An improved synthesis of 2,2-disubstituted-1,2-dihydroquinolines and their conversion to 3-chloro-2,2-disubstituted-tetrahydroquinolines

N-(1,1-disubstitutedpropargyl)anilines can be cyclised to 2,2-disubstituted-1,2-dihydroquinolines by refluxing them in toluene containing cuprous chloride. Electron donating groups in the para position of the ring enhance the reaction rate and electron withdrawing groups markedly decrease the rate....

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Bibliographic Details
Published in:Tetrahedron letters 1995-10, Vol.36 (42), p.7721-7724
Main Authors: Williamson, Natalie M, March, Darren R, David Ward, A
Format: Article
Language:English
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Summary:N-(1,1-disubstitutedpropargyl)anilines can be cyclised to 2,2-disubstituted-1,2-dihydroquinolines by refluxing them in toluene containing cuprous chloride. Electron donating groups in the para position of the ring enhance the reaction rate and electron withdrawing groups markedly decrease the rate. The derived N-acetyldihydroquinolines can be cis dichlorinated and selectively monodechlorinated at the benzylic position to produce 3-chlorotetrahydroquinolines.
ISSN:0040-4039
1873-3581
DOI:10.1016/0040-4039(95)01572-Y