Abstract
A practical and simple method that allows preparation of azides from alcohols is described. The process involves oxyphosphonium-type activation and it is based upon the use of nicotinoyl azide (NCA), a cheap and easily accessible azide ion source.
Key words
azides - alcohols - nicotinoyl azide (NCA)
References
1a Zhang S.
Reith MEA.
Dutta AK.
Bioorg. Med. Chem. Lett.
2003,
13:
1591
1b Deng W.-P.
Nam G.
Fan J.
Kirk KL.
J. Org. Chem.
2003,
68:
2798
1c Jung YJ.
Chang YM.
Lee JH.
Yoon CM.
Tetrahedron Lett.
2002,
38:
8735
2a Meyer J.
Helv. Chim. Acta
1919,
2:
635
2b Michellizza S.
Al-Mourabit A.
Gateau-Olesker A.
Marazano C.
J. Org. Chem.
2002,
67:
6474
2c Battaglia A.
Barbaro G.
Giorgianni P.
Guerrini A.
Pepe A.
Tetrahedron: Asymmetry
2001,
12:
1015
3a Scriven EFV.
Azides and Nitrenes
Academic Press;
New York:
1984.
3b Stevens TS.
Watts WE.
Selected Molecular Rearrangements
Van Nostrand Reinhold;
London:
1973.
4a Katritzky A.
Singh SK.
J. Org. Chem.
2002,
67:
9077
4b Trauner D.
Porth S.
Opatz T.
Bats JW.
Geister G.
Multzer J.
Synthesis
1998,
653
4c Schultz AG.
Dai M.
Kim SK.
Pettus L.
Thakhar K.
Tetrahedron Lett.
1998,
39:
4203
4d Kolb HC.
Sharpless B.
Drug Discov. Today
2003,
8:
1128
5 Stork G.
Niu D.
Fujimoto A.
Koft ER.
Balkovec JM.
Tata JR.
Dake GR.
J. Am. Chem. Soc.
2001,
123:
3239
6a Schildknegt K.
Agrios KA.
Aubé J.
Tetrahedron Lett.
1998,
39:
7687
6b Milligan GL.
Mossman CJ.
Aubé J.
J. Am. Chem. Soc.
1995,
117:
10449
7 Ito M.
Koyakumaru K.-I.
Ohta T.
Takaya H.
Synthesis
1995,
376
8a Biffin MEC.
Miller J.
Paul DB. In The Chemistry of the Azido Group
Patai S. Wiley Interscience;
New York:
1971.
p.57
8b Alvarez SG.
Alvarez MT.
Synthesis
1997,
413
9a Vatèle JM.
Hanessian S.
Tetrahedron
1996,
52:
10557
9b Vatèle JM.
Hanessian S.
Tetrahedron Lett.
1981,
22:
3579
10a Mitsunobu O.
Synthesis
1981,
1
10b Hughes DL.
Org. React.
1992,
42:
335
11a Loibner H.
Zbiral E.
Helv. Chim. Acta
1976,
59:
2100
11b Chen C.-P.
Prasad K.
Repic O.
Tetrahedron Lett.
1991,
32:
7175
12 Viaud MC.
Rollin P.
Synthesis
1990,
130
13 Lal B.
Pramanik BN.
Manhas MS.
Bose AK.
Tetrahedron Lett.
1977,
23:
1977
14 He L.
Wanunu M.
Byun H.-S.
Bittman R.
J. Org. Chem.
1999,
64:
6049
15 Firouzabadi H.
Iranpoor N.
Sobhani S.
Tetrahedron
2004,
60:
203
16 Iranpoor N.
Firouzabadi H.
Akhlaghinia B.
Nowrouzi N.
Tetrahedron Lett.
2004,
45:
3291
17 Thompson AS.
Humphrey GR.
DeMarco AM.
Mathre DJ.
Grabowski EJJ.
J. Org. Chem.
1993,
58:
5886
18 Mizuno M.
Shioiri T.
Chem. Commun.
1997,
2165
19 Satish Kumar N.
Praveen Kumar K.
Pavan Kumar KVP.
Praveen K.
Vittal JJ.
Swamy Kumara KC.
J. Org. Chem.
2004,
69:
1880
20 Froeyen P.
Phosphorous, Sulfur, Silicon Relat. Elem.
