SCOPUS 정보 검색 플랫폼

Volumn , Issue 16, 2008, Pages 2479-2482

A stable synthetic equivalent of 2,3-dihydropyridine

Author keywords

Dihydropyridine; Enamine; Enone; Imine; Synthetic equivalent

Indexed keywords

2,3 DIHYDROPYRIDINE; DIHYDROPYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; DEPROTECTION REACTION; SYNTHESIS;

EID: 54149086304 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2008-1078056 Document Type: Article

Times cited : (7)

References (22)

1
- 0026529328
- (a) Baldwin, J. E.; Whitehead, R. C. Tetrahedron Lett. 1992, 33, 2059.
- (1992) Tetrahedron Lett , vol.33 , pp. 2059
- Baldwin, J.E.¹ Whitehead, R.C.²

2
- 0000571695
- (b) Yu, L.-B.; Chen, D.; Li, J.; Ramirez, J.; Wang, P. G.; Bott, S. G. J. Org. Chem. 1997, 62, 208.
- (1997) J. Org. Chem , vol.62 , pp. 208
- Yu, L.-B.¹ Chen, D.² Li, J.³ Ramirez, J.⁴ Wang, P.G.⁵ Bott, S.G.⁶

3
- 0032560715
- (c) Baldwin, J. E.; Spring, D. R.; Whitehead, R. C. Tetrahedron Lett. 1998, 39, 5417.
- (1998) Tetrahedron Lett , vol.39 , pp. 5417
- Baldwin, J.E.¹ Spring, D.R.² Whitehead, R.C.³

4
- 0001081918
- (d) Ruggeri, R. B.; Hansen, M. M.; Heathcock, C. H. J. Am. Chem. Soc. 1988, 110, 8734.
- (1988) J. Am. Chem. Soc , vol.110 , pp. 8734
- Ruggeri, R.B.¹ Hansen, M.M.² Heathcock, C.H.³

5
- 0032547244
- (e) Kaiser, A.; Billot, X.; Gateau-Olesker, A.; Marazano, C.; Das, B. C. J. Am. Chem. Soc. 1998, 120, 8026.
- (1998) J. Am. Chem. Soc , vol.120 , pp. 8026
- Kaiser, A.¹ Billot, X.² Gateau-Olesker, A.³ Marazano, C.⁴ Das, B.C.⁵

6
- 0032725566
- (f) Baldwin, J. E.; Claridge, T. D. W.; Culshaw, A. J.; Heupel, F. A.; Lee, V.; Spring, D. R.; Whitehead, R. C. Chem. Eur. J. 1999, 5, 3154.
- (1999) Chem. Eur. J , vol.5 , pp. 3154
- Baldwin, J.E.¹ Claridge, T.D.W.² Culshaw, A.J.³ Heupel, F.A.⁴ Lee, V.⁵ Spring, D.R.⁶ Whitehead, R.C.⁷

7
- 0033214301
- (g) Jakubowicz, K.; Abdeljelil, K. B.; Herdemann, M.; Martin, M.-T.; Gateau-Olesker, A.; Al-Mourabit, A.; Marazano, C.; Das, B. C. J. Org. Chem. 1999, 64, 7381.
- (1999) J. Org. Chem , vol.64 , pp. 7381
- Jakubowicz, K.¹ Abdeljelil, K.B.² Herdemann, M.³ Martin, M.-T.⁴ Gateau-Olesker, A.⁵ Al-Mourabit, A.⁶ Marazano, C.⁷ Das, B.C.⁸

8
- 0035854323
- (h) Gomez, J.-M.; Gil, L.; Ferroud, C.; Gateau-Olesker, A.; Martin, M.-T.; Marazano, C. J. Org. Chem. 2001, 66, 4898.
- (2001) J. Org. Chem , vol.66 , pp. 4898
- Gomez, J.-M.¹ Gil, L.² Ferroud, C.³ Gateau-Olesker, A.⁴ Martin, M.-T.⁵ Marazano, C.⁶

9
- 0037155507
- (i) Herdemann, M.; Al-Mourabit, A.; Martin, M.-T.; Marazano, C. J. Org. Chem. 2002, 67, 1890.
- (2002) J. Org. Chem , vol.67 , pp. 1890
- Herdemann, M.¹ Al-Mourabit, A.² Martin, M.-T.³ Marazano, C.⁴

10
- 49149121119
- (j) Wypych, J.-C.; Nguyen, T. M.; Nuhant, P.; Bénéchie, M.; Marazano, C. Angew. Chem. Int. Ed. 2008, 47, 5418.
- (2008) Angew. Chem. Int. Ed , vol.47 , pp. 5418
- Wypych, J.-C.¹ Nguyen, T.M.² Nuhant, P.³ Bénéchie, M.⁴ Marazano, C.⁵

11
- 84944053662
- Katritzky, A, Rees, C. W, Scriven, E. F. V, Eds, Pergamon: Oxford
- Jones, G. In Comprehensive Heterocyclic Chemistry II, Vol. 5; Katritzky, A.; Rees, C. W.; Scriven, E. F. V., Eds.; Pergamon: Oxford, 1996, 167.
- (1996) Comprehensive Heterocyclic Chemistry II , vol.5 , pp. 167
- Jones, G.¹

12
- 0001154977
- (a) Hasan, I.; Fowler, F. W. J. Am. Chem. Soc. 1978, 100, 6696.
- (1978) J. Am. Chem. Soc , vol.100 , pp. 6696
- Hasan, I.¹ Fowler, F.W.²

