SCOPUS 정보 검색 플랫폼

Synlett

Volumn , Issue 2, 2007, Pages 227-230

New indolizine template from the Ugi reaction

(3) El Kaim, Laurent a Gizolme, Marie a Grimaud, Laurence a

a Ecole Nationale Superieure de Techniques Avancees (France)

Author keywords

Indolizine; Isocyanide; Multicomponent reaction; Sonogashira coupling; Ugi reaction

Indexed keywords

AMINE; CHLOROACETIC ACID; INDOLIZINE DERIVATIVE; PROPARGYLAMINE; PYRIDINIUM DERIVATIVE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CHEMICAL REACTION; CYCLOADDITION; OXIDATION; SONOGASHIRA REACTION;

EID: 33847013752 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2007-968011 Document Type: Article

Times cited : (41)

References (58)

1
- 26844537872
- For recent reviews, see: a
- For recent reviews, see: (a) Banfi, L.; Riva, R. Org. React. 2005, 65, 1.
- (2005) Org. React , vol.65 , pp. 1
- Banfi, L.¹ Riva, R.²

2
- 0037391570
- (b) Zhu, J. Eur. J. Org. Chem. 2003, 1133.
- (2003) Eur. J. Org. Chem , pp. 1133
- Zhu, J.¹

3
- 1642338545
- (c) Ugi, I.; Werner, B.; Dömling, A. Molecules 2003, 8, 53.
- (2003) Molecules , vol.8 , pp. 53
- Ugi, I.¹ Werner, B.² Dömling, A.³

4
- 0037238724
- (d) Hulme, C.; Gore, V. Curr. Med. Chem. 2003, 10, 51.
- (2003) Curr. Med. Chem , vol.10 , pp. 51
- Hulme, C.¹ Gore, V.²

5
- 0034665244
- (e) Bienaymé, H.; Hulme, C.; Oddon, G.; Schmitt, P. Chem. Eur. J. 2000, 6, 3321.
- (2000) Chem. Eur. J , vol.6 , pp. 3321
- Bienaymé, H.¹ Hulme, C.² Oddon, G.³ Schmitt, P.⁴

6
- 0001134412
- (f) Dömling, A.; Ugi, I. Angew. Chem. Int. Ed. 2000, 39, 3168.
- (2000) Angew. Chem. Int. Ed , vol.39 , pp. 3168
- Dömling, A.¹ Ugi, I.²

7
- 31544434530
- (g) Dömling, A. Chem. Rev. 2006, 106, 17.
- (2006) Chem. Rev , vol.106 , pp. 17
- Dömling, A.¹

8
- 28244470363
- (a) Lu, K.; Luo, T.; Xiang, Z.; You, Z.; Fathi, R.; Chen, J.; Yang, Z. J. Comb. Chem. 2005, 7, 958.
- (2005) J. Comb. Chem , vol.7 , pp. 958
- Lu, K.¹ Luo, T.² Xiang, Z.³ You, Z.⁴ Fathi, R.⁵ Chen, J.⁶ Yang, Z.⁷

9
- 1242285045
- (b) Paulvannan, K. J. Org. Chem. 2004, 69, 1207.
- (2004) J. Org. Chem , vol.69 , pp. 1207
- Paulvannan, K.¹

10
- 0033525092
- (c) Zhang, J.; Jacobson, A.; Rusche, J. R.; Herlihy, W. J. Org. Chem. 1999, 64, 1074.
- (1999) J. Org. Chem , vol.64 , pp. 1074
- Zhang, J.¹ Jacobson, A.² Rusche, J.R.³ Herlihy, W.⁴

11
- 1842637394
- (d) Akritopoulou-Zanze, I.; Gracias, V.; Moore, J. D.; Djuric, S. W. Tetrahedron Lett. 2004, 45, 3421.
- (2004) Tetrahedron Lett , vol.45 , pp. 3421
- Akritopoulou-Zanze, I.¹ Gracias, V.² Moore, J.D.³ Djuric, S.W.⁴

12
- 2242457652
- (e) Janvier, P.; Bienaymé, H.; Zhu, J. Angew. Chem. Int. Ed. 2002, 41, 4291.
- (2002) Angew. Chem. Int. Ed , vol.41 , pp. 4291
- Janvier, P.¹ Bienaymé, H.² Zhu, J.³

13
- 0037016980
- (f) Wright, D. L.; Robotham, C. V.; Aboud, K. Tetrahedron Lett. 2002, 43, 943.
- (2002) Tetrahedron Lett , vol.43 , pp. 943
- Wright, D.L.¹ Robotham, C.V.² Aboud, K.³

