SCOPUS 정보 검색 플랫폼

Volumn 78, Issue 2, 2009, Pages 319-324

First formation of thiepino[2,3-b]- and thiepino[3,2-a]-indolizine derivatives

Author keywords

Allyl Anion; Cyclization; Synthesis; Thiepino 2,3 a indolizine; Thiepino 2,3 b indolizine

Indexed keywords

EID: 62649086161 PISSN: 03855414 EISSN: None Source Type: Journal
DOI: 10.3987/COM-08-11536 Document Type: Article

Times cited : (4)

References (24)

1
- 62649112957
- Preparation of new nitrogen-bridged heterocycles. 65
- Preparation of new nitrogen-bridged heterocycles. 65

2
- 62649131654
- For part 64 of this series, see
- For part 64 of this series, see. Kakehi A., Suga H., and Sato S. Heterocycles 77 (2009) 471
- (2009) Heterocycles , vol.77 , pp. 471
- Kakehi, A.¹ Suga, H.² Sato, S.³

3
- 0024992083
- Kakehi A., Ito S., Yamada N., and Yamaguchi K. Chem. Pharm. Bull. 38 (1990) 1527
- (1990) Chem. Pharm. Bull. , vol.38 , pp. 1527
- Kakehi, A.¹ Ito, S.² Yamada, N.³ Yamaguchi, K.⁴

4
- 0026746520
- Kakehi A., Ito S., Fujii T., Ueda T., and Hirata T. Chem. Pharm. Bull. 40 (1992) 2313
- (1992) Chem. Pharm. Bull. , vol.40 , pp. 2313
- Kakehi, A.¹ Ito, S.² Fujii, T.³ Ueda, T.⁴ Hirata, T.⁵

5
- 0033958677
- Kakehi A., Ito S., Suga H., Takahashi H., and Dobashi K. Heterocycles 52 (2000) 215
- (2000) Heterocycles , vol.52 , pp. 215
- Kakehi, A.¹ Ito, S.² Suga, H.³ Takahashi, H.⁴ Dobashi, K.⁵

6
- 0030825651
- Marx K., and Eberbach W. Tetrahedron 53 (1997) 14687
- (1997) Tetrahedron , vol.53 , pp. 14687
- Marx, K.¹ Eberbach, W.²

7
- 62649159975
- 2CH=CH), 6.93 (1H, dt, J=7.1, 7.1, and 1.2 Hz, 6-H), 7.27 (1H, ddd, J=9.2, 6.8, and 1.1 Hz, 7-H), 8.26 (1H, dt, J=9.3, 1.1, and 1.1 Hz, 8-H), and 9.42 (1H, dt, J=7.1, 1.1, and 1.1 Hz, 5-H).
- 2CH=CH), 6.93 (1H, dt, J=7.1, 7.1, and 1.2 Hz, 6-H), 7.27 (1H, ddd, J=9.2, 6.8, and 1.1 Hz, 7-H), 8.26 (1H, dt, J=9.3, 1.1, and 1.1 Hz, 8-H), and 9.42 (1H, dt, J=7.1, 1.1, and 1.1 Hz, 5-H).

8
- 62649118262
- 2CH=CH), 8.06 (1H, quint, J=1.0 Hz, 8-H), and 9.32 (1H, d, J=7.2 Hz, 5-H).
- 2CH=CH), 8.06 (1H, quint, J=1.0 Hz, 8-H), and 9.32 (1H, d, J=7.2 Hz, 5-H).

12
- 62649153848
- 5c,1H NMR (CDCl3) δ: 1.25, 1.39, and 1.41 (each 3H, t, J=7.1 or 7.2 Hz, 3xCO2CH2CH3, 3.08 (2H, dd, J=7.1 and 1.5 Hz, CH2CO2Et, 4.13 and 4.35 (each 2H, q, J=7.2 Hz, 2xCO2CH2CH3, 5.82 (1H, dt, J=15.3, 7.1, and 7.1 Hz, SCH=CHCH2, and 6.21 (1H, dt, J=15.4, 1.2, and 1.2 Hz, SCH=CH).10
- 10

15
- 62649133808
- 6c,1H NMR (CDCl3) δ: 1.29, 1.37, and l.40 (each 3H, t, J=7.0 or 7.1 Hz, 3xCO2CH2CH3, 3.32 (2H, dd, J=6.9 and 1.7 Hz, CH2CO2Et, 4.18 and 4.34 (each 2H, q, J=7.2 Hz, 2xCO2CH2CH3, 5.82 (1H, dt, J=9.4, 6.8, and 6.8 Hz, SCH=CHCH2, and 6.26 (1H, dt, J=9.5, 1.6, and 1.6 Hz, SCH=CH).10
- 10

16
- 62649166894
- The separation of these indolizine mixtures 4a+5a+6a, 4b+5b+6b, and 4c+5c+6c were unsuccessful, but they gave satisfactory elemental analyses
- The separation of these indolizine mixtures 4a+5a+6a, 4b+5b+6b, and 4c+5c+6c were unsuccessful, but they gave satisfactory elemental analyses.

