Synthesis of 4-Isobutyl Substituted Thiophenes by Gewald Reaction

Monatshefte fur Chemie

Volumn 127, Issue 3, 1996, Pages 297-303

  Gutschow M ^a   Schroter H ^a   Kuhnle, G ^a   Eger, K ^a  

^a UNIVERSITY OF LEIPZIG   (Germany)

Author keywords

2 aminothiophenes; Gewald reaction; Methylketones

Indexed keywords

EID: 1542737981     PISSN: 00269247     EISSN: None     Source Type: Journal    
DOI: 10.1007/BF00813795     Document Type: Article

References (12)

1. Gewald K, Schinke E, Böttcher H (1966) Chem Ber 99: 94
2. For recent reviews, see: [a] Rudorf W-D, Methoden Org Chemie, 4th edn. (Houben-Weyl) 1994, vol. E 6a, pp 186-555; [b] Sabnis RW (1994) Sulfur Reports 16: 1
3. For recent reviews, see: [a] Rudorf W-D, Methoden Org Chemie, 4th edn. (Houben-Weyl) 1994, vol. E 6a, pp 186-555; [b] Sabnis RW (1994) Sulfur Reports 16: 1
4. Gewald K, Schinke E (1966) Chem Ber 99: 2712
5. Dickore K, Luerssen K (Bayer AG), EP 4931, 1979; CA (1980) 92: P110837k
6. Dickore K, Luerssen K (Bayer AG), EP 4931, 1979; CA (1980) 92: P110837k
7. Peet NP, Sunder S, Barbuch RJ, Vinogradoff AP, (1986) J Heteocycl Chem 12: 129
8. 2), 103.0 (C-3), 105.1 (C-5), 126.4 (C-4′), 127.1 (C-2′), 128.6 (C-3′), 138.2 and 140.5 (C-4 and C-1′), 164.7 (C-2), 165.1 (C-O) ppm
9. 13C NMR values were in accordance with Ref. [8]
10. Gewald K, Hain U, Gruner M (1988) Chem Ber 121: 573
11. Julia S, Torrent J, Olle J, Ramio J, Sanz M (1974) Affinidad 31: 117
12. When performing the Gewald reaction with 4-methyl-2-pentanone and ethyl cyanoacetate under argon or, otherwise, under a weak air stream, the formation of 5b was not remarkably affected. This may indicate that sulfur has acted as oxidizing agent.