Cycloaddition reactions of thiazolium azomethine ylides: application to pyrrolo[2,1-b]thiazoles.
Thiazolium azomethine ylides, equipped with a C-2 methanethiol group, participate in an efficient [3 + 2] cycloaddition reaction with acetylene derivatives to yield unique pyrrolo[2,1-b]thiazoles. The elimination of the methanethiol leaving group from the cycloadduct has replaced the need for a separate oxidation step and suppresses ring-opening side reactions. Products were obtained in short synthetic sequences to demonstrate their use as a scaffold for compound libraries.
Berry
Craig R
CR
Johnson & Johnson Pharmaceutical Research & Development, L.L.C., 8 Clarke Drive, Cranbury, New Jersey 08512, USA.
Zificsak
Craig A
CA
Gibbs
Alan C
AC
Hlasta
Dennis J
DJ
D000480:Alkynes / Q000737:chemistry; D001391:Azo Compounds / Q000737:chemistry*; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D015394:Molecular Structure; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D013844:Thiazoles / Q000138:chemical synthesis* / Q000737:chemistry*; D013882:Thiosemicarbazones / Q000737:chemistry*
D000480:Alkynes; D001391:Azo Compounds; D011758:Pyrroles; D013844:Thiazoles; D013882:Thiosemicarbazones; C512188:azomethine