Azobenzene dye-coupled quadruply hydrogen-bonding modules as colorimetric indicators for supramolecular interactions

• Yagang Zhang and
• Steven C. Zimmerman

Beilstein J. Org. Chem. 2012, 8, 486–495, doi:10.3762/bjoc.8.55

• produced crude 16, which was used directly in the next step without purification. Coupling of azide 16 with the known 17 [34] was successfully effected under standard conditions for the copper-catalyzed azide–alkyne cycloaddition [55]. Azobenzene dye-coupled DeUG module 18 was obtained as an orange–yellow

• -diamido-1,8-naphthyridine (DAN) unit was linked to azobenzene dyes through one of its amide groups, giving compounds 5, 8, and 10, and the 7-deazaguanine urea (DeUG) unit was linked to an azobenzene dye by a Steglich esterification, giving 12, or by the copper-catalyzed azide–alkyne cycloaddition (click

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

• )methyl]aziridines by Cu(I)-catalyzed azide-alkyne cycloaddition, followed by microwave-assisted, regioselective ring opening by dialkylamine towards 1-(2,3-diaminopropyl)-1,2,3-triazoles. Although most of these compounds exhibited weak antiplasmodial activity, six representatives showed moderate

• -triazol-1-yl)methyl]aziridines by Cu(I)-catalyzed azide-alkyne cycloaddition, followed by microwave-assisted, regioselective ring opening by diethyl- or dimethylamine towards the corresponding 1-(2,3-diaminopropyl)-1,2,3-triazoles. From a synthetic viewpoint, new insights were provided concerning the

• water-induced ring opening of nonactivated cis- and trans-2-aryl-3-(hydroxymethyl)aziridines and with respect to the synthesis and use of 1-arylmethyl-2-(azidomethyl)aziridines for azide-alkyne cycloaddition reactions. From a biological viewpoint, most of these compounds exhibited weak antiplasmodial

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

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

• ). Itraconazole (10). Voriconazole (11). Posaconazole (12). Ravuconazole (13). Copper catalyzed azide–alkyne cycloaddition. Ruthenium catalyzed azide–alkyne cycloaddition. Copper-sulfate catalyzed azide–alkyne cycloaddition. Azide–dimethylbut-2-yne-dioate cycloaddition.

Synthesis of glycoconjugate fragments of mycobacterial phosphatidylinositol mannosides and lipomannan

• Benjamin Cao,
• Jonathan M. White and
• Spencer J. Williams

Beilstein J. Org. Chem. 2011, 7, 369–377, doi:10.3762/bjoc.7.47

• –alkyne cycloaddition (CuAAC) reaction [33][34]. Results and Discussion Since their introduction by Palcic and co-workers [35], hydrophobic alkyl glycosides have proven to be valuable derivatives for enzymatic assays, as their lipophilic nature allows easy product isolation by either reversed-phase

• ) lipophilicity allowing biphasic partitioning between butanol/water or purification by reversed-phase extraction, (ii) ability to be reduced to an aminooctyl chain for use in squarate conjugation chemistry, and (iii) capacity to be conjugated with fluorescent terminal alkynes using the Cu(I)-catalyzed azide