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Issue 24, 2000
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On the coupling of aryldiazonium salts with N,N-disubstituted 2-aminothiophenes and some of their carbocyclic and heterocyclic analogues

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Abstract

As exemplified with the morpholino derivatives 7, N,N-disubstituted 2-aminothiophenes couple, depending on the substitution pattern at C(5), with aryldiazonium salts 1 either at their C(3) or C(5) position yielding the corresponding 3-arylazo-2-morpholinothiophenes 9 or, under elimination of the substituent at C(5), 5-arylazo-2-morpholinothiophenes 10. This reaction contrasts to the behaviour of 5-morpholinothiazoles 8 and dimethylaniline 13 towards the same diazonium salts 1 which are unable to couple with these compounds if their C(5) or C(4) position, respectively, is not substituted by H, COOH or CHO.

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Publication details

The article was received on 21 Aug 2000, accepted on 27 Sep 2000 and first published on 21 Nov 2000


Article type: Paper
DOI: 10.1039/B006803I
J. Chem. Soc., Perkin Trans. 1, 2000, 4316-4320

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    On the coupling of aryldiazonium salts with N,N-disubstituted 2-aminothiophenes and some of their carbocyclic and heterocyclic analogues

    H. Hartmann and I. Zug, J. Chem. Soc., Perkin Trans. 1, 2000, 4316
    DOI: 10.1039/B006803I

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