183284-64-2

Upstream product

• 106-49-0 p-toluidine 
• 2327-67-5 N-(p-tolyl)-P,P,P-triphenylphosphine imide 
• 134-81-6 benzil 
• 2101-86-2 p-methylazidobenzene 

Downstream Products

• 5722-91-8 1,2-diphenyl-2-(phenylamino)ethanone 
• 10205-58-0 6-methyl-2-phenyl-1,3-benzothiazole 
• 78604-82-7 α-p-toluidino-deoxybenzoin 
• 856410-28-1 α'-p-toluidino-bibenzyl-α-ol 
• 351217-77-1 7-methyl-2,3-diphenyl-2H-benzo[1,4]thiazine 

Relevant academic research and scientific papers

Br?nsted Base-Catalyzed Formal Reductive [3+2] Annulation of 4,4,4-Trifluorocrotonate and α-Iminoketones

A formal reductive [3+2] annulation of 4,4,4-trifluorocrotonate and α-iminoketones was developed under Br?nsted base catalysis. A single phosphazene base efficiently catalyzes the one-pot tandem reaction involving two mechanistically different elementary processes, namely the chemoselective reduction of an imine moiety of α-iminoketones with thiols as the reductant and the subsequent intermolecular Michael addition of an enolate of α-aminoketones concomitant with lactam formation. This operationally simple method provides β-trifluoromethyl-substituted γ-lactams with a tetrasubstituted carbon as a single diastereomer.

From benzil arylimines to 2H-benzo-1,4-thiazines, benzothiazoles or indoles

A series of benzil monoarylimines (1) was treated with phosphorus pentasulfide in refluxing toluene or xylene. Thionation of 1 occurred readily to afford either 2H-benzo-1,4-thiazines (2) or indoles (4) via annulation reactions, depending strongly on the nature of the meta substituent of the arylamino group. Mechanisms for these rearrangements were proposed. Furthermore, subsequent oxidation of 2 provided benzothiazoles (3). All compounds were fully characterized by IR, MS, 13C and 1H NMR.

Titanium(IV) chloride induced reactions of ketones and C-acylimines with dimethylcyanamide

The reactions of ketones (benzophenone, 4-methylbenzophenone, acetophenone, acetone, and 2,2,4,4-tetramethyl-3-pentanone) and C-acylimines with dimethylcyanamide in the presence of titanium(IV) chloride were investigated. Benzophenone and 4-methylbenzophenone react with dimethylcyanamide to give 4,4-disubstituted 2-dimethylamino-3-aza-1-oxa-1,3-butadienes 5 and 4,4-disubstituted 2-dimethylanuno-1-N,N-dimethylcarbamoyl-1,3-diaza-1,3-butadienes 9. Ketones with enolizable hydrogen atoms undergo aldol reactions under these conditions. C-Acylimines 11b-11e, derived from benzil and substituted anilines, undergo [2 + 2] cycloaddition to dimethylcyanamide with subsequent ring opening to 1-(N,N-dimethylcarbamoyl)-2,3,4-triaryl-1,4-diaza-1,3-butadienes 15. 1,2-Diphenyl-2-(isopropylimino)ethanone (11a) reacts with dimethylcyanamide to give 2-dimethylamino-1-isopropyl-4,4-diphenyl-2-imidazolin-5-one (23) in a hitherto unknown multistep reaction. The structure of 23 was confirmed by an X-ray analysis. VCH Verlagsgesellschaft mbH, 1996.