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Synthesis 1989; 1989(3): 221-222
DOI: 10.1055/s-1989-27209
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2-Substituted 1,2,3,4-Tetrahydroquinolines from Quinoline

Steven W. Goldstein* , Paul J. Dambek
  • *Pfizer Central Research, Groton, CT 06340, USA
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Publication History

Publication Date:
17 September 2002 (online)

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The addition of various organometallic reagents to quinoline occurred solely at the 2-position of the heteroaromatic ring. The resultant 2-substituted 1,2-dihydroquinolines were then easily reduced with sodium in ethanol to the 1,2,3,4-tetrahydro species. The overall transformation of quinoline to 2-substituted 1,2,3,4-tetrahydroquinolines was found to be favorable to the previous literature conditions, which required an intermediate oxidative step. The yields for the last step ranged from 42-98% but were generally greater than 80%.

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