A new general method for the synthesis of pyrrole-2,5-dicarbaldehyde and its 3-mono- and 3,4-disubstituted derivatives is reported. It involves the intermediate formation of the corresponding 2,5-bis(1,3-benzodithiol-2-yl)pyrroles followed by hydrolysis with HgO–35% aq. HBF4–DMSO. Pyrrole-2,5-dicarbaldehyde was obtained in overall yields of 43–65%, whilst that of the derivatives was 32–90%. Moreover the methylation of the corresponding dithiolic intermediate with further hydrolysis resulted in the formation of 1-methylpyrrole-2,5-dicarbaldehyde in 90% overall yield
A Convenient General Method for the Synthesis of Pyrrole-2,5-dicarbaldehydes
CADAMURO, Silvano;
1993-01-01
Abstract
A new general method for the synthesis of pyrrole-2,5-dicarbaldehyde and its 3-mono- and 3,4-disubstituted derivatives is reported. It involves the intermediate formation of the corresponding 2,5-bis(1,3-benzodithiol-2-yl)pyrroles followed by hydrolysis with HgO–35% aq. HBF4–DMSO. Pyrrole-2,5-dicarbaldehyde was obtained in overall yields of 43–65%, whilst that of the derivatives was 32–90%. Moreover the methylation of the corresponding dithiolic intermediate with further hydrolysis resulted in the formation of 1-methylpyrrole-2,5-dicarbaldehyde in 90% overall yield
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