Synthesis of N-Sulfonyl Amidines and Acyl Sulfonyl Ureas from Sulfonyl Azides, Carbon Monoxide, and Amides.
A Pd-catalyzed and ligand-free carbonylation/cycloaddition/decarboxylation cascade synthesis of sulfonyl amidines from sulfonyl azides and substituted amides at low CO pressure is reported. The reaction proceeds via an initial Pd-catalyzed carbonylative generation of sulfonyl isocyanates from sulfonyl azides, followed by a [2 + 2] cycloaddition with amides and subsequent decarboxylation, which liberates the desired sulfonyl amidines, generating N2and CO2as the only reaction byproducts. Using this simple protocol, a diverse range of sulfonyl amidines was obtained in moderate to excellent yields. In addition, the reaction can also be directed through a more conventional amidocarbonylation pathway by employing N-monosubstituted amide nucleophiles to afford acyl sulfonyl ureas in good yields.
Organic Pharmaceutical Chemistry, Department of Medicinal Chemistry, Uppsala Biomedical Center, Uppsala University , P.O. Box 574, SE-751 23 Uppsala, Sweden.
Shiao Y
SY
Chow
Organic Pharmaceutical Chemistry, Department of Medicinal Chemistry, Uppsala Biomedical Center, Uppsala University , P.O. Box 574, SE-751 23 Uppsala, Sweden.
Luke R
0000-0001-7658-5103
LR
Odell
D000577:Amides / Q000737:chemistry*; D000578:Amidines / Q000138:chemical synthesis*; D001386:Azides / Q000737:chemistry*; D002248:Carbon Monoxide / Q000737:chemistry*; D061565:Cycloaddition Reaction; D013057:Spectrum Analysis / Q000379:methods; D013450:Sulfones / Q000737:chemistry*; D014508:Urea / Q000138:chemical synthesis* / Q000737:chemistry
D000577:Amides; D000578:Amidines; D001386:Azides; D013450:Sulfones; D002248:Carbon Monoxide; D014508:Urea