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LiO t Bu Promoted 5‐ Exo– dig Cyclization of Propargyl Alcohols and Isocyanates for the Synthesis of Multisubstituted 3 H ‐Oxazol‐2‐ones and Oxazolidin‐2‐ones
Author(s) -
Savarimuthu S. Antony,
Thomas S. Augustine,
Prakash D. G. Leo,
Gandhi Thirumanavelan
Publication year - 2016
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201600363
Subject(s) - propargyl , chemistry , substituent , propargyl alcohol , aniline , aryl , substrate (aquarium) , base (topology) , alkyl , medicinal chemistry , solvent , combinatorial chemistry , organic chemistry , stereochemistry , catalysis , mathematical analysis , oceanography , mathematics , geology
This study presents an efficient procedure for synthesis of 3,4,5‐trisubstituted 3 H ‐oxazol‐2‐ones and 3,4‐disubstituted (Z)‐oxazolidin‐2‐ones from substituted propargyl alcohols and aryl/alkyl isocyanates in the presence of LiO t Bu, a base, and DMF, a solvent. This one‐step, low‐cost and gram scale synthesis exhibits superior atom economy, good to excellent yields, enhanced substrate scope and, high functional group tolerance and uses column chromatography‐free purifications. Further, a product containing bromo substituent was successfully examined for Suzuki coupling with a view to amplifying the complexity of the molecule. Finally, the three component (aniline, Di‐tert‐butyldicarbonate and propargyl alcohol) reaction was demonstrated to get the oxazolon‐2‐ones (3 H ‐oxazol‐2‐one and oxazolidin‐2‐one).