Abstract
2-Alkenyloxycarbonyl azides 1 and 2-alkynyloxycarbonyl azides 3 undergo in the presence of trimethylsilyl chloride and catalytic amounts of FeCl2 an intramolecular chloroamination (aminochlorination) reaction (Procedure 1). The corresponding oxazolidinones 2 and 4 are formed in moderate to excellent yields (47-99%). The same reagent combination can be employed to convert azides 6 of γ,δ-unsaturated carboxylic acids into the corresponding lactams 7 . The latter reaction is best conducted as a one-pot reaction (Procedure 2) starting from the acids 5 without isolation of the corresponding azides (57-75% yield).
Key words
aminations - chloroaminations - chlorolactamizations - homogenous catalysis - iron - radical reactions
References 1 Present address: Degussa (China) Co., Ltd., 55 Chundong Road, Xinzhuang Industry Park, Shanghai 201108, P.R. China.
2 Present address: LANXESS Fine Chemicals, LXS-FCH-RD-LP2, Geb. Q18, R 304, 51369 Leverkusen, Germany.
3a Kemp JEG. In Comprehensive Organic Synthesis
Vol. 7:
Trost BM.
Fleming I.
Pergamon;
Oxford:
1991.
p.469
3b Mackiewicz P.
Furstoss R.
Tetrahedron
1978,
34:
3241
3c Minisci F.
Acc. Chem. Res.
1975,
8:
165
3d Kovacic P.
Lowery MK.
Field KW.
Chem. Rev.
1970,
70:
639
4a Stella L. In Radicals in Organic Synthesis
Vol. 2:
Renaud P.
Sibi MP.
Wiley-VCH;
Weinheim:
2001.
p.407
4b Fallis AG.
Brinza IM.
Tetrahedron
1997,
53:
17543
4c Esker JL.
Newcomb M.
Adv. Heterocycl. Chem.
1993,
58:
1
4d Cardilllo G.
Orena M.
Tetrahedron
1990,
46:
3321
4e Stella L.
Angew. Chem., Int. Ed. Engl.
1983,
22:
337
5a Kuehne ME.
Horne DA.
J. Org. Chem.
1975,
40:
1287
5b Mackiewicz P.
Furstoss R.
Waegell B.
Cote R.
Lessard J.
J. Org. Chem.
1978,
43:
3746
5c Chow YL.
Perry RA.
Can. J. Chem.
1985,
63:
2203
5d Daoust B.
Lessard J.
Tetrahedron
1999,
55:
3495
5e Sjöholm Å.
Hemmerling M.
Pradeille N.
Somfai P.
J. Chem. Soc., Perkin Trans. 1
2001,
891
5f Noack M.
Kalsow S.
Göttlich R.
Synlett
2004,
1110
6a Foglia TA.
Swern D.
J. Org. Chem.
1966,
31:
3625
6b Schrage K.
Tetrahedron
1967,
23:
3033
6c Schrage K.
Tetrahedron
1967,
23:
3039
6d Daniher FA.
Butler PE.
J. Org. Chem.
1968,
33:
2637
6e Neale RS.
Synthesis
1971,
1
6f Touchard D.
Lessard J.
Tetrahedron Lett.
1971,
4425
6g Barlow MG.
Fleming GL.
Haszeldine RN.
Tipping AE.
J. Chem. Soc. C
1971,
2744
6h Akasaka T.
Furukawa N.
Oae S.
J. Chem. Soc., Perkin Trans. 1
1980,
1257
6i Lessard J.
Mondon M.
Touchard D.
Can. J. Chem.
1981,
59:
431
6j Carpino LA.
Lee S.-N.
J. Org. Chem.
1983,
48:
746
6k Orlek BS.
Stemp G.
Tetrahedron Lett.
1991,
32:
4045
6l Nagao Y.
Katagiri S.
Chem. Lett.
1992,
2379
6m Tsuritani T.
Shinokubo H.
Oshima K.
J. Org. Chem.
2003,
68:
3246
7a Minisci F.
Synthesis
1973,
1
7b Driguez H.
Lessard J.
Can J. Chem.
1977,
55:
720
7c Borch RF.
Evans AJ.
Wade JJ.
J. Am. Chem. Soc.
1977,
99:
1612
7d Lessard J.
Cote R.
Mackiewicz P.
Furstoss R.
Waegell B.
J. Org. Chem.
1978,
43:
3750
7e Stella L.
Raynier B.
Surzur JM.
Tetrahedron
1981,
37:
2843
7f Bougeois J.-L.
Stella L.
Surzur J.-M.
Tetrahedron Lett.
1981,
22:
61
7g Göttlich R.
Synthesis
2000,
1561
7h Wei H.-X.
Kim SH.
Li G.
Tetrahedron
2001,
57:
3869
7i Chen D.
Timmons C.
Chao S.
Li G.
Eur. J. Org. Chem.
2004,
3097
7j Manzoni MR.
Zabawa TP.
Kasi D.
Chemler SR.
Organometallics
2004,
23:
5618
CAUTION! BocN3 is potentially explosive upon heating, see:
8a Koppel HC.
