Abstract
Beckmann rearrangement was used as a key step to synthesize six-membered lactams fused to a heteroaromatic or aromatic system. Derivatives of biologically active scaffolds like β- and γ- carbolinone, dihydropyrrolopyridinone and tetrahydroisoquinolinone were synthesized using this strategy.
Highlights
Since the discovery of this Beckmann rearrangement (BR) in 1896, successive investigations have been largely carried out and applied in many ways
The work started with the synthesis of β- and γ-carbolinones
The synthesis of two β-carbolinone, three new γ-carbolinone, new pyrrolopyridinone and tetrahydroisoquinolinone derivatives was achieved in good to moderate yields
Summary
Since the discovery of this Beckmann rearrangement (BR) in 1896, successive investigations have been largely carried out and applied in many ways. To a solution of 4- methyl1,2-dihydrocyclopenta[b]indol-3(4H)-one (0.64 g, 0.0032 mol) in methanol (20 mL), hydroxylamine hydrochloride (0.9 g, 0.013 mol) and (1.0 mL, 0.013 mol) of pyridine were added, the reaction mixture was heated on water bath for 10 hours.
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