Document Type : Original Research Article


1 Department of Chemistry, Begum Rokeya University, Rangpur-5400, Bangladesh

2 Department of Chemistry, University of Rajshahi, Rajshahi-6205, Bangladesh

3 Department of Chemistry, Mawlana Bhashani Science and Technology University, Tangail-1902, Bangladesh


Azides are the precursors of two important derivatives in synthetic organic chemistry. Achiral amines are not as demandable as that of chiral ones. Chiral amines and diamines have versatile uses in enantioselective reactions. Both simple and amino alcohols were undergone smooth azidation reaction in the mixture of NaN3, H2SO4 in toluene solvent and afforded good to charming yields. Importantly, optical purity of some chiral amino alcohols was reserved during azidation reaction. This is an efficient method to synthesise new azides for the fabrication of new organocatalyst which is friendly to the environment.

Graphical Abstract

Rapid access of some rare chiral azides from sterically hindered alcohols by green chemistry protocol


Main Subjects

[1]. Kumar H.M.S., Reddy B.V.S., Anjaneyulu S., Yadav J.S. Tetrahedron  Lett., 1999, 40:8305
[2]. Tiemann F., Ber. Dtsch. Chem. Ges., 1891, 24:4162
[3]. Staudinger H., Meyer J. Helv. Chim. Acta., 1919, 2:635
[4]. Mungall W.S., Greene G.L., Heavner G.A., Letsinger R.L. J. Org. Chem., 1975, 40:1659
[5]. Huisgen R. Angew. Chem. Int. Ed. Engl., 1963, 2:565                          
[6]. Muller P., Fruit C. Chem. Rev., 2003, 103:2905
[7]. Gallagher D.J., Wu S., Nikolic N.A., Beak P. J. Org. Chem., 1995, 60:8148
[8]. Beak P., Kerrick S.T., Wu S., Chu J. J. Am. Chem. Soc., 1994, 116:3231                        
[9]. Li X., Schenkel L.B., Kozlowski M. Org. Lett., 2000, 2:875
[10]. Noyori R., Wiley J., Chichester. Wiley Online Library, 1994, 115:155
[11]. Seyden J.P., Wiley J. Applied Organometallic Chemistry, 1997, 11:457
[12]. Oppolzer W., Wills M., Starkemann C., Bernardinelli G., Tetrahedron Lett., 1990, 31:4117                           
[13]. Gibson C.L., La Rosa S., Suckling C.J. Tetrahedron Lett., 2003, 44:1267
[14]. Chehade, K.A.H., Spielmann H.P. J. Org. Chem., 2000, 65:4949
[15]. Miller D.R., Swenson D.C., Gillan E.G. J. Am. Chem. Soc., 2004, 126:5372
[16]. Mitsunobu O. Bull. Chem. Soc. Japan, 1967, 40:4235
[17]. Hughes D.L. Org. React., 1992, 42:335
[18]. Loibner H., Zibral E. Helv. Chim. Acta., 1976, 59:2100
[19]. L'abbé G., Hassner A. Angew. Chem. Int. Ed. Engl., 1971, 10:98
[20]. L'abbé G. Angew. Chem. Int. Ed. Engl., 1975, 14:775
[21]. Soderberg B.C.G. Curr. Org. Chem., 2000, 4:727
How to cite this manuscript: Mohammad Nuruzzaman Khan*, Harendra Nath Roy, Pijush Kanti Roy, Mohammad Motahar Hossain. Rapid access of some rare chiral azides from sterically hindered alcohols by green chemistry protocol.Asian Journal of Green Chemistry, 3(3) 2019, 336-344. DOI: 10.22034/ajgc.2018.140100.1085