76114-73-3Relevant articles and documents
One-pot, three-step preparation of alkyl and aryl alkylcarbamates from S-methyl N-alkylthiocarbamates
Artuso, Emma,Degani, Iacopo,Fochi, Rita,Magistris, Claudio
experimental part, p. 1612 - 1618 (2009/04/03)
A general procedure for the synthesis of alkyl and aryl alkylcarbamates starting from the corresponding 5-methyl N-alkylthiocarbamates is described. This procedure consists of three steps that are carried out in a one-pot fashion, without isolating the intermediate N-alkylcarbamoyl chlorides or alkyl isocyanates. All the target products were obtained in high yields (16 examples, average yield 91%). To be noted is the recovery of a co-product of industrial interest, dimethyl disulfide, in a half mole amount for each mole of thiocarbamate, with complete exploitation of the reagent. The alkyl isocyanates, if required, can also be isolated in high yields. Georg Thieme Verlag Stuttgart.
Base catalyzed cyclization of N-aryl and N-alkyl-O-propargyl carbamates to 4-alkylidene-2-oxazolidinones
Ramesh, Ramapanicker,Chandrasekaran, Yogesh,Megha, Rajendran,Chandrasekaran, Srinivasan
, p. 9153 - 9162 (2008/02/10)
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.
New polymer-supported allyloxycarbonyl (Alloc) and propargyloxycarbonyl (Proc) amino-protecting reagents
Chinchilla, Rafael,Dodsworth, David J.,Nájera, Carmen,Soriano, José M.
, p. 809 - 812 (2007/10/03)
New polymer-supported reagents, Alloc-P-OSu and Proc-P-OSu, have been prepared from a polymeric N-hydroxysuccinimide (P-HOSu), and used as solid-supported reagents for the allyloxycarbonyl (Alloc) and propargyloxycarbonyl (Proc) protection of the amino group. These new polymeric reagents are safe and stable, the residual P-HOSu generated after the protection reaction can be easily separated by simple filtration and reused.