1933-73-9Relevant academic research and scientific papers
A one-pot stereoselective synthesis of electron-deficient 4-substituted (E, E)-1-arylsulfonylbuta-1,3-dienes and their chemoselective [3+2] cycloaddition with azomethine ylides - A simple synthesis of 1,3,4-trisubstituted pyrrolidines and pyrroles
Sankar, Ulaganathan,Mahalakshmi, Susarla,Balasubramanian, Kalapattukuppuswamy
supporting information, p. 1533 - 1540 (2013/08/23)
A simple and efficient method for the synthesis of (E,E)-1-(arylsulfonyl) buta-1,3-dienes bearing electron-withdrawing substituents like cyano and ethoxycarbonyl at position 4, involving a one-pot alkylation of bis(phenylsulfonyl)methane with trans-ethyl 4-bromocrotonate/trans-4- bromocrotononitrile, and elimination of arylsulfinic acid, is described. These dienes undergo facile mono [3+2] cycloaddition with azomethine ylides chemoselectivity to furnish functionalized 1,3,4-trisubstituted pyrrolidines. Oxidation of these cycloadduct with MnO2·SiO2 under mild conditions provides 1,3,4-trisubstituted pyrroles. Georg Thieme Verlag Stuttgart. New York.
