A class of indenopyrroles is presented by the treatment of known dihydroxy-2-methyl-4-oxoindeno[1,2-]pyrroles with phosphorus oxychloride (POCl). The elimination of vicinal hydroxyl groups at the 3a and 8b positions, formation of a π bond, and electrophilic chlorination of the methyl group attached to C resulted in the fused aromatic pyrrole structures. Benzylic substitution of various nucleophiles such as HO, EtOH, and NaN with a chlorine atom gave diverse 4-oxoindeno[1,2-]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.
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| http://dx.doi.org/10.1039/d3ra02515b | DOI Listing |
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