Chemical and Pharmaceutical Bulletin p. 1269 - 1275 (1999)
Update date:2022-09-26
Topics:
Toda, Jun
Sakagami, Michiya
Sano, Takehiro
A synthesis of 1,2,3,4-tetrahydroquinolines (TQs) 13 with two and three methoxyl groups on the benzene ring, was achieved via intramolecular cyclization of N-aryl-N-[(phenylsulfinyl)propyl]formamides 7 utilizing the Pummerer reaction as a key step. The reaction was carried out by using trifluoroacetic anhydride (TFAA) (method A) or TFAA-BF3 · Et2O (method B). The cyclization to 4-PhSTQs 8 proceeded effectively when the reaction center at the benzene ring was electronically activated by a methoxyl group. In the reaction of sulfoxide 7e having two OMe groups in the ortho- and para- positions, a different cyclization reaction leading to 1,5-benzothiazepine derivative 9 was observed, indicating that the high nucleophilicity of the benzene ring caused the unexpected reaction prior to cyclization to 4-PhSTQs 8. This route starting from methoxyanilines provides an efficient and convenient method of TQ synthesis.
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Doi:10.1021/jo990644t
(1999)Doi:10.1007/BF02495309
(1999)Doi:10.1021/ol991040e
(1999)Doi:10.1039/c6gc02003h
(2017)Doi:10.1021/jo051491e
(2005)Doi:10.1016/S0040-4020(01)90984-6
(1968)
