A Mild and Efficient Synthesis of 2-Oxazolines via Transamidation–Cyclodehydrosulfurisation­ of Thioamides with 2-Aminoethanol

D. Raghavender Goud; Uma Pathak

doi:10.1055/s-0032-1317341

Synthesis, Table of Contents

Synthesis 2012; 44(23): 3678-3682
DOI: 10.1055/s-0032-1317341

paper

A Mild and Efficient Synthesis of 2-Oxazolines via Transamidation–Cyclodehydrosulfurisation of Thioamides with 2-Aminoethanol

D. Raghavender Goud

Synthetic Chemistry Division, Defence R & D Establishment, Jhansi Road, Gwalior 474002 (M.P.), India Fax: +91(751)2341148 Email: sc_drde@rediffmail.com

,

Uma Pathak*

Synthetic Chemistry Division, Defence R & D Establishment, Jhansi Road, Gwalior 474002 (M.P.), India Fax: +91(751)2341148 Email: sc_drde@rediffmail.com

› Author Affiliations

Abstract

All articles of this category

Abstract

Transamidation of thioamides with 2-aminoethanol, followed by cyclodehydrosulfurisation of the resultant N-(β-hydroxyethyl)thioamides, has been utilised for the mild and efficient synthesis of 2-oxazolines. The developed protocol was found to be of general applicability.

Key words

2-oxazolines - thioamides - 2-aminoethanol - transamidation - cyclodehydrosulfurisation

Full Text

References

References

1a Wiley RH, Bennett LL. Chem. Rev. 1949; 44: 447
1b Wong GS. K, Wu W. Oxazoles: Synthesis, Reactions, and Spectroscopy . In The Chemistry of Heterocyclic Compounds . Part B, Palmer DC. John Wiley & Sons; New Jersey: 2004: 331

2 Peterson T, Falk KE, Leong SA, Klein MP, Neilands JB. J. Am. Chem. Soc. 1980; 102: 7715
3 Genet JP, Thorimbert S, Touzin AM. Tetrahedron Lett. 1993; 34: 1159
4 Hamada Y, Kato S, Shioiri T. Tetrahedron Lett. 1985; 26: 3223
5 Wipf P, Miller CP. J. Am. Chem. Soc. 1992; 114: 10975
6 Li Q, Woods KW, Claiborne A, Gwaltney SL, Barr KJ, Liu G, Gehrke L, Credo RB, Hui YH, Lee J, Warner RB, Kovar P, Nukkala MA, Zielinski NA, Tahir SK, Fitzgerald M, Kim KH, Marsh K, Frost D, Ng SC. Bioorg. Med. Chem. Lett. 2002; 12: 465
7 Campiani G, de Angelis M, Armaroli S, Fattorusso C, Catalanotti B, Ramunno A, Nacci V, Novellino E, Grewer C, Ionescu D, Rauen T, Griffiths R, Sinclair C, Fumagalli E, Mennini T. J. Med. Chem. 2001; 44: 2507
8 Meyers AI, Mihelich ED. Angew. Chem., Int. Ed. Engl. 1976; 15: 270
9 Reuman M, Meyers AI. Tetrahedron 1985; 41: 837
10 Meyers AI, Temple DL, Haidukewych D, Mihelich ED. J. Org. Chem. 1974; 39: 2787
11 Meyers AI. Acc. Chem. Res. 1978; 11: 375
12 Gant TG, Meyers AI. Tetrahedron 1994; 50: 2297
13 Bandgar BP, Pandit SS. Tetrahedron Lett. 2003; 44: 2331
14 Wenker H. J. Am. Chem. Soc. 1935; 57: 9
15 Frump JA. Chem. Rev. 1971; 71: 483
16 Vorbrüggen H, Krolikiewicz K. Tetrahedron 1993; 49: 9353
17 Cwik A, Hell Z, Hegedüs A, Finta Z, Horváth Z. Tetrahedron Lett. 2002; 43: 3985
18 Marrero-Terrero AL, Loupy A. Synlett 1996; 245
19 Meyers AI, Slade J. J. Org. Chem. 1980; 45: 2785
20 Kamata K, Agata I, Meyers AI. J. Org. Chem. 1998; 63: 3113
21 Oussaid B, Berlan J, Soufiaoui M, Garrigues B. Synth. Commun. 1995; 25: 659
22 Badiang JG, Aube J. J. Org. Chem. 1996; 61: 2484
23 Ishihara M, Togo H. Tetrahedron 2007; 63: 1474
24 Bolm C, Weickhardt K, Zehnder M, Ranff T. Chem. Ber. 1991; 124: 1173
25 Clarke DS, Wood R. Synth. Commun. 1996; 26: 1335
26 Jnaneshwara GK, Deshpande VH, Lalithambika M, Ravindranathan T, Bedekar AV. Tetrahedron Lett. 1998; 39: 459
27 Moghadam M, Mirkhani V, Tangestaninejad S, Mohammadpoor-Baltork I, Kargar H. J. Iran. Chem. Soc. 2009; 6: 251
28 Lafargue P, Guenot P, Lellouche JP. Synlett 1995; 171
29 Mahler SG, Serra GL, Antonow D, Manta E. Tetrahedron Lett. 2001; 42: 8143

30a Pandey LK, Pathak U, Mathur S, Suryanarayana MV. S. Synthesis 2012; 44: 377
30b Pathak U, Bhattacharyya S, Dhruwansh V, Pandey LK, Tank R, Suryanarayana MV. S. Green Chem. 2011; 13: 1648
30c Pandey LK, Pathak U, Mazumder A, Mathur S. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 2010; 49: 1225

31 Pathak U, Pandey LK, Tank R. J. Org. Chem. 2008; 73: 2890
32 Luisa F, Riccardo P, Giorgio G, Mario G, Alfonso V, Roberto M, Giovanni D. Des. Monomers Polym. 2008; 11: 243
33 Pridgen LN. J. Org. Chem. 1982; 47: 4319
34 Ilkgul B, Gunes D, Sirkecioglu O, Bicak N. Tetrahedron Lett. 2010; 51: 5313
35 Fomum ZT. J. Chem. Res., Synop. 1985; 69

Supplementary Material

Supporting Information

A Mild and Efficient Synthesis of 2-Oxazolines via Transamidation–Cyclodehydrosulfurisation­ of Thioamides with 2-Aminoethanol

A Mild and Efficient Synthesis of 2-Oxazolines via Transamidation–Cyclodehydrosulfurisation of Thioamides with 2-Aminoethanol