Phosphorus, Sulfur, and Silicon, 179:1813–1817, 2004
ꢀC
Copyright Taylor & Francis Inc.
ISSN: 1042-6507 print / 1563-5325 online
DOI: 10.1080/10426500490466544
CHEMOSELECTIVE REDUCTION OF AZIDES WITH
SODIUM SULFIDE HYDRATE UNDER SOLVENT
FREE CONDITIONS
Foad Kazemi, Ali Reza Kiasat, and Sohyl Sayyahi
Chemistry Department, College of Science, Shahid Chamran
University, Ahvaz, Iran
(Received January 22, 2004)
Sodium sulfide hydrate has been employed for an efficient reduction of a
variety of azides to the primary amines in good-to-excellent yields under
solvent-free system and without perturbing many active functionalities
such as ether, carbonyl, sulfonyl, and nitro.
Keywords: Azides; reduction; sodium sulfide; solvent free
Primary amines have widely been recognized as an important class
of compounds due in part to their role as intermediates in organic
synthesis, such as in the preparation of nitrogen containing hetero-
cycles, carbohydrates, and in nucleoside chemistry.1 In addition, it is
known that many of the primary amines are biologically active com-
pounds or are the important building blocks for the syntheses of bio-
logically active compounds.2 Of the several methods to prepare amines,
reduction of azides is of immense importance. Since numerous meth-
ods are available for the preparation of azides with excellent regio-,
stereo-, and enantioselectivity, the reduction of azides permits a con-
trolled introduction of amine functionality.3 A number of reagents
have been described in the literature4 for this reductive process
which includes lithium aluminum hydride,5 borohydrides,6 diborane,7
triphenylphosphine,8 benzyltriethylammonium tetrathiomolymbdate,9
hexamethyl-disilathiane,10 samarium iodide,11 etc. In terms of practi-
cal applicability, selectivity, toxicity, reaction conditions, or commer-
cial availability, most of these methods have some disadvantages. For
Authors acknowledge the partial support of this work by Shahid Chamran Ahvaz
University Research Council.
Address correspondence to Foad Kazemi, Chemistry Department, College of Science,
Shahid Chamran University, Ahvaz 6137-4-3169, Iran.
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