Abstract
Different arylnitriles react with β-aminoalcohols in the presence of catalytic amounts of Bi(III) salts such as Bi(TFA)3 , Bi(OTf)3 and BiOClO4 ·xH2 O producing the corresponding 2-aryloxazolines in high yields. Selective synthesis of mono- and bis-oxazolines from dicyanobenzenes and selective conversion of arylnitriles to their 2-oxazolines in the presence of alkylnitriles can be considered as noteworthy advantages of this method.
Key words
oxazolines - aminoalcohols - nitriles - bismuth(III) salts
References
1a Genet JP.
Thorimbert S.
Touzin AM.
Tetrahedron Lett.
1993,
34:
1159
1b Wipf P.
Venkatraman S.
Synlett
1997,
1
1c Li Q.
Woods KW.
Claiborne A.
Gwaltney SL.
Barr KJ.
Liu G.
Gehrke L.
Credo RB.
Hua Hui Y.
Lee J.
Warner RB.
Kovar P.
Nukkala MA.
Zielinski NA.
Tahir SK.
Fitzgerald M.
Kim KH.
Marsh K.
Frost D.
Ng S.-C.
Rosenberg S.
Sham HL.
Bioorg. Med. Chem. Lett.
2002,
12:
465
2a Gant TG.
Meyers AI.
Tetrahedron
1994,
50:
2297
2b Yang D.
Yip Y.-C.
Wang X.-C.
Tetrahedron Lett.
1997,
38:
7083
3 Greene TW.
Wutz PGM. In Protecting Groups in Organic Synthesis
2nd ed.:
John Wiley and Sons;
New York:
1991.
4a Jiang Y.
Jiang Q.
Zhu G.
Zhang X.
Tetrahedron Lett.
1997,
38:
215
4b McManus HA.
Barry SM.
Andersson PG.
Guiry PJ.
Tetrahedron
2004,
60:
3405
4c Lee A.
Kim W.
Lee J.
Hyeon T.
Kim BM.
Tetrahedron: Asymmetry
2004,
15:
2595
5a Vorbrüggen H.
Krolikiewicz K.
Tetrahedron Lett.
1993,
34:
9353
5b Cwik A.
Hell Z.
Hegedüs A.
Z.
Horvath Z.
Tetrahedron Lett.
2002,
43:
3985
5c Bandgar BP.
Pandit SS.
. Tetrahedron Lett.
2003,
44:
2331
6a Miller D.
Umbricht G.
Weber B.
Pfaltz A.
Helv. Chim. Acta
1991,
74:
232
6b Zhou P.
Blubaum JE.
Burns CT.
Natale NR.
Tetrahedron Lett.
1997,
38:
7019
7a Clarke DS.
Wood R.
Synth. Commun.
1996,
26:
1335
7b Jnaneshwara GK.
Deshpande VH.
Lalithambika M.
Ravindranathan T.
Bedekar AV.
Tetrahedron Lett.
1998,
39:
459
8a Corey EJ.
Ishihara K.
Tetrahedron Lett.
1992,
33:
6807
8b Lafargue P.
Guenot P.
Lellouche JP.
Heterocycles
1995,
41:
947
9 Badiang JG.
Aube J.
J. Org. Chem.
1996,
61:
2484
10 Minakata S.
Nishimura M.
Takahashi T.
Oderaotoshi Y.
Komatsu M.
Tetrahedron Lett.
2001,
42:
9019
11a Reglinski J. In Chemistry of Arsenic, Antimony and Bismuth
Norman NC.
Blackie Academic and Professional;
New York:
1998.
p.403-440
11b Suzuki H.
Ikegami T.
Matano Y.
Synthesis
1997,
249
11c Leonard NM.
Wieland LC.
Mohan RS.
Tetrahedron
2002,
58:
8373
11d Anderson AM.
Blazek JM.
Garg P.
Payne BJ.
Mohan RS.
Tetrahedron Lett.
2000,
41:
1527
11e Chakraborti AK.
Shivani GR.
Synlett
2003,
1805
11f Sabitha G.
Venkata Reddy E.
Swapna R.
Mallikarjun Reddy N.
Yadav JS.
Synlett
2004,
1276
11g Yadav JS.
Reddy BVS.
Premalatha K.
Synlett
2004,
963
11h Grouch RD.
Romany CA.
Kreshock AC.
Menconi KA.
Zile JL.
Tetrahedron Lett.
