthesis of allenes through gold activated alkynes. X-ray crystal structures of the two different types of 1,2,3-triazole–Au complexes. Synthesis of α-iodoenone compounds from propargyl esters. The reaction substrate scope.a Different migrating groups.a Supporting Information Supporting

Advances in synthetic approach to and antifungal activity of triazoles

• Kumari Shalini,
• Nitin Kumar,
• Sushma Drabu and
• Pramod Kumar Sharma

Beilstein J. Org. Chem. 2011, 7, 668–677, doi:10.3762/bjoc.7.79

• membered ring containing two carbon and three nitrogen atoms. Triazoles have two isomeric forms, i.e., 1,2,3-triazole (1) and 1,2,4-triazole (2) (Figure 1). Triazoles are basic aromatic heterocyclic compounds. 1,2,3-Triazoles are surprisingly stable compared to other organic compounds with three adjacent

• occupies the most important place in the treatment of fungal diseases. The triazole derivatives noted below were synthesized by various groups and show antifungal activity. Novel 1,2,3-triazole-linked with β-lactam–bile acid conjugates were prepared via 1,3-dipolar cycloaddition reactions of azido β

• lipolytica and Fusarium oxysporum. (4R)-N-((1-((2S,3R)-2-(4-chlorophenyl)-1-(4-methoxyphenyl)-4-oxoazetidin-3-yl)-1H-1,2,3-triazole-4-yl)methyl)-4-((3R,5R,10R,12S,13R)-hexadecahydro-3,12-dihydroxy-5,10,13-trimethyl-1H-cyclopenta[a]phenanthren-17-yl)pentanamide (3, Figure 2) had the most potent activity [20

An overview of the key routes to the best selling 5-membered ring heterocyclic pharmaceuticals

• Marcus Baumann,
• Ian R. Baxendale,
• Steven V. Ley and
• Nikzad Nikbin

Beilstein J. Org. Chem. 2011, 7, 442–495, doi:10.3762/bjoc.7.57

• carbamate which was then converted into triazolone 314 by a double condensation reaction with hydrazine and formamidine. Finally, simple attachment of an isobutyl group completes the synthesis (Scheme 60). 1,2,3-Triazole Rufinamide (315, Inovelon) is Novartis’ new CNS-active compound used in the treatment

Dimerization of propargyl and homopropargyl 6-azido- 6-deoxy- glycosides upon 1,3-dipolar cycloaddition

• Nikolas Pietrzik,
• Daniel Schmollinger and
• Thomas Ziegler

Beilstein J. Org. Chem. 2008, 4, No. 30, doi:10.3762/bjoc.4.30

• series of 1,2,3-triazole containing per-O-acetyl-glycosides which were prepared by copper-catalyzed 1,3-dipolar cycloaddition either between fully acetylated propargyl 1-thio-glycosides and t-butyl (S)-4-azido-3-fluorenylmethyloxycarbamido-butyrate or between Fmoc-L-Asp(OtBu)-propargyl amide and 2,3,4,6

• -tetra-O-acetyl-glycosyl azides and ethyl 2,3,4-tri-O-acetyl-6-azido-6-deoxy-1-thio-glycosides, respectively [12]. In order to increase the structural diversity of glycosyl amino acid building blocks containing 1,2,3-triazole spacers even more, we next looked at the possibility to use glycosides bearing

• rings containing two sugar moieties and two 1,2,3-triazole moieties. For instance, such compounds may function as novel ligands for the preparation of metal complexes [24]. Further examples for cyclizations of other azido-alkynyl-glycosides are under investigation. Schematic representation of

Synthesis of new triazole- based trifluoromethyl scaffolds

• Michela Martinelli,
• Thierry Milcent,
• Sandrine Ongeri and
• Benoit Crousse

Beilstein J. Org. Chem. 2008, 4, No. 19, doi:10.3762/bjoc.4.19

• scaffolds. Keywords: copper; catalysis; fluorine; heterocycle; click chemistry; peptidomimetics; Background The 1,2,3-triazole system has widespread uses, and it has been considered as an interesting component in terms of biological activity [1][2][3][4][5]. Although the use of heterocyclic moieties in

An easy synthesis of 5-functionally substituted ethyl 4-amino- 1-aryl- pyrazolo- 3-carboxylates: interesting precursors to sildenafil analogues

• Said A. S. Ghozlan,
• Khadija O. Badahdah and
• Ismail A. Abdelhamid

Beilstein J. Org. Chem. 2007, 3, No. 15, doi:10.1186/1860-5397-3-15

• into 1,2,3-triazole 12 utilizing the reaction conditions described earlier in literature [11] failed. However, the amidooxime 11 cyclizes smoothly via loss of ethanol in DMF and in presence of anhydrous sodium acetate into isoxazolone 13. (cf. Scheme 4) Conclusion We could show that

2-Arylhydrazononitriles as building blocks in heterocyclic synthesis: A novel route to 2-substituted- 1,2,3-triazoles and 1,2,3-triazolo[4,5-b]pyridines

• Saleh M. Al-Mousawi and
• Moustafa Sh. Moustafa

Beilstein J. Org. Chem. 2007, 3, No. 12, doi:10.1186/1860-5397-3-12

• . Instead the hydrolyzed product 5 was formed. Introduction Interest in 1,2,3-triazole chemistry has recently been revived. [1][2][3][4] Zaprinast (1) is used as cyclic AMP phosphodiasterase inhibitor. [5] Plenty of 1,2,3-triazoles have also been reported to have useful pharmaceutical potential. [6][7][8

• ][9] Synthetic approaches to 1,2,3-triazoloazines are rather limited. There are in fact few known routes to 4-functionally substituted 1,2,3-triazole-5-amines. [7] The latter is one of the logical starting points for condensed 1,2,3-triazoloazines. In the present article we provide a versatile route

• . Formation of amidooximes on reacting 2-arylhydrazononitriles with hydroxylamine hydrochloride under similar conditions has been reported earlier by Elnagdi et al. [10][11] Attempted cyclization of 3 into 1,2,3-triazole via reflux in acetic anhydride, as has been reported recently, [11] afforded a product