Cyclic thioanhydrides: linchpins for multicomponent coupling reactions based on the reaction of thioacids with electron-deficient sulfonamides and azides.
Reaction of cyclic thioanhydrides with amines affords amides functionalized with thioacids, which can be trapped in situ with electron-deficient azides or, preferably, 2,4-dinitrobenzenesulfonamides. In this manner the cyclic thioanhydride serves as a linchpin in a three-component coupling sequence. The use of thiomaleic anhydride and a bifunctional nucleophile extends the process to heterocycle synthesis, while a cyclic thioanhydride prepared from aspartic acid directly provides N-functionalized asparagine derivatives.
Crich
David
D
Department of Chemistry, Wayne State University, 5101 Cass Avenue, Detroit, Michigan 48230, USA. Dcrich@chem.wayne.edu
Bowers
Albert A
AA
D000143:Acids / Q000737:chemistry*; D000588:Amines / Q000737:chemistry; D000812:Anhydrides / Q000138:chemical synthesis* / Q000737:chemistry; D001216:Asparagine / Q000138:chemical synthesis / Q000737:chemistry; D001386:Azides / Q000737:chemistry*; D004583:Electrons; D047028:Macrocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009578:Nitrobenzenes / Q000737:chemistry; D013438:Sulfhydryl Compounds / Q000737:chemistry*; D013449:Sulfonamides / Q000737:chemistry*
D000143:Acids; D000588:Amines; D000812:Anhydrides; D001386:Azides; D047028:Macrocyclic Compounds; D009578:Nitrobenzenes; D013438:Sulfhydryl Compounds; D013449:Sulfonamides; D001216:Asparagine; C036077:nitrobenzene