2004,
45:
1279
11i Ghosh R.
Maiti S.
Chakraborty A.
Synlett
2005,
115
11j Nattier BA.
Eash KJ.
Mohan RS.
Synthesis
2001,
1010
12a Mohammadpoor-Baltork I.
Aliyan H.
Synth. Commun.
1998,
28:
3943
12b Mohammadpoor-Baltork I.
Aliyan H.
Synth. Commun.
1999,
29:
2741
12c Mohammadpoor-Baltork I.
Tangestaninejad S.
Aliyan H.
Mirkhani V.
Synth. Commun.
2000,
30:
2365
12d Mohammadpoor-Baltork I.
Aliyan H.
Khosropour AR.
Tetrahedron
2001,
57:
5851
12e Mohammadpoor-Baltork I.
Khosropour AR.
Aliyan H.
J. Chem. Res., Synop.
2001,
280
12f Mohammadpoor-Baltork I.
Khosropour AR.
Aliyan H.
Synth. Commun.
2001,
31:
3411
12g Mohammadpoor-Baltork I.
Khosropour AR.
Molecules
2001,
996
12h Firouzabadi H.
Mohammadpoor-Baltork I.
Kolagar S.
Synth. Commun.
2001,
31:
905
12i Mohammadpoor-Baltork I.
Kharamesh B.
Kolagar S.
Synth. Commun.
2002,
32:
1633
12j Mohammadpoor-Baltork I.
Khosropour AR.
Monatsh. Chem.
2002,
133:
189
12k Mohammadpoor-Baltork I.
Khodaei MM.
Nikoofar K.
Tetrahedron Lett.
2003,
44:
591
13a Khodaei MM.
Khosropour AR.
Hosseini Jomor JS.
J. Chem. Res., Synop.
2003,
638
13b Khosropour AR.
Khodaei MM.
Kookhazadeh M.
Tetrahedron Lett.
2004,
45:
1725
13c Khodaei MM.
Khosropour AR.
Ghozati K.
Tetrahedron Lett.
2004,
45:
3525
13d Khodaei MM.
Khosropour AR.
Jowkar M.
Synthesis
2005,
1301
13e Khodaei MM.
Khosropour AR.
Ghozati K.
J. Braz. Chem. Soc.
2005,
16:
673
14
General Procedure.
3 and 0.05-0.066 mmol of Bi(OTf)3 or BiOClO4 ·xH2 O]. The reaction mixture was stirred under reflux conditions for the appropriate time according to Table
[1 n -hexane-EtOAc, 2:1). The reaction mixture was cooled to r.t. and the crude product was purified by column chromatography on neutral alumina to afford the pure product (Table
[1 2l : mp 98-100 °C. IR (KBr): 3040, 2900, 1647, 1490, 1230, 1056, 930, 670 cm-1 . 1 H NMR (500 MHz, CDCl3 ): δ = 4.09 (t, J = 9.6 Hz, 2 H), 4.46 (t, J = 9.6 Hz, 2 H), 7.53 (t, J = 7.8 Hz, 1 H), 7.74 (d, J = 7.7 Hz, 1 H), 8.18 (d, J = 7.8 Hz, 1 H), 8.22 (s, 1 H). Anal. Calcd for C10 H8 N2 O: C, 69.76; H, 4.68; N, 16.27. Found: C, 69.80; H, 4.70; N, 16.15.
15 Bower JF.
Martin CJ.
Rawson DJ.
Slawin AMZ.
Williams JMJ.
J. Chem. Soc., Perkin Trans. 1
1995,
333
16a Witte H.
Seeliger W.
Liebigs Ann. Chem.
1974,
996
16b Poindexter GS.
J. Heterocycl. Chem.
1983,
20:
1431
16c Pridgen LN.
J. Org. Chem.
1982,
47:
4319
16d Pirrung MC.
Tumey LN.
J. Comb. Chem.
2000,
2:
675
16e George B.
J. Org. Chem.
1977,
42:
441
16f Bandgar BP.
Pandit SS.
Tetrahedron Lett.
2003,
44:
2331
16g Schöning A.
Debaerdemaeker T.
Zander M.
Friedrichsen W.
Chem. Ber.
1989,
122:
1119
16h Kumagai T.
Kawamura Y.
Mukai T.
Tetrahedron Lett.
1983,
24:
2279
16i Chen L.
J. Mater. Sci. Lett.
2003,
22:
953
