Synthesis of 2H-1,2,3-Triazoles

Facile Quenching and Spatial Patterning of Cylooctynes via Strain-Promoted Alkyne–Azide Cycloaddition of Inorganic Azides

“…In a scaled-up reaction, we managed to isolate 53% of the triazole 8 and 20% of the methyl vinyl ether 9 , the latter the apparent product of methanol addition across the triple bond (Scheme 4). 15 The second byproduct decomposes on the silica gel column during separation, but by analogy with the formation of 9 , we suggest that it is produced by the hydration of 1 in the course of the reaction.…”

“…HPLC analysis of the reaction mixtures starting with 2 or 4 showed complete consumption of the cyclooctyne and the formation of a single product in the reactions 15 . HRMS analysis 15 confirmed that a single triazole product was formed in each of these two reactions ( 5 and 6 of Scheme 3, respectively). However, two products were observed chromatographically when a p-iodobenzoate derivative of DIBO (DIBO-IBA, 3a ) was reacted with sodium azide.…”

“…It is interesting to note, that triazole 8 and cyclooctyne 1 are stable in PBS with 5% methanol, their UV spectra 15 showing no signs of decomposition after overnight incubation and no detectable amounts of 9 were seen by HPLC. This observation suggests that azide ion somehow catalyzes the methanol addition across the triple bond…”

“…8 The specificity and convenience of the cycloaddition reaction with an essentially limitless variety of organic azides has led to a steadily growing range of applications of SPAAC reagents in chemical synthesis and biology, usually as a selective conjugation tool. The popular SPAAC reagents ODIBO 9 , ADIBO 10,11 (a.k.a DIBAC 12 or DBCO), DIBO 13 , and BCN 14 are known to differ dramatically in their respective reaction rates with organic azides 9,10,13,15 , but little is known about their reactivity with inorganic azides. Our interest in SPAAC reactivity with inorganic azides was provoked by the intermittent failure of a cyclooctyne labeling experiment.…”

Crystal structure of 2-((3-(5-methyl-1-phenyl-1H-1,2,3-triazol-4-yl)-1-phenyl-1H-pyrazol-4-yl)methylene)-1H-indene-1,3(2H)-dione, C28H19N5O2

“…1,2,3-Triazoles [2][3][4][5][6] are known for their biological applications such as antidiabetic, anti-in ammatory, antifungal, antiviral and antibacterial activity [7][8][9]. In the title crystal structure, the asymmetric unit consists of one molecule of C 28 H 19 N5O 2 .…”