1993,
78:
161
21 Breslow DS.
J. Am. Chem. Soc.
1950,
72:
4244
22 Halgren TA.
J. Computational Chem.
1996,
17:
490
23 DSC (Mettler-Toledo Star® System, heating rate: 10 °C min-1 ): endothermic effect between 40 °C and 66 °C (melting of the reagent, ΔHendo = 106 J g-1 ); exothermic effect between 73 °C and 151 °C (Schmidt rearrangement plus decomposition, ΔHexo = 1051 J g-1 ).
24a Iyengar BS.
Dorr RT.
Alberts DS.
Hersh EM.
Salmon SE.
Remers W.
J. Med. Chem.
1999,
42:
510
24b L’Abbe G.
Synthesis
1987,
525
25 Casimiro-Garcia A.
Clercq ED.
Pannecoque C.
Witvrouw M.
Stup TL.
Bioorg. Med. Chem.
2000,
8:
197
26 Freiberg LA.
J. Org. Chem.
1965,
30:
2476
27a Gòmez-Vidal JA.
Silverman RB.
Org. Lett.
2001,
3:
2481
27b Marusawa H.
Setoi H.
Sadawa A.
Kuroda A.
Seki J.
Motoyama Y.
Tanaka H.
Bioorg. Med. Chem.
2002,
10:
1399
28a Finke PE.
Oates B.
Sanders MG.
MacCoss M.
Malkowitz L.
Springer MS.
Gould SL.
DeMartino JA.
Carella A.
Carver G.
Holmes K.
Bioorg. Med. Chem.
2001,
11:
2475
28b Moore KW.
Bonner K.
Jones EA.
Emms F.
Leeson PD.
Bioorg. Med. Chem.
1999,
9:
1285
29 Ito M.
Koyakumaru K.
Otha T.
Takaya H.
Synthesis
1995,
4:
376
30a Kevill DN.
Weitl FL.
J. Org. Chem.
1970,
35:
2526
30b Sasaki T.
Eguchi S.
Katada T.
Hiroaki O.
J. Org. Chem.
1977,
42:
3741
31 Mark E.
Zbiral E.
Monatsh. Chem.
1981,
112:
215
32a Shea KJ.
Tetrahedron
1980,
363:
1683
32b Warner PM.
Chem. Rev.
1989,
89:
1067
32c Billups WE.
Haley MM.
Lee G.
Chem. Rev.
1989,
89:
1147
33a Barret IC.
Kerr MA.
Synlett
2000,
11:
1673
33b Hassner A.
Stern M.
Angew. Chem.
1986,
98:
479
34 Sampath Kumar HM.
Reddy BVS.
Anjaneyulu S.
Yadav JS.
Tetrahedron Lett.
1998,
39:
7385
35 Occhiato E.
Jones JB.
Tetrahedron
1996,
52:
4199
36a Tao L.
Wang Y.-G.
Ma C.
Zheng B.
Chen Y.-Z.
Synth. Commun.
1999,
29:
2053
36b Xu H.
Zhang X.
Tian X.
Lu M.
Wang Y.-G.
Chem. Pharm. Bull.
2002,
50:
399
37 Kanai T.
Kanagawa Y.
Ishii Y.
J. Org. Chem.
1990,
55:
3274
38 Malkov AV.
Spoor P.
Vinader V.
Kocovsky P.
J. Org. Chem.
1999,
64:
5308
39a Murahashi S.-I.
Taniguchi Y.
Imada Y.
Tanigawaq Y.
J. Org. Chem.
1989,
54:
3292
39b Murahashi S.-I.
Taniguchi Y.
Imada Y.
Tanigawaq Y.
Tetrahedron Lett.
1986,
27:
227
39c Varma RS.
Naicker KP.
Tetrahedron Lett.
1998,
39:
2915
40 Varasi M.
Walker KAM.
Maddox ML.
J. Org. Chem.
1987,
52:
4235
41 Afonso CM.
Barros MT.
Godinho LS.
Maycock CD.
Tetrahedron
1994,
50:
9671
42
1 H NMR (300 MHz, CDCl3 ): δ = 1.24-1.31 (m, 6 H), 4.15-4.27 (m, 4 H), 7.35-7.42 (m, 1 H), 7.96-7.98 (d, J = 7.6 Hz, 1 H), 8.71-8.73 (d, J = 5 Hz, 1 H), 8.86 (s, 1 H). MS m/z = 282.26 (MH+ ).
