Reduction of azides to amines with 1,3-Propanedithiol
Organic azides are versatile nitrogen intermediates in organic and bio-chemistry and their transformation into amines provides a broad scope of applications. [1] In this context, sulfur reagents have proved to be very useful in a wide range of azide reductions as presented in the Scheme below. In a scalable synthesis of stable isotope labeled Sphingomyelins, the azide is reduced to the corresponding amine using a combination of 1,3-propanedithiol and Et?N in methanol. [2]
The mechanism of reduction of an azido group by a dithiol has been studied. [3]
[1] For comprehensive information about azide chemistry, see: (a) E. F. V. Scriven, K. Turnbull, Chem. Rev. 1988, 88, 297-368. (b) S. Br?se, C. Gil, K. Knepper, V. Zimmermann, Angew. Chem. Int. Ed. 2005, 44, 5188-5240.
[2] N. Philippe, S. Pérard, F. Le Strat, J. Blankenstein, S. Roy, Synthesis 2020, 52, 2106-2110.
[3] I. L. Cartwright, D. W. Hutchinson, V. W. Armstrong, Nucleic Acids Res. 1976, 3, 2331-2339.
Professor at Monastir University
1 天前Congratulations. Very interesting
Visiting Lecturer(chemistry). Seeking PhD admission, and University based Research Assistant, visiting Faculty, and Lab chemist Position,
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Associate Director, Medicinal Chemistry, SynVent IDD, Syngene
2 周1,3-Propanedithiol, only for the chemists who know how to handle the stink. An excellent, clean method though. Tried and tested!
Professeur de l'Enseignement Supérieur chez Université Sultan My Slimane, Béni-Mellal
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