14
- 0347627364
- (a) Gracias, V.; Moore, J. D.; Djuric, S. W. Tetrahedron Lett. 2004, 45, 417.
- (2004) Tetrahedron Lett , vol.45 , pp. 417
- Gracias, V.¹ Moore, J.D.² Djuric, S.W.³

15
- 4544317487
- (b) Xiang, Z.; Luo, T.; Lu, K.; Cui, J.; Shi, X.; Fathi, R.; Chen, J.; Yang, Z. Org. Lett. 2004, 6, 3155.
- (2004) Org. Lett , vol.6 , pp. 3155
- Xiang, Z.¹ Luo, T.² Lu, K.³ Cui, J.⁴ Shi, X.⁵ Fathi, R.⁶ Chen, J.⁷ Yang, Z.⁸

16
- 3142683044
- (a) Krelaus, R.; Westermann, B. Tetrahedron Lett. 2004, 45, 5987.
- (2004) Tetrahedron Lett , vol.45 , pp. 5987
- Krelaus, R.¹ Westermann, B.²

17
- 11844269831
- (b) Kazmaeir, U.; Hebach, C.; Watzke, A.; Maier, S.; Mues, H.; Huch, V. Org. Biomol. Chem. 2005, 3, 136.
- (2005) Org. Biomol. Chem , vol.3 , pp. 136
- Kazmaeir, U.¹ Hebach, C.² Watzke, A.³ Maier, S.⁴ Mues, H.⁵ Huch, V.⁶

18
- 0344514145
- (c) Sello, J. K.; Andreana, P. R.; Lee, D.; Schreiber, S. L. Org. Lett. 2003, 5, 4125.
- (2003) Org. Lett , vol.5 , pp. 4125
- Sello, J.K.¹ Andreana, P.R.² Lee, D.³ Schreiber, S.L.⁴

19
- 0141741234
- (d) Banfi, L.; Basso, A.; Guanti, G.; Riva, R. Tetrahedron Lett. 2003, 44, 7655.
- (2003) Tetrahedron Lett , vol.44 , pp. 7655
- Banfi, L.¹ Basso, A.² Guanti, G.³ Riva, R.⁴

20
- 0037932800
- (e) Beck, B.; Larbig, G.; Mejat, B.; Magnin-Lachaux, M.; Picard, A.; Herdtweck, E.; Dömling, A. Org. Lett. 2003, 5, 1047.
- (2003) Org. Lett , vol.5 , pp. 1047
- Beck, B.¹ Larbig, G.² Mejat, B.³ Magnin-Lachaux, M.⁴ Picard, A.⁵ Herdtweck, E.⁶ Dömling, A.⁷

21
- 0036925124
- (a) Faggi, C.; Marcaccini, S.; Pepino, R.; Pozo, M. C. Synthesis 2002, 2756.
- (2002) Synthesis , pp. 2756
- Faggi, C.¹ Marcaccini, S.² Pepino, R.³ Pozo, M.C.⁴

22
- 11144290645
- (b) Marcaccini, S.; Miliciani, M.; Pepino, R. Tetrahedron Lett. 2005, 46, 711.
- (2005) Tetrahedron Lett , vol.46 , pp. 711
- Marcaccini, S.¹ Miliciani, M.² Pepino, R.³

23
- 0037170146
- (c) Nixey, T.; Tempest, P.; Hulme, C. Tetrahedron Lett. 2002, 43, 1637.
- (2002) Tetrahedron Lett , vol.43 , pp. 1637
- Nixey, T.¹ Tempest, P.² Hulme, C.³

24
- 0034693119
- (a) Pourashraf, M.; Delair, P.; Rasmussen, M. O.; Greene, A. E. J. Org. Chem. 2000, 65, 6966.
- (2000) J. Org. Chem , vol.65 , pp. 6966
- Pourashraf, M.¹ Delair, P.² Rasmussen, M.O.³ Greene, A.E.⁴

25
- 0036353745
- (b) Cossy, J.; Willis, C.; Bellosta, V.; Jalmes, L. S. Synthesis 2002, 951.
- (2002) Synthesis , pp. 951
- Cossy, J.¹ Willis, C.² Bellosta, V.³ Jalmes, L.S.⁴

26
- 0033051156
- (c) Diederich, M.; Nubbemeyer, U. Synthesis 1999, 286.
- (1999) Synthesis , pp. 286
- Diederich, M.¹ Nubbemeyer, U.²

