Terminal Organylchalcogenoethyl- and -propylamines and Their Schiff Base Derivatives

Svetlana V. Amosova; Natalia A. Makhaeva; Alexander V. Martynov; Vladimir A. Potapov; Barry R. Steele; Ioannis D. Kostas

doi:10.1055/s-2005-865310

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Synthesis 2005(10): 1641-1648
DOI: 10.1055/s-2005-865310

PAPER

Terminal Organylchalcogenoethyl- and -propylamines and Their Schiff Base Derivatives

Svetlana V. Amosova*^a, Natalia A. Makhaeva^a, Alexander V. Martynov^a, Vladimir A. Potapov^a, Barry R. Steele^b, Ioannis D. Kostas^b
^a A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1, Favorsky Str., Irkutsk 664033, Russia
Fax: +7(3952)425885; e-Mail: amosova@irioch.irk.ru;
^b National Hellenic Research Foundation, Institute of Organic and Pharmaceutical Chemistry, Vas. Constantinou 48, 11635 Athens, Greece

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Publication History

Received 17 November 2004
Publication Date:
12 April 2005 (online)

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Abstract

A series of organoselanyl- and organotellanyl-substituted ethyl- and propylamines and their hydrochlorides, as well as 2-(methylsulfanyl)ethylamine have been synthesized. Efficient general synthetic routes have been developed to chalcogen(S, Se, Te)-containing Schiff bases with di- and trimethylene bridges between the nitrogen atom of the imino group and the chalcogen, by condensation of 3-(tert-butyl)- and 3-(1-ethylpropyl)-2-hydoxybenzene-carbaldehydes with the amines. The influence of the organylchalcogenyl-group on some spectral characteristics (¹H, ¹³C, ⁷⁷Se NMR spectroscopy) of both amines and Schiff bases is discussed.

Key words

amines - Schiff bases - condensation - spectroscopy - organometallic reagents

References

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Initial investigations have been carried out with Schiff bases 11a and 11b which readily form stable complexes on reaction with Li₂PdCl₄. These complexes are now being investigated as catalysts for cross-coupling reactions and encouraging preliminary results have so far been obtained for the Suzuki reaction. This work is now being actively pursued and will be reported in due course.