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Efficient Synthesis of Tetrahydroquinolines from the Reaction of Aldehyde, Aniline, and Alkene under the In Situ Redox of SnCl 2 and FeCl 3
Author(s) -
Guo Qiaoxia,
Teng Weiling,
Ren Shenyong,
Rao Shasha,
Wang Yanqing,
Chen Liwei,
Shen Baojian,
Takahashi Tamotsu
Publication year - 2014
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.2118
Subject(s) - chemistry , aniline , aldehyde , alkene , redox , medicinal chemistry , in situ , organic chemistry , catalysis
A highly efficient three‐component Povarov reaction for the synthesis of tetrahydroquinoline derivatives was reported. The reaction of aldehyde, aniline, and alkene was carried out in the presence of Sn(IV), which was generated in situ from the redox reaction of SnCl 2 and FeCl 3 , to afford tetrahydroquinoline derivatives in good to excellent yields. This discovery showed a sharp difference from the direct use of unstable SnCl 4 . Both aliphatic and aromatic aldehydes could be applied for the synthesis of the heterocycle in the reaction. The structure of the product 6‐chloro‐4‐methyl‐4‐neopentyl‐2‐propyltetrahydroquinoline and 6‐bromo‐4‐methyl‐4‐neopentyl‐2‐propyltetrahydroquinoline was confirmed by X‐ray diffraction analysis.