Synthesis and cell imaging applications of fluorescent mono/di/tri-heterocyclyl-2,6-dicyanoanilines

Tandem synthesis of 1-formyl-1,2,3-triazoles

“…26,27 With the aldehyde group an attractive handle for synthetic diversification, such compounds have also served as synthons for preparing bioimaging, 28 anti-cancer, 23,24 and antituberculosis 26,27 agents. Likewise, 4-imino-1,2,3-triazoles formed from amine condensation reactions have been shown to be useful for constructing novel coordination compounds.…”

1-(4-Nitrophenyl)-1H-1,2,3-Triazole-4-carbaldehyde: Scalable Synthesis and Its Use in the Preparation of 1-Alkyl-4-Formyl-1,2,3-triazoles

“…4-Formyl-1,2,3-triazoles, also known as 1,2,3-triazole-4-carbaldehydes, are widely present in the literature, mainly due to the synthetic versatility of the formyl group [1][2][3][4][5][6][7]. In the field of medicinal chemistry [7], triazole-4-carbaldehydes have been prepared as intermediates in the synthesis of anticancer [8][9][10], antifungal [11,12], antituberculosis [13][14][15], anti-inflammatory [10,16], antidiabetic [17], and even bioimaging agents [18]. Furthermore, imine derivatives have been synthesized as interesting ligands in coordination chemistry [19][20][21].…”

“…Furthermore, imine derivatives have been synthesized as interesting ligands in coordination chemistry [19][20][21]. 1-Substituted 4-formyl-1,2,3-triazoles are commonly prepared via a two-step synthesis involving the copper-catalyzed azide-alkyne cycloaddition reaction with azides and propargyl alcohol [2,[9][10][11][12][13][15][16][17][18]22] or acetal-protected propargyl aldehydes [3,5,6,8,23,24], followed by oxidation or hydrolysis, respectively. These methods are clever alternatives for the cycloaddition between azides and the low boiling propynal, which is inconvenient to handle.…”

“…These methods are clever alternatives for the cycloaddition between azides and the low boiling propynal, which is inconvenient to handle. Commonly used oxidants include manganese dioxide [11,12,18], 2-iodoxybenzoic acid (IBX) [13,15,17], and hexavalent chromium compounds [2,9,10,16,22]. Despite their wide application, a few drawbacks of the coppercatalyzed click reactions can be named.…”

Synthesis of 3,5‐Diaryl‐2,6‐dicyanoanilines from Tandem Reactions of Ynones with Malononitrile

“…2,6‐Dicyanoanilines are useful intermediates for organic synthesis . They also have been used as optical materials and cell image agents . The reported synthetic methods for 2,6‐dicyanoanilines include i) three‐component reactions of aldehydes, ketones and malononitrile; ii) reactions of chalcones with malononitrile in guanidinium ionic liquids; iii) three‐component reactions of α,β‐unsaturated imines with malononitrile; iv) reactions of aldehydes, β‐nitroolefins and malononitrile catalyzed by DMAP; v) reactions of 1,3‐diketones with three equiv.…”