3004-45-3

Upstream product

• 35718-08-2 propargyl chloroformate 
• 108-42-9 3-chloro-aniline 
• 107-19-7 propargyl alcohol 
• 2909-38-8 m-chlorophenyl isocyanate 

Downstream Products

• 123567-34-0 4-<(2-bromoethyl)methylamino>-2-butynyl N-(3-chlorophenyl)carbamate 
• 123567-32-8 4-<(2-chloroethyl)methylamino>-2-butynyl N-(3-chlorophenyl)carbamate 
• 4836-81-1 4-bromo-2-butynyl N-(3-chlorophenyl)carbamate 
• 16418-07-8 4-(diethylamino)-2-butynyl N-(3-chlorophenyl)carbamate 
• 123567-38-4 4-<(2-hydroxyethyl)methylamino>-2-butynyl N-(3-chlorophenyl)carbamate 
• 39268-94-5 Chloromethyl-(3-chloro-phenyl)-carbamic acid prop-2-ynyl ester 

Relevant academic research and scientific papers

Base catalyzed cyclization of N-aryl and N-alkyl-O-propargyl carbamates to 4-alkylidene-2-oxazolidinones

The base catalyzed cyclization of N-aryl and N-alkyl-O-propargyl carbamates is studied in detail. The effect of various bases and solvents on the efficacy of this cyclization reaction is analyzed and a new base-solvent system (LiOH in DMF) for effective cyclization of these carbamates is reported. A number of differentially substituted O-propargyl carbamates were cyclized to the corresponding 2-oxazolidinones under these conditions. The reaction conditions reported here are mild and no side reactions were observed in any of the substrates studied. A propargyl carbonate group was unaffected during the course of the cyclization of the O-propargyl carbamate group. The propargyl carbamates were prepared from the corresponding alkyl or aryl amines and the corresponding propargyl chloroformate, resulting in oxazolidinones diversely substituted at the nitrogen atom. N-Aryl-O-propargyl carbamates cyclized readily to the corresponding oxazolidinones with LiOH in DMF, whereas N-alkyl-O-propargyl carbamates reacted slowly under the same conditions. O-Propargyl carbamates substituted at the 1-position tend to cyclize faster whereas those substituted at 3-position cyclize considerably slower than the unsubstituted carbamates.

Dimethylsulfonium analogues of the muscarinic agent McN-A-343: [4-[[N-3 or 4-halophenyl)carbamoyl]oxy]-2-butynyl]dimethylsulfonium perchlorates

Some 3- and 4-bromophenyl and dimethylsulfonium analogues of the muscarinic agent [4-[[N-(3-chlorophenyl)-carbamoyl]oxy]-2-butynyl]trimethylammonium chloride (McN-Al-343) (1) were synthesized. The new compounds were assayed for effects on arterial blood p

Mecanisme de la reaction de cyclisation en milieu aqueux de carbanilates de propargyle en methylene-4 oxazolidinones-2

Les cinetiques d'hydrolyse en milieu alcalin a 25 deg de chloro-3 carbanilates de propargyle ont ete suivies par spectrophotometrie ultraviolette.La catalyse complexe des ions hydroxyle, mis en evidence pour la reaction de cyclisation de ces composes en methylene-4 oxazolidinones-2 a ete interpretee comme resultant de l'attaque nucleophile de l'anion du substrat et de celle de l'ion hydroxyle sur la triple liaison.La premiere conduit directement a l'heterocycle alors que la seconde engendre un cetocarbamate qui se cyclise ulterieurement en oxazolidinone.