13
- 0011932732
- (b) Lasne, M.; Ripoll, J.; Guillemin, J.; Denis, J. Tetrahedron Lett. 1984, 35, 3847.
- (1984) Tetrahedron Lett , vol.35 , pp. 3847
- Lasne, M.¹ Ripoll, J.² Guillemin, J.³ Denis, J.⁴

14
- 1842830201
- (a) Kita, M.; Kondo, M.; Koyama, T.; Yamada, K.; Matsumoto, T.; Lee, K.; Woo, J.; Uemura, D. J. Am. Chem. Soc. 2004, 126, 4794.
- (2004) J. Am. Chem. Soc , vol.126 , pp. 4794
- Kita, M.¹ Kondo, M.² Koyama, T.³ Yamada, K.⁴ Matsumoto, T.⁵ Lee, K.⁶ Woo, J.⁷ Uemura, D.⁸

15
- 22844452334
- (b) Kita, M.; Ohishi, N.; Washida, K.; Kondo, M.; Koyama, T.; Yamada, K.; Uemura, D. Bioorg. Med. Chem. 2005, 13, 5253.
- (2005) Bioorg. Med. Chem , vol.13 , pp. 5253
- Kita, M.¹ Ohishi, N.² Washida, K.³ Kondo, M.⁴ Koyama, T.⁵ Yamada, K.⁶ Uemura, D.⁷

16
- 33846027848
- (c) Zou, Y.; Che, Q.; Snider, B. B. Org. Lett. 2006, 24, 5605.
- (2006) Org. Lett , vol.24 , pp. 5605
- Zou, Y.¹ Che, Q.² Snider, B.B.³

17
- 34250852306
- (d) Kim, J.; Thomson, R. J. Angew. Chem. Int. Ed. 2007, 46, 3104.
- (2007) Angew. Chem. Int. Ed , vol.46 , pp. 3104
- Kim, J.¹ Thomson, R.J.²

18
- 21644490169
- Kita, M.; Uemura, D. Chem. Lett. 2005, 454.
- (2005) Chem. Lett , pp. 454
- Kita, M.¹ Uemura, D.²

19
- 54149092882
- Born, S.; Olson, E. E.; Kobayashi, Y. Synthetic Studies towards (+)-Symbioimine, In Abstracts of Papers; 232nd National Meeting of the American Chemical Society: San Francisco CA, Sept 10-14, 2006, American Chemical Society: Washington D. C., 2006; ORGN-748.
- Born, S.; Olson, E. E.; Kobayashi, Y. Synthetic Studies towards (+)-Symbioimine, In Abstracts of Papers; 232nd National Meeting of the American Chemical Society: San Francisco CA, Sept 10-14, 2006, American Chemical Society: Washington D. C., 2006; ORGN-748.

20
- 54149094073
- 2, etc.), basic (NaOEt, NaOH, LDA, etc.), or nucleophilic conditions (dimedone, piperidine, NaSEt, etc.).
- 2, etc.), basic (NaOEt, NaOH, LDA, etc.), or nucleophilic conditions (dimedone, piperidine, NaSEt, etc.).

21
- 54149083344
- Experimental Procedure for Preparation of Compound 2 To a 50 mL round-bottom flask at 25°C was added 6 (1.23 g, 3.38 mmol) and benzene (34 mL, Pyridinium p-toluenesulfonate (PPTS, 85 mg, 0.34 mmol, 10 mol, was then added and the solution allowed stirring under reflux while monitoring by TLC. After 1 h, the reaction was quenched by the addition of sat. NaHCO3, and separated. The aqueous layer was extracted twice with EtOAc, the combined organics washed with brine, and dried over Na 2SO4. Concentration in vacuo yielded crude material which was then purified on SiO2 (hexane-EtOAc, 5:1) to yield compound 2 (1:1 mixture of diastereomers 2 and 2′, 1.07 g, 95, as a clear oil. 1H NMR (400 MHz, CDCl3, δ, 7.28-7.20 (m, 2 H and 2 H′, 7.18-7.08 (m, 3 H and 3 H′, 6.00-5.90 (m, 1 H and 1 H′, 5.32 (d, J, 17.2 Hz, 1 H and 1 H′, 5.23 d
- 2S: 345.1757; found: 345.1755.

22
- 54149092694
- Experimental Procedure for Preparation of Compound 1 To a 10 mL round-bottom flask at 25°C was added 2 (70 mg, 0.20 mmol) in THF (0.4 mL, and placed under a blanket of nitrogen. Then, Pd2dba 3·CHCl3 (5.2 mg, 0.005 mmol, 5 mol, and 1,4-bis(diphenylphosphino)butane (dppb, 8.6 mg, 0.020 mmol, 10 mol, were added and the solution allowed stirring while monitoring by TLC. Upon completion after 2 h, the solution was diluted with THF, filtered over Celite, and concentrated in vacuo to yield compound 1 as a viscous oil. 1H NMR (400 MHz, CDCl3, δ, 7.28-7.23 (m, 2 H, 7.20-7.14 (m, 3 H, 6.21 (dd, J, 3.5, 9.5 Hz, 1 H, 5.86 (dd, J, 2.5, 10.0 Hz, 1 H, 3.66 (dd, J, 7.0, 15.5 Hz, 1 H, 3.16 (dd, J, 12.0, 16.0 Hz, 1 H, 2.86 (t, J, 7.5 Hz, 2 H, 2.56 (t, J, 8.5 Hz, 2 H, 2.27 (m, 1 H, 0.98 (d, J, 7.5 Hz, 3 H, 13C NMR 100 MHz, CDCl
- 19N: 199.1356; found: 199.1357.

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.