POCl3 mediated one-pot deoxygenative aromatization and electrophilic chlorination of dihydroxy-2-methyl-4-oxo-indeno[1,2-b]pyrroles

A class of indenopyrroles is presented by the treatment of known dihydroxy-2-methyl-4-oxoindeno[1,2-b]pyrroles with phosphorus oxychloride (POCl3). The elimination of vicinal hydroxyl groups at the 3a and 8b positions, formation of a p bond, and electrophilic chlorination of the methyl group attached to C-2 resulted in the fused aromatic pyrrole structures. Benzylic substitution of various nucleophiles such as H2O, EtOH, and NaN3 with a chlorine atom gave diverse 4-oxoindeno[1,2-b]pyrrole derivatives in 58 to 93% yields. The reaction was investigated in different aprotic solvents, and the highest reaction yield was obtained in DMF. The structures of the products were confirmed by spectroscopic methods, elemental analysis, and X-ray crystallography.

Automated summary

A class of indenopyrroles was synthesized by the treatment of dihydroxy-2-methyl-4-oxoindeno[1,2-b]pyrroles with phosphorus oxychloride. The elimination of vicinal hydroxyl groups, formation of a p bond, and electrophilic chlorination produced fused aromatic pyrrole structures. Benzylic substitution of nucleophiles resulted in diverse 4-oxoindeno[1,2-b]pyrrole derivatives with yields of 58-93%. The reaction showed the highest yield when conducted in DMF. The structures of the products were confirmed using spectroscopic methods, elemental analysis, and X-ray crystallography.