Abstract
Closure of the pyridine ring in the Combes quinoline synthesis occurs by a type of intramolecular electrophilic substitution. With two free ortho positions the direction of ring formation depends both on the initial electrophilic attack, i.e., the nucleophilicity of the ortho carbon atom, and on the possibility of stabilizing the intermediate complex. The steric requirements of substituents both in the enaminoketone chain and in the position ortho to the point of attack exert a significant effect on the direction of ring closure. The steric factor is decisive when forming condensed angular quinoline structures.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1011–1024, August, 1992.
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Yamashkin, S.A., Yudin, L.G. & Kost, A.N. Closure of the pyridine ring in the combes quinoline synthesis (Review). Chem Heterocycl Compd 28, 845–855 (1992). https://doi.org/10.1007/BF00531313
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DOI: https://doi.org/10.1007/BF00531313