106932-28-9Relevant academic research and scientific papers
Titanium(IV) chloride induced reactions of ketones and C-acylimines with dimethylcyanamide
Mazik, Monika,Boese, Roland,Sustmann, Reiner
, p. 1665 - 1671 (1996)
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.
Zinc(ii)-mediated generation of 5-amino substituted 2,3-dihydro-1,2,4-oxadiazoles and their further ZnII-catalyzed and O2-involving transformations
Smirnov, Andrey S.,Yandanova, Ekaterina S.,Bokach, Nadezhda A.,Starova, Galina L.,Gurzhiy, Vladislav V.,Avdontceva, Margarita S.,Zolotarev, Andrey A.,Kukushkin, Vadim Yu.
, p. 9330 - 9344 (2015/12/01)
ZnII-activated cyanamides NCNR2 (R2 = Me2, Et2, C5H10, (CH2)2O(CH2)2, Ph2) react with the acyclic N-alkyl ketonitrones Phs
PYRIDINES. XIV - ACYLATION DE PYRIDYL-LITHIOENAMIDINES. SYNTHESE DE PYRIDYL-N-ACYLENAMIDINES ET DE PYRIDYLPYRIMIDONES-4.
Compagnon, Paul-Louis,Gasquez, Francoise,Kimny, Tan
, p. 57 - 64 (2007/10/02)
The mixture of PhLi:di- or tri-methylpyridine 1:PhCN:RCOCl (R = Me, Ph, EtO, Me2N) or PHCO2Me (molar ratio 3:1:3:3) leads through the intermediates primary lithioenamines 3 and lithioenamidines 4, to acylated products, N-acylenamines (enamides) 5, β-diketones and β-ketoesters 6, C-acylenamides 7, N-acyleneamidines 8 and their cyclization derivatives, pyridylhydroxypyrimidines 10 (yield up to 60 percent) and pyridyldihydropyrimidones 11 (yield up to 10 percent).Distillation of the crude extract leads to naphthyridones 12 (yield up to 10 percent) which result from thermocyclization of the enamides 5f, 5g and 7f.Various by-products are isolated such as N,N-dimethyl-N',N'-diphenylmethyleneurea resulting from N-lithiodiphenylketimine and phenacylpyridines 13.Crotonization and oxidation of the latter compounds lead to the aza-analogues 14, 15 of dibenzoylstilbenes.