17
- 62649111119
- 6S: C, 59.25; H, 5.72; N, 3.45. Found: C, 59.41; H, 5.66; N, 3.35.
- 6S: C, 59.25; H, 5.72; N, 3.45. Found: C, 59.41; H, 5.66; N, 3.35.

18
- 62649147377
- 6S: C, 60.13; H, 6.01; N, 3.34. Found: C, 60.28; H, 5.98; N, 3.22.
- 6S: C, 60.13; H, 6.01; N, 3.34. Found: C, 60.28; H, 5.98; N, 3.22.

19
- 62649160476
- 6S: C, 60.95; H, 6.28; N, 3.23. Found: C, 60.95; H, 6.35; N, 3.16.
- 6S: C, 60.95; H, 6.28; N, 3.23. Found: C, 60.95; H, 6.35; N, 3.16.

20
- 62649162365
- 11a: mp 134-137°C, v (KBr) cm-1 1698 and 1747. 1H NMR (CDCl3) δ:1.31 and 1.44 (each 3H, t, J=7.1 or 7.2 Hz, 2xOCH2CH3, 3.43 (2H, d, J=7.3 Hz, 2-H, 4.22 and 4.40 (each 2H, q, J=7.1 or 7.2 Hz, 2xOCH2CH3, 7.04 (1H, dt, J=6.8, 1.2, and l.2 Hz, 8-H, 7.19 (1H, t, J=7.3 Hz, 3-H, 7.46 (1H, ddd, J=9.1, 7.0, and 1.2 Hz, 9-H, 8.23 (1H, dt, J=9.0, 1.2, and l.2 Hz, 10-H, 8.95 (1H, dt, J=6.7, 1.2, and 1.2 Hz, 7-H, 13C NMR (CDCl3) δ: 14.19, 14.55, 35.86, 60.42, 61.45, 100.90, 114.92, 119.24, 121.41, 127.24, 127.59, 128.96, 141.50, 143.79, 145.50, 162.99, 169.17, 171.78. HRMS m/z calcd for C18H18NO5S M++H, 360.0900, found: 360.0898
- ++H): 360.0900, found: 360.0898.

21
- 62649112051
- 11b: mp 121-124 °C, v (KBr) cm-1 1664, 1701, 1748. 1H NMR (CDCl3) δ: 1.30 and 1.43 (each 3H, t, J-7.1 or 7.2 Hz, 2xOCH2CH3, 2.48 (3H, s, 9-Me, 3.41 (2H, d, J=7.3 Hz, 2-H, 4.22 and 4.39 (each 2H, q, J=7.1 or 7.2 Hz, 2xOCH2CH3, 8.00 (1H, br s, 10-H, 8.79 (1H, d, J=6.8 Hz, 7-H, 13C NMR (CDCl3) δ: 14.19, 14.57, 21.93, 35.87, 60.32, 61.43, 99.94, 117.23, 118.21, 121.02, 126.63, 127.18, 141.19, 141.69, 144.26, 145.90, 163.15, 169.24, 171.32. HRMS m/z calcd for C19H20NO5S M++H, 374.1057, found: 374.1025
- ++H): 374.1057, found: 374.1025.

22
- 62649132842
- 12c, mp 117-120 °C, v (KBr) cm-1 1668, 1692, and 1736. 1H NMR (CDCl3) δ: 1.30 and 1.45 (each 3H, t, J=7.1 or 7.2 Hz, 2xOCH2CH3, 2.35 (3H, s, 8-Me, 2.89 (3H, s, 6-Me, 3.39 (2H, d, J=7.3 Hz, 2-H, 4.21 and 4.41 (each 2H, q, J=7.0 or 7.l Hz, 2xOCH2CH3, 7.03 (1H, br s, 9-H, 7.07 (1H, t, J=7.3 Hz, 3-H, 9.19 (1H, br s, 9-H, 13C NMR (CDCl3) δ: 14.20, 14.55, 18.32, 20.00, 36.17, 60.64, 61.34, 107.99, 113.60, 124.69, 125.57, 125.82, 129.55, 131.54, 135.47, 142.45, 144.73, 160.39, 169.47, 178.12. HRMS m/z calcd for C20H22NO5S M++H, 388.1232, found: 388.1191
- ++H): 388.1232, found: 388.1191.

23
- 62649093029
- Because thiepinoindolizines 11a,b and 12c were considerably unstable, their compositions were confirmed by high resolution mass spectra
- Because thiepinoindolizines 11a,b and 12c were considerably unstable, their compositions were confirmed by high resolution mass spectra.

24
- 62649134740
- Other proton signals were overlapped with those of major products 4a-c
- Other proton signals were overlapped with those of major products 4a-c.

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.