Morpholine-mediated defluorinative cycloaddition of gem-difluoroalkenes and organic azides

• Tzu-Yu Huang,
• Mario Djugovski,
• Sweta Adhikari,
• Destinee L. Manning and
• Sudeshna Roy

Beilstein J. Org. Chem. 2023, 19, 1545–1554, doi:10.3762/bjoc.19.111

• plausible pathways. Attractive elements include the regioselective and straightforward direct synthesis of fully substituted 1,2,3-triazoles, which are otherwise difficult to access, from readily available starting materials. Keywords: [3 + 2] cycloaddition; defluorination; fully decorated 1,2,3-triazoles

• ] cycloaddition reaction utilizing gem-difluoroalkenes, which inherently exhibit attenuated activity compared to the activated α-CF3 carbonyls. This report provides a highly regioselective and novel way to access C-4-morpholine-functionalized fully decorated 1,2,3-triazoles from gem-difluoroalkenes and organic

• -fluorophenyl)-5-(p-tolyl)-1H-1,2,3-triazol-4-yl)morpholine (4e), one of the fully decorated 1,2,3-triazoles (Figure 4). The peak at 7.59 ppm (d, J = 8.1 Hz) in the 1H NMR spectrum corresponding to the H1 protons of the C-5-aryl substituent on the 1,2,3-triazole ring shows a cross-peak with the protons of the C

A recent overview on the synthesis of 1,4,5-trisubstituted 1,2,3-triazoles

• Pezhman Shiri,
• Ali Mohammad Amani and
• Thomas Mayer-Gall

Beilstein J. Org. Chem. 2021, 17, 1600–1628, doi:10.3762/bjoc.17.114

• ]. In recent years, fully substituted 1,2,3-triazole derivatives have been studied by many research groups (Scheme 1). Among an extensive range of 1,2,3-triazoles, fully decorated 1,2,3-triazoles display a sort of outstanding substance found in plenty biologically important molecules and functionalized

• achieved by a tautomerization process. A highly decorated 1,2,3-triazole 11 was formed via cyclization of the intermediate 17 along with the loss of one molecule of TsNH2 [41]. Fully decorated 1,2,3-triazoles 19 containing a sulfur-based side chain have been synthesized via a cyclization of β-thiolated

• EDAMs (R1 ≠ R2) were also applied to check the regioselectiveness of this addition and cyclization reaction. The methodology provides a simple, straightforward, and facile path to access fully decorated 1,2,3-triazoles 25 in moderate to good yield. Noticeably, this uncatalyzed addition and cyclization