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 / S. CADAMURO; IACOPO DEGANI; RITA FOCHI; ANTONELLA GATTI; LAURA PISCOPO. - In: JOURNAL OF THE CHEMICAL SOCIETY. PERKIN TRANSACTIONS. I. - ISSN 0300-922X. - 23(1993), pp. 2939-2943.

A Convenient General Method for the Synthesis of Pyrrole-2,5-dicarbaldehydes

CADAMURO, Silvano;
1993

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
23
2939
2943
pyrrole-2; 5-dicarbaldehyde 2; 5-bis(1; 3-benzodithiol-2-yl)pyrroles
S. CADAMURO; IACOPO DEGANI; RITA FOCHI; ANTONELLA GATTI; LAURA PISCOPO
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2318/3293
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