The application of vinamidinium salts to the synthesis of 2,4-disubstituted thiophenes

Tetrahedron Letters

Volumn 46, Issue 8, 2005, Pages 1319-1320

  Clemens, Ryan T ^a   Smith, Stanton Q ^a  

^a VIRGINIA MILITARY INSTITUTE   (United States)

Author keywords

Methyl thioglycolate; Thiophenes; Vinamidinium salts

Indexed keywords

AMIDINE; CARBOXYLIC ACID DERIVATIVE; THIOGLYCOLIC ACID DERIVATIVE; THIOPHENE DERIVATIVE;

ARTICLE; CHEMICAL PROCEDURES; CHEMICAL REACTION; POLYMERIZATION; SYNTHESIS;

EID: 13244258444     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.12.113     Document Type: Article

References (11)

1. D. Lloyd, and H. McNabb Angew. Chem., Int. Ed. Engl. 15 1976 459 468
2. J.T. Gupton, D.A. Krolikowski, R.H. Yu, S.W. Riesinger, and J.A. Sikorski J. Org. Chem. 55 1990 4735 4740
3. J Roncali Chem. Rev. 92 1992 711 738
4. G. Kirsch, and D. Prim Synth. Commun. 24 1994 1721 1726
5. S. Hauptmann, and E.M. Werner J. Prakt. Chem. 314 1972 499 506
6. J. Liebscher, and H. Hartmann J. Prakt. Chem. 318 1976 731 744
7. P.T. Gallagher, J.L. Palmer, and S.E. Morgan J. Chem. Soc., Perkin Trans. 1 1990 3212 3214
8. General procedure: All reagents and solvents were obtained from Aldrich and ACROS and used without further purification. To a flame dried one-neck round-bottom flask equipped with magnetic stirring, reflux condenser, and nitrogen atmosphere was added the vinamidinium salt (0.300 g). Anhydrous DMF (2-3 mL) was added via syringe. Methyl thioglycolate (1.1-1.4 equiv) was added via microliter syringe. CAUTION: Handle methyl thioglycolate only in a good fume hood. The mixture was allowed to reflux overnight (15-18 h) under a nitrogen atmosphere. The flask was cooled to room temperature and the mixture was partitioned between ethyl acetate and saturated ammonium chloride (2×). The combined aqueous layers were extracted with fresh ethyl acetate, the combined ethyl acetate layers were then dried over sodium sulfate. The drying agent was filtered and the solvents removed in vacuo to give the crude material
9. R. Leardini, G. Martelli, P. Spagnalo, and M. Tiecco J. Chem. Soc. (C) 1970 1464 1469
10. Dublanchet, A.-C.; Compere, D.; Cluzeau, P.; Blais, S. U.S. Patent 2004072871, 2004; Chem. Abstr. 140:217508 CA
11. 2S, 232.0558, obsd 232.0555