Abstract:HELMUT SCHMIDHAMMER and ARNOLD BROSSI. Can. J. Chem. 60, 3055 (1982).Bischler-Napieralski cyclization of the known phenylacetamide 1, followed by selective ether cleavage of the 3,4-dihydroisoquinoline 2 and sodium borohydride reduction, afforded the tetrahydroisoquinoline 4. Optical resolution of 4 with tartaricacid gave the optical isomers 4a, b , which were converted into the 6-ketomorphinans 9 0 , b and their 0-methyl ethers 100, b by the following reaction sequence: Birch reduction, N-formylation of the d… Show more
“…19 The off-white precipitate of DFO formamide was isolated by vacuum evaporation and filtration followed by re-crystallization from n-propanol (90% yield). The DFO dissolved during refluxing and the resulting formylated DFO derivative precipitated after subsequent cooling.…”
“…19 The off-white precipitate of DFO formamide was isolated by vacuum evaporation and filtration followed by re-crystallization from n-propanol (90% yield). The DFO dissolved during refluxing and the resulting formylated DFO derivative precipitated after subsequent cooling.…”
“…Heating with phenyl or ethyl formate is comparatively a better method, but the procedure requires very high‐temperature and it is more time ‐ consuming . An attractive path for formamide synthesis is the N‐formylation reaction between CO 2 and amines with suitable reducing agent.…”
Chemical fixation of carbon dioxide through suitable catalytic pathways is very demanding in the context of sustainable environment. An environmentally benign synthetic studies of N‐formylated amine derivatives by carbon dioxide fixation of amines have been investigated in presence of Merrifield resin supported palladium nanomaterial (Pd‐PS‐amtp catalyst) at ambient temperature. Poly(methylhydrosiloxane) was employed as a susceptible hydride transferring agent in the present CO2 fixation reaction. Further this catalyst exhibited an extended catalytic activity for the production of organic carbamates from dimethyl carbonate and aromatic amines. The Pd‐PS‐amtp nanomaterial has been produced by two step strategies and systematically characterized by FTIR, UV‐Vis, FE‐SEM and TGA‐DTA analysis. The benefits of this system are quite economical, high recycling efficiency and consuming short reaction time to allow significant product yield. The production of organic carbamates in presence of the present catalyst is a phosgene‐free procedure where dimethyl carbonate (DMC) is utilized both as carboxylating agent and solvent. The recovery of Pd‐PS‐amtp nanomaterial could easily be performed after the reactions and recyclable up to six times without considerable reduction in catalytic activity.
A fast, efficient and simple route for the N-formylation of amines has been developed by treating amines with 85% formic acid at room temperature in the presence of 5 mol% of bromodimethylsulfonium bromide as catalyst under solvent-free condition. This method provides a green and much improved protocol over the existing methods.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.