46167-77-5

Upstream product

• 106-96-7 propargyl bromide 
• 88-05-1 2,4,6-trimethylaniline 
• 108-67-8 1,3,5-trimethyl-benzene 

Downstream Products

• 1242029-37-3 C₁₇H₂₁NO 
• 1242029-53-3 C₁₈H₂₃NO 
• 1242029-54-4 C₂₂H₂₃NO 
• 1242029-33-9 C₁₆H₁₉NO 

Relevant academic research and scientific papers

Synthesis and biological evaluation of coumarin-linked 4-anilinomethyl-1,2,3-triazoles as potent inhibitors of carbonic anhydrases ix and xiii involved in tumorigenesis

A series of coumarin-linked 4-anilinomethyl-1,2,3-triazoles (6a–t) was synthesized via a molecular hybridization approach, through carbon C-6 of the coumarin moiety. The synthesized compounds were evaluated for their inhibition of carbonic anhydrase (CA)

A Metal-Free Direct Arene C?H Amination

The synthesis of aryl amines via the formation of a C?N bond is an essential tool for the preparation of functional materials, active pharmaceutical ingredients and bioactive products. Usually, this chemical connection is only possible by transition metal-catalyzed reactions, photochemistry or electrochemistry. Here, we report a metal-free arene C?H amination using hydroxylamine derivatives under benign conditions. A charge transfer interaction between the aminating reagents TsONHR and the arene substrates enables the chemoselective amination of the arene, even in the presence of various functional groups. Oxygen was crucial for an effective conversion and its accelerating role for the electron transfer step was proven experimentally. In addition, this was rationalized by a theoretical study which indicated the involvement of a dioxygen-bridged complex with a “Sandwich-like” arrangement of the aromatic starting materials and the aminating agents at the dioxygen molecule. (Figure presented.).

140. Acid-Catalyzed -Sigmatropic Rearrangements of N-Propargylanilines

The acid-catalyzed rearrangement of N-(1',1'-dimethylprop-2'-ynyl)-, N-(1'-methylprop-2'-ynyl)-, and N-(1'-arylprop-2'-ynyl)-2,6-, 2,4,6-, and 2,3,5,6-, and 2,3,4,5,6-substituted anilines in mixtures of 1N aqueous H2SO4 and ROH such as EtOH, PrOH, BuOH etc., or in CDCl3 or CCl4 in the presence of 4 to 9 mol-equiv. trifluoroacetic acid (TFA) has been investigated (cf.Scheme 12-25 and Tables 6 and 7).The rearrangement of N-(3'-X-1',1'-dimethyl-prop-2'-ynyl)-2,6- and 2,4,6-trimethylanilines (X = Cl, Br, I) in CDCl3/TFA occurs already at 20 deg C with τ1/2 of ca. 1 to 5 h to yield the corresponding 6-(1'-X-3'-methylbuta-1',2'-dienyl)-2,6-dimethyl- or 2,4,6-trimethylcyclohexa-2,4-dien-1-iminium ions (cf.Scheme 13 and Footnotes 26 and 34).When the 4 position is not substituted, a consecutive -sigmatropic rearrangement takes place to yield 2,6-dimethyl-4-(3'-X-1'1'-dimethylprop-2'-ynyl)anilines (cf.Footnotes 26 and 34).A comparable behavior is exhibited by N-(3'chloro-1'-phenylprop-2'-ynyl)-2,6-dimethylaniline (45; cf.Table 7).The acid-catalyzed rearrangement of the anilines with a Cl substituent at C(3') in 1N aqueous H2SO4/ROH at 85-95 deg C, in addition, leads to the formation of 7-chlorotricyclo2,7>oct-3-en-8-ones as the result of an intramolecular Diels-Alder reaction of the primarily formed iminium ions followed by hydrolysis of the iminium function (or vice versa; cf.Schemes 13, 23, and 25 as well as Table 7).When there is no X substituent at C(1') of the iminium-ion intermediate, a -sigmatropic shift of the allenyl moity at C(6) occurs in competition to the -sigmatropic rearrangement to yield the corresponding 3-allenyl-substituted anilines (cf.Schemes 12, 14-18, and 20 as well as Tables 6 and 7).The rearrangement of (-)-(S)-N-(1'phenylprop-2'-ynyl)-2,6-dimethylaniline ((-)-38; cf.Table 7) in a mixture of 1N H2SO4/PrOH at 86 deg C leads to the formation of (-)-(R)-3-(3'-phenylpropa-1',2'-dienyl)-2,6-dimethylaniline ((-)-91), (+)-(E)- and (-)-(Z)-6-benzylidene-1,5-dimethyltricyclo2,7>oct-3-en-8-one ((+)-(E)- and (-)-(Z)-92, respectively), and (-)-(S)-2,6-dimethyl-4-(1'-phenylprop-2'-ynyl)aniline ((-)-93).Recovered starting material (10percent) showed a loss of 18percent of its original optical purity.On the other hand, (+)-(E)- and (-)-(Z)-92 showed the same optical purity as (-)-38, as expected for intramolecular concerted processes.The CD of (+)-(E)- and (-)-(Z)-92 clearly showed that their tricyclic skeletons possess enantiomorphic structures (cf.Fig. 1).Similar results were obtained from the acid-catalyzed rearrangement of (-)-(S)-N-(3'-chloro-1'-phenylprop-2'-ynyl)-2,6-dimethylaniline ((-)-45; cf.Table 7).The recovered starting material exhibited in this case a loss of 48percent of its original optical purity, showing that the Cl substituent favors the heterolytic cleavage of the N-C(1') bond in (-)-45.A still higher degree (78percent) of loss of optical activity of the starting aniline ...