Chem. Eng. News
1976,
54 (39):
5
8b Feyen P.
Angew. Chem., Int. Ed. Engl.
1977,
16:
115
9 Bolm C.
Legros J.
Le Paih J.
Zani L.
Chem. Rev.
2004,
104.:
6217
10a Bach T.
Körber C.
Tetrahedron Lett.
1998,
39:
5015
10b Bach T.
Körber C.
Eur. J. Org. Chem.
1999,
1033
10c Bach T.
Körber C.
J. Org. Chem.
2000,
65:
2358
11a Bolm C.
Muòiz K.
Aguilar N.
Kesselgruber M.
Raabe G.
Synthesis
1999,
1251
11b Gais H.-J.
Loo R.
Roder D.
Das P.
Raabe G.
Eur. J. Org. Chem.
2003,
1500
11c Bacci JP.
Greenman KL.
Van Vranken DL.
J. Org. Chem.
2003,
68:
4955
11d Koep S.
Gais H.-J.
Raabe G.
J. Am. Chem. Soc.
2003,
125:
13243
11e Gais H.-J.
Reddy LR.
Babu GS.
Raabe G.
J. Am. Chem. Soc.
2004,
126:
4859
11f Gais H.-J.
Babu GS.
Günter M.
Das P.
Eur. J. Org. Chem.
2004,
1464
12 Tamura Y.
Uchida T.
Katsuki T.
Tetrahedron Lett.
2003,
44:
3301
13a Körber C.
Ph.D. Thesis
Philipps-Universität Marburg;
Marburg:
1999.
13b Schlummer B.
Ph.D. Thesis
Philipps-Universität Marburg;
Marburg:
2000.
14 Bergmeier SC.
Stanchina DM.
J. Org. Chem.
1997,
62:
4449
15a Bach T.
Schlummer B.
Harms K.
Chem. Commun.
2000,
287
15b Bach T.
Schlummer B.
Harms K.
Chem. Eur. J.
2001,
7:
2581
16a Churchill DG.
Rojas CM.
Tetrahedron Lett.
2002,
43:
7225
16b Chung HW.
Lee GS.
Chung BY.
Bull. Korean Chem. Soc.
2002,
23:
1325
17 Bach T.
Schlummer B.
Harms K.
Synlett
2000,
1330
18 Klügge J.
Herdtweck E.
Bach T.
Synlett
2004,
1199
19a Biloski AJ.
Wood RD.
Ganem B.
J. Am. Chem. Soc.
1982,
104:
3233
19b Rajendra G.
Miller MJ.
J. Org. Chem.
1987,
52:
4471
19c Balko TW.
Brinkmeyer RS.
Terando NH.
Tetrahedron Lett.
1989,
30:
2045
19d Harris NV.
Smith C.
Ashton MJ.
Bridge AW.
Bush RC.
Coffee ECJ.
Dron DI.
Hapter MF.
Lythgoe DJ.
Newton CG.
Riddell D.
J. Med. Chem.
1992,
35:
4384
19e Arunachalam T.
Fan H.
Pillai KMR.
Ranganathan RS.
J. Org. Chem.
1995,
60:
4428
19f Boeckman RK.
Connell BT.
J. Am. Chem. Soc.
1995,
117:
12368
19g Kitagawa O.
Fujita M.
Li H.
Taguchi T.
Tetrahedron Lett.
1997,
38:
615
19h Fujita M.
Kitagawa O.
Suzuki T.
Taguchi T.
J. Org. Chem.
1997,
62:
7330
19i Homsi F.
Rousseau G.
J. Org. Chem.
1999,
64:
81
19j Sudau A.
Münch W.
Nubbemeyer U.
Bats JW.
J. Org. Chem.
2000,
65:
1710
19k Shen M.
Li C.
J. Org. Chem.
2004,
69:
7906
20a Knapp S.
Rodriques KE.
Levorse AT.
Ornaf RM.
Tetrahedron Lett.
1985,
26:
1803
20b Knapp S.
Levorse AT.
J. Org. Chem.
1988,
53:
4006
20c Kurth MJ.
Bloom SH.
J. Org. Chem.
1989,
54:
411
20d Takahata H.
Yamazaki K.
Takamatsu T.
Yamazaki T.
Momose T.
J. Org. Chem.
1990,
55:
3947
21a Phan XT.
Shannon PJ.
J. Org. Chem.
1983,
48:
5164
21b Schulte-Wülwer IA.
Helaja J.
Göttlich R.
Synthesis
2003,
1886
22 Danielec H.
Projected Ph.D. Thesis
Technische Universität München;
München:
2006.
23 Berrisford DJ.
Bolm C.
Sharpless KB.
Angew. Chem., Int. Ed. Engl.
1995,
34:
1059
24 Schlummer B.
Harms K.
Bach T.
Acta Crystallogr.
2001,
E57:
252
25 Klügge J.
Ph.D. Thesis
Technische Universität München;
München:
2004.
26 Lemarchand A.
Bach T.
Synthesis
2005,
1977
