One-Pot, Three-Step Copper-Catalyzed Five-/Four-Component Reaction Constructs Polysubstituted Oxa(Thia)zolidin-2-imines

Abstract A novel one-pot synthesis of polysubstituted oxa(thia)zolidin-2-imines has been developed. It employs A 3 -coupling of aldehyde and amine with alkyne to form propargyl amine, which on (thio)amidation with iso(thio)cyanate produces N -propargyl(thio)urea, and a cyclization reaction. A 5- exo...

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Bibliographic Details
Published in:Synlett 2012-08, Vol.23 (13), p.1955-1959
Main Authors: Madaan, Chetna, Saraf, Shuddham, Priyadarshani, Garima, Reddy, P. Purushotham, Guchhait, Sankar K., Kunwar, A. C., Sridhar, B.
Format: Article
Language:English
Subjects:
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
letter
Organic chemistry
Preparations and properties
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Summary:Abstract A novel one-pot synthesis of polysubstituted oxa(thia)zolidin-2-imines has been developed. It employs A 3 -coupling of aldehyde and amine with alkyne to form propargyl amine, which on (thio)amidation with iso(thio)cyanate produces N -propargyl(thio)urea, and a cyclization reaction. A 5- exo -dig iodocyclization of N -propargylurea constructs 5-iodomethyleneoxazolidin-2-imine, while cycloisomerization of the thio analogue provides 5-methylenethiazolidin-2-imine. In this process, CuI catalysis has been found to be crucial, and the cyclization occurs through oxygen/sulfur (not nitrogen) nucleophilic attack to alkyne.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0032-1316606