Letter | Published:

A New Synthesis of 2 : 7-Disubstituted-1 : 2 : 3 : 4-tetrahydro-iso-quinolines

Nature volume 162, pages 337338 (28 August 1948) | Download Citation

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Abstract

IT has been shown by Holliman and Mann1 that o-2-bromoethyl-benzyl bromide (I) condenses readily with primary amines to give 2-substituted-1 : 2 : 3 : 4-tetrahydro-iso-quinolines (II). Although hitherto this has apparently been the only known method for the synthesis of 2-aryl-iso-quinolines of type (II), it has one serious disadvantage, namely, that for various reasons it does not lend itself to the preparation of iso-quinolines of this type having substituent groups in the benzene ring. The presence of such groups may be essential if the tetrahydro-iso-quinoline is to possess marked physiological action. To overcome this difficulty we have developed the following synthesis.

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References

  1. 1.

    and , J. Chem. Soc., 34 (1945).

  2. 2.

    , J. Chem. Soc., 95, 2193 (1909).

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Author information

Affiliations

  1. University Chemical Laboratory, Cambridge.

    • F. G. MANN
    •  & M. H. BEEBY

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DOI

https://doi.org/10.1038/162337b0

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