183284-64-2Relevant articles and documents
Br?nsted Base-Catalyzed Formal Reductive [3+2] Annulation of 4,4,4-Trifluorocrotonate and α-Iminoketones
Kondoh, Azusa,Terada, Masahiro
, p. 585 - 588 (2021)
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.
Titanium(IV) chloride induced reactions of ketones and C-acylimines with dimethylcyanamide
Mazik, Monika,Boese, Roland,Sustmann, Reiner
, p. 1665 - 1671 (2007/10/03)
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.