Microwave-assisted synthesis of 1-aryl-5-(trifluoromethyl)-1H-tetrazoles

Synthesis of new (trifluoromethyl)-1H-benzo[e][1,2,4]triazolo[1,2-a][1,2,4]triazine-1,3(2H)-diones and (trifluoromethyl)benzo[5,6][1,2,4]triazino [1,2-b]phthalazine-8,13-diones

“…The electron-withdrawing properties of CF3 group enhanced the electrophilicity in functional of molecule 16a-d and therefore makes some partially fluorinated compounds valuable precursor for synthesis of new heterocyclic containing fluorine atom. [17][18][19][20] Due to the important of urazole and phthalazide derivatives and organofluorine compounds especially trifluoromethylated heterocyclics, in chemistry, drug and medicinal chemistry and in continuation of our research on the synthesis of trifluoromethylated compounds from imidoyl halides [21][22][23][24][25] , the present work aimed at the synthesis of fused trifluoromethylated heteropolycyclic nitrogen systems containing a fused urazole or phthalazide moiety starting from imidoyle chlorides.…”

Metal‐Free Synthesis of 5‐Trifluoromethyl‐1,2,4‐Triazoles from Iodine‐Mediated Annulation of Trifluoroacetimidoyl Chlorides and Hydrazones

“…[2] In general, there are two mainstream pathways to access to versatile trifluoromethyl-substituted N-heterocycles: 1 st ) trifluoromethylation of pre-synthesized N-heterocycles by the employment of diverse trifluoromethyl reagents; [3] 2 ed ) direct construction of trifluoromethyl-substituted N-heterocycles through the reaction of different trifluoromethyl-containing synthons with suitable coupling substrates. [6][7][8][9][10][11][12] Trifluoroacetimidoyl halides were usually applied as useful building blocks for the assembly of trifluoromethyl-substituted N-heterocycles in synthetic organofluorine chemistry. [6][7][8][9][10][11][12] Trifluoroacetimidoyl halides were usually applied as useful building blocks for the assembly of trifluoromethyl-substituted N-heterocycles in synthetic organofluorine chemistry.…”

“…In 2010, the research groups of Wu [6a] and Zhang [6b] reported palladium-or coppercatalyzed cyclization of trifluoroacetimidoyl chlorides with sodium hydrosulfide hydrate to synthesize 2trifluoromethylbenzothiazoles, respectively (Scheme 1a). [8] The Wu's group developed an novel Au-catalyzed protocol for the synthesis of 2-fluoroalkyl imidazole derivatives from trifluoroacetimidoyl chloride and propargyl amines (Scheme 1d). [7] Two years later, Darehkordi's group explored a convenient approach for the preparation of 5-trifluoromethyl-tetrazoles via microwave-assisted [2 + 3] cycloaddition reaction of trifluoroacetimidoyl chloride and sodium azide.…”

“…[4] In this context, in contrast to the frequent application of 2,2,2trifluorodiazoethane (CF 3 CHN 2 ) as an appealing trifluoromethyl-containing 1,3-dipole to build numer-ous trifluoromethyl-substituted N-heterocycles, [5] the using of trifluoroacetimidoyl halide as trifluoromethyl synthon is proven to be exceptional in many cases. [6][7][8][9][10][11][12] Trifluoroacetimidoyl halides were usually applied as useful building blocks for the assembly of trifluoromethyl-substituted N-heterocycles in synthetic organofluorine chemistry. In 2010, the research groups of Wu [6a] and Zhang [6b] reported palladium-or coppercatalyzed cyclization of trifluoroacetimidoyl chlorides with sodium hydrosulfide hydrate to synthesize 2trifluoromethylbenzothiazoles, respectively (Scheme 1a).…”

An Improved One-pot Method for the Synthesis of 1,5-Disubstituted Tetrazoles from Secondary amides using Titanium Tetrachloride (TiCl4)

“…The synthesis of 1,5-disubstituted tetrazole is well described in literature, where it can be synthesized from amides, 11 thioamides, 12 imidoyl chlorides, 13 imidoyl benzotriazoles, 14 oximes, 15 isocyanates, 16 etc. Out of these, the secondary amides are easily available or can be easily prepared from amines, so the interest has been created towards the use of amides in the synthesis of 1,5-disubstituted tetrazoles.…”