Efficient synthesis of highly substituted thiophenes
1259
CH) ppm; 13C NMR: ꢂ ¼ 13.9 (Me), 45.4 (NMe2), 51.8 (OMe),
62.3 (OCH2), 115.9 (C), 132.8 (CH), 136.3 (C), 155.0 (C),
163.2 (C¼O), 167.1 (C¼O), 179.1 (C¼O) ppm.
References
1. Gronowitz S (ed) (1991) The Chemistry of Heterocyclic
Compounds: Thiophene and Its Derivatives, vol 44.
Wiley, New York
2. Bertram HJ, Emberger R, Gu¨ntert M, Sommer H,
Werkhoff P (1993) In: Hopp R, Mori K (eds) Recent
Developments in Flavor and Fragrance Chemistry. VCH,
Weinheim
3. Sperry JB, Wright DL (2005) Curr Opin Drug Discovery
Dev 8:723
4. Siebert C (2004) Chem Unserer Zeit 38:320
5. Roncali J (1992) Chem Rev 92:711
Ethyl 2-(dimethylamino)-3-(2-ethoxy-2-oxoacetyl)thiophene-
3-carboxylate (4d, C13H17NO5S)
Yellow oil; yield: 0.45g (75%); IR (KBr): ꢃꢀ¼ 1693, 1633,
1605, 1556, 1509, 1399, 1307, 1260 cmꢀ1; EI-MS: m=z
(%) ¼ 299 (Mþ, 10), 255 (64), 254 (45), 226 (66), 73 (62),
45 (100); 1H NMR: ꢂ ¼ 1.31 (t, 3J ¼ 7.2 Hz, Me), 1.41 (t, 3J ¼
7.2 Hz, Me), 3.06 (s, NMe2), 4.22 (q, 3J ¼ 7.2Hz, OCH2), 4.29
(q, 3J ¼ 7.2 Hz, OCH2), 7.31 (s, CH) ppm; 13C NMR: ꢂ ¼ 14.1
(Me), 14.2 (Me), 45.2 (NMe2), 60.7 (OCH2), 61.8 (OCH2),
116.4 (C), 133.0 (CH), 137.5 (C), 160.3 (C), 160.5 (C¼O),
164.5 (C¼O), 178.2 (C¼O) ppm.
6. Skotheim TA (ed) (1986) Handbook of Conductive
Polymers. Marcel Dekker, New York
7. Nalwa HS (1993) Adv Mater 5:341
8. Tarasova OA, Klyba LV, Vvedensky VY, Nedolya NA,
Trofimov BA, Brandsma L, Verkruijsse HD (1998) Eur J
Org Chem:253
Ethyl 2-(dimethylamino)-3-(2-ethoxy-2-oxoacetyl)-5-phenyl-
thiophene-4-carboxylate (4e, C19H21NO5S)
Yellow oil; yield: 0.45 g (75%); IR (KBr): ꢃꢀ¼ 1700, 1692,
1634, 1609, 1502, 1310, 1268, 1153, 1076cmꢀ1; EI-MS:
m=z (%) ¼ 375 (Mþ, 10), 330 (75), 302 (60), 298 (44), 77
9. Ong CW, Chen CM, Wang LF (1998) Tetrahedron Lett
39:9191
10. Stephensen H, Zaragoza F (1997) J Org Chem 62:6096
11. Marson CM, Campbell J (1997) Tetrahedron Lett 38:7785
12. Yavari I, Hosseini N, Moradi L (2008) Monatsh Chem
139:133
13. Yavari I, Zare H (2007) Monatsh Chem 138:787
14. Yavari I, Hossaini Z, Sabbaghan M, Ghazanfarpour-
Darjani M (2007) Monatsh Chem 138:677
15. Habibi H, Mousavifar L, Yavari I, Yazdanbakhsh MR
(2007) Monatsh Chem 138:603
1
3
(85), 73 (80), 45 (100); H NMR: ꢂ ¼ 1.23 (t, J ¼ 7.2 Hz,
Me), 1.36 (t, 3J ¼ 7.2 Hz, Me), 3.12 (s, NMe2), 4.10 (q,
3J ¼ 7.2 Hz, OCH2), 4.26 (q, 3J ¼ 7.2 Hz, OCH2), 6.85
(t, 3J ¼ 8.2 Hz, 2CH), 7.42 (t, 3J ¼ 8.2 Hz, CH), 8.15 (d,
3J ¼ 8.2 Hz, 2CH) ppm; 13C NMR: ꢂ ¼ 13.8 (Me), 14.2
(Me), 44.5 (NMe2), 61.2 (OCH2), 62.0 (OCH2), 114.2 (C),
127.3 (C), 128.5 (2CH), 129.4 (CH), 130.5 (2CH), 131.7
(C), 137.8 (C), 156.3 (C), 160.1 (C¼O), 165.2 (C¼O), 178.2
(C¼O) ppm.
16. Yavari I, Sabbaghan M, Hossaini Z (2006) Synlett:2501