27
- 0033605165
- (d) Chalard, P.; Remuson, R.; Mialhe, Y. G.; Gramain, J. C.; Canet, I. Tetrahedron Lett. 1999, 40, 1661.
- (1999) Tetrahedron Lett , vol.40 , pp. 1661
- Chalard, P.¹ Remuson, R.² Mialhe, Y.G.³ Gramain, J.C.⁴ Canet, I.⁵

28
- 0035888827
- (e) Park, S. H.; Kang, H. J.; Ko, S.; Park, S.; Chang, S. Tetrahedron: Asymmetry 2001, 12, 2621.
- (2001) Tetrahedron: Asymmetry , vol.12 , pp. 2621
- Park, S.H.¹ Kang, H.J.² Ko, S.³ Park, S.⁴ Chang, S.⁵

29
- 14544300945
- (f) Carroll, A. R.; Arumugan, G.; Quinn, R. J.; Redburn, J.; Guymer, G.; Grimshaw, P. J. Org. Chem. 2005, 70, 1889.
- (2005) J. Org. Chem , vol.70 , pp. 1889
- Carroll, A.R.¹ Arumugan, G.² Quinn, R.J.³ Redburn, J.⁴ Guymer, G.⁵ Grimshaw, P.⁶

30
- 0026594071
- (a) Gubin, J.; Lucchetti, J.; Mahaux, J.; Nisato, D.; Rosseels, G.; Clinet, M.; Polster, P.; Chatelain, P. J. Med. Chem. 1992, 35, 981.
- (1992) J. Med. Chem , vol.35 , pp. 981
- Gubin, J.¹ Lucchetti, J.² Mahaux, J.³ Nisato, D.⁴ Rosseels, G.⁵ Clinet, M.⁶ Polster, P.⁷ Chatelain, P.⁸

31
- 0027285920
- (b) Gubin, J.; Vogelaer, H.; Inion, H.; Houben, C.; Lucchetti, J.; Mahaux, J.; Rosseels, G.; Peiren, M.; Clinet, M.; Polster, P.; Chatelain, P. J. Med Chem. 1993, 36, 1425.
- (1993) J. Med Chem , vol.36 , pp. 1425
- Gubin, J.¹ Vogelaer, H.² Inion, H.³ Houben, C.⁴ Lucchetti, J.⁵ Mahaux, J.⁶ Rosseels, G.⁷ Peiren, M.⁸ Clinet, M.⁹ Polster, P.¹⁰ Chatelain, P.¹¹

32
- 0142250758
- (c) Gupta, S. P.; Mathur, A. N.; Nagappa, A. N.; Kumar, D.; Kumaran, S. Eur. J. Med. Chem. 2003, 38, 867.
- (2003) Eur. J. Med. Chem , vol.38 , pp. 867
- Gupta, S.P.¹ Mathur, A.N.² Nagappa, A.N.³ Kumar, D.⁴ Kumaran, S.⁵

33
- 0026001925
- (d) Olden, K.; Breton, P.; Grzegorzewski, K.; Yasuda, Y.; Gause, B. L. Pharmacol. Ther. 1991, 50, 285.
- (1991) Pharmacol. Ther , vol.50 , pp. 285
- Olden, K.¹ Breton, P.² Grzegorzewski, K.³ Yasuda, Y.⁴ Gause, B.L.⁵

34
- 0023645052
- (e) Ahrens, P. B.; Ankel, H. J. Biol. Chem. 1987, 262, 7575.
- (1987) J. Biol. Chem , vol.262 , pp. 7575
- Ahrens, P.B.¹ Ankel, H.²

35
- 0022368666
- (f) Sasak, V. W.; Ordovas, J. M.; Elbein, A. D.; Berninger, R. W. Biochem. J. 1985, 232, 759.
- (1985) Biochem. J , vol.232 , pp. 759
- Sasak, V.W.¹ Ordovas, J.M.² Elbein, A.D.³ Berninger, R.W.⁴

36
- 0022445051
- (g) Dennis, J. W. Cancer Res. 1986, 46, 5131.
- (1986) Cancer Res , vol.46 , pp. 5131
- Dennis, J.W.¹

37
- 85178961265
- (a) Tschitschibabin, A. E. Ber. Dtsch. Chem. Ges. 1927, 60, 1607.
- (1927) Ber. Dtsch. Chem. Ges , vol.60 , pp. 1607
- Tschitschibabin, A.E.¹

38
- 0033214880
- (b) Katritzky, A. R.; Qui, G.; Yang, B.; He, H. Y. J. Org. Chem. 1999, 64, 7618.
- (1999) J. Org. Chem , vol.64 , pp. 7618
- Katritzky, A.R.¹ Qui, G.² Yang, B.³ He, H.Y.⁴

