Organic Azides || Synthesis of Azides

✍ Scribed by Brse, Stefan; Banert, Klaus

• Publisher: John Wiley & Sons, Ltd
• Year: 2009
• Tongue: English
• Weight: 520 KB
• Edition: 1
• Category: Article
• ISBN: 0470519983
• DOI: 10.1002/9780470682517.ch3

✦ Synopsis

The chemistry of azides starts with the preparation of the fi rst organic azide, phenyl azide, by Peter Griess in 1864 1 and with the discovery of hydrogen azide and the rearrangement of acyl azides to the corresponding isocyanate reported by Curtius in 1890 (Curtius rearrangement). 2 However, only in the 1950s and 1960s did organic azides receive considerable attention pushed by the reviews of Smith 3 and Boyer et al. 4 on the chemistry of the acyl, aryl, and alkyl azides.

Since then numerous syntheses and applications of organic azides have been developed. 5 These energy -rich molecules became valuable intermediates in organic synthesis, in particular in the synthesis of various nitrogen -containing heterocycles, in peptide chemistry and in combinatorial chemistry. They found application as blowing agents and as pharmaceuticals. It is worthwhile to mention the international interest on azidonucleosides in the treatment of AIDS 6 and their application for the preparation of bioconjugates via Staudinger ligation. 7 Here an overview is provided of the more relevant synthetic methods for the preparation of organic azides.