19642-36-5Relevant academic research and scientific papers
TRIETHYLAMINE, ETHANOL- MEDIATED DISCIPLINED REACTIONS OF S-BENZYLISOTHIOURONIUM CHLORIDE WITH UNSATURATED 2-OXAZOLIN-5-ONES: SYNTHESIS OF (Z)-2-AMINO-4-ARYLMETHYLENE-2-IMIDAZOLIN-5-ONES, 5-BENZOYLAMINO-2-BENZYLTHIO-6-OXO-4,4-SPIROCYCLOHEXYL-1,4,5,6-TETRA
Mukerjee, Arya K.,Joseph, Kiran,Homami, Seyed-Saied,Tikdari, Ahmad M.
, p. 1317 - 1325 (2007/10/02)
Triethylamine-mediated condensation of S-benzylisothiouronium chloride with (Z)-4-arylmethylene-2-phenyl-2-oxazolin-5-ones (4) in ethanol gives (Z)-2-amino-4-arylmethylene-2-imidazolin-5-ones (7), whereas the similar reaction with 4-cyclohexylidene-2-phen
Studies on Conjugated Nitriles. IV. Reaction of Ethyl Cyanoformate with Organomagnesium, -zinc, and - cadmium Reagents, and Phosphonium Ylide
Akiyama, Yasunobu,Takebayashi, Shoko,Kawasaki, Tomomi,Sakamoto, Masanori
, p. 1800 - 1807 (2007/10/02)
The reaction of ethyl cyanoformate (1a) with phenylcadmium bromide (3a) gave ethyl benzoate (4), ethyl 2-phenyl-2-oxoacetate (5a), and 2-ethoxycarbonyl-2,4-diphenyl-3-imidazoline-5-one (6).In the presence of zinc chloride, the addition of 3a to the cyano group of 1a occured to give only 5a.The similar reaction of 1a with other organocadmium reagents (3b-f) in the presence of zinc chloride gave the corresponding α-ketoesters (5b-f) in moderate yields.The reactions of 1a with other organometallic reagents, e.g. phenylmagnesium (2a), -zinc (8) and -mercuric bromide (9) in the presence or in the absence of zinc chloride were examined.Furthermore, the addition of phosphonium ylide 13a to the cyano group of 1a in the presence of stannic chloride occured exclusively to give the phosphonium salt 14.The results are discussed in terms of the hard and soft acids and bases (HSAB) principle.Keywords - ethyl cyanoformate; benzoyl cyanide; organocadmium reagent; organozinc reagent; phosphonium ylide; cyano group addition; α-ketoester; α-dehydroamino ester; Lewis acid
REACTION OF ORGANOCADMIUM REAGENTS WITH ETHYL CYANOFORMATE: PREPARATION OF α-KETO ESTERS
Akiyama, Yasunobu,Kawasaki, Tomomi,Sakamoto, Masanori
, p. 1231 - 1232 (2007/10/02)
Organocadmium reagents reacted with the cyano-function of ethyl cyanoformate in the presence of ZnCl2 to afford the corresponding α-keto esters.
