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Paper | Special issue | Vol 103, No. 2, 2021, pp.723-753
Published online, 20th October, 2020
DOI: 10.3987/COM-20-S(K)31
Mn(III)-Based Oxidative Cyclization of 2-((2-Arylamino)ethyl)malonates: Synthesis of Quinolines via Dihydroquinolinedicarboxylates

Takayuki Nagashimada, Masahiro Morikawa, Kengo Ohki, and Hiroshi Nishino*

*Department of Chemistry, Graduate School of Science, Kumamoto University, Kurokami 2-39-1, Kumamoto 860-8555, Japan


The synthesis of quinolines from aniline derivatives via the Mn(III)-based oxidative cyclization of 2-(2-(arylamino)ethyl)malonates is described. The 2-(2-(arylamino)ethyl)malonates were prepared in two steps from the substituted anilines. The cyclization of nineteen arylaminoethylmalonates protected by the N-acyl and N-alkoxycarbonyl groups easily proceeded in the formal 6-endo mode regardless of the presence of halo, methyl, and methoxy groups on the aromatic ring, and the corresponding tetrahydroquinolinedicarboxylates were produced in high yields except for the 2,4-dimethoxyphenyl-substituted aminoethylmalonate which occurred by ipso-cyclization. The tetrahydroquinolinedicarboxylate could be transformed into quinoline via decarboxylation and deprotective hydrolysis. The characteristic phenomenon in the NMR spectrum of the tetrahydroquinolinedicarboxylates is also discussed.