39
- 0347606904
- (a) Scholtz, M. Ber. Dtsch. Chem. Ges. 1912, 45, 734.
- (1912) Ber. Dtsch. Chem. Ges , vol.45 , pp. 734
- Scholtz, M.¹

40
- 25444508466
- (b) Boekelheide, V.; Windgassen, R. J. Jr. J. Am. Chem. Soc. 1959, 81, 1456.
- (1959) J. Am. Chem. Soc , vol.81 , pp. 1456
- Boekelheide, V.¹ Windgassen Jr., R.J.²

41
- 33751385568
- (a) Padwa, A.; Austin, D. J.; Precedo, L.; Zhi, L. J. Org. Chem. 1993, 58, 1144.
- (1993) J. Org. Chem , vol.58 , pp. 1144
- Padwa, A.¹ Austin, D.J.² Precedo, L.³ Zhi, L.⁴

42
- 37049074960
- (b) Wei, X.; Hu, Y.; Li, T.; Hu, H. J. Chem. Soc., Perkin Trans. 1 1993, 2487.
- (1993) J. Chem. Soc., Perkin Trans. 1 , pp. 2487
- Wei, X.¹ Hu, Y.² Li, T.³ Hu, H.⁴

43
- 2142652134
- (c) Siriwardana, A. I.; Nakamura, I.; Yamamoto, Y. J. Org. Chem. 2004, 69, 3202.
- (2004) J. Org. Chem , vol.69 , pp. 3202
- Siriwardana, A.I.¹ Nakamura, I.² Yamamoto, Y.³

44
- 37049138266
- (d) Acheson, R. M.; Robinson, D. A. J. Chem. Soc. 1968, 1633.
- (1968) J. Chem. Soc , pp. 1633
- Acheson, R.M.¹ Robinson, D.A.²

45
- 0039067331
- (e) Dinculescu, A.; Balaban, T. S.; Balaban, A. T. Tetrahedron Lett. 1987, 28, 3145.
- (1987) Tetrahedron Lett , vol.28 , pp. 3145
- Dinculescu, A.¹ Balaban, T.S.² Balaban, A.T.³

46
- 0033745431
- (f) Zhang, L.; Liang, F.; Sun, L.; Hu, Y.; Hu, H. Synthesis 2000, 1733.
- (2000) Synthesis , pp. 1733
- Zhang, L.¹ Liang, F.² Sun, L.³ Hu, Y.⁴ Hu, H.⁵

47
- 2542421781
- (g) Fang, X.; Wu, Y. M.; Deng, J.; Wang, S. W. Tetrahedron 2004, 60, 5487.
- (2004) Tetrahedron , vol.60 , pp. 5487
- Fang, X.¹ Wu, Y.M.² Deng, J.³ Wang, S.W.⁴

48
- 0042566349
- Bora, U.; Saikia, A.; Boruah, R. C. Org. Lett. 2003, 5, 435.
- (2003) Org. Lett , vol.5 , pp. 435
- Bora, U.¹ Saikia, A.² Boruah, R.C.³

49
- 33745788132
- (a) Bedjeguelal, K.; Bienaymé, H.; Poigny, S.; Schmitt, Ph.; Tam, E. QSAR Comb. Sci. 2006, 25, 504.
- (2006) QSAR Comb. Sci , vol.25 , pp. 504
- Bedjeguelal, K.¹ Bienaymé, H.² Poigny, S.³ Schmitt, P.⁴ Tam, E.⁵

50
- 28844435263
- (b) Tielmann, P.; Hoenke, C. Tetrahedron Lett. 2006, 47, 261.
- (2006) Tetrahedron Lett , vol.47 , pp. 261
- Tielmann, P.¹ Hoenke, C.²

51
- 0033544818
- (c) Goff, D. A. Tetrahedron Lett. 1999, 40, 8741.
- (1999) Tetrahedron Lett , vol.40 , pp. 8741
- Goff, D.A.¹

52
- 0035795047
- For recent uses of chloroacetic acid in Ugi reactions, see: a
- For recent uses of chloroacetic acid in Ugi reactions, see: (a) Marcaccini, S.; Pepino, R.; Cruz Pozo, M. Tetrahedron Lett. 2001, 42, 2727.
- (2001) Tetrahedron Lett , vol.42 , pp. 2727
- Marcaccini, S.¹ Pepino, R.² Cruz Pozo, M.³

53
- 33750218780
- (b) El Kaim, L.; Grimaud, L.; Miranda, L. D.; Vieu, E. Tetrahedron Lett. 2006, 47, 8259.
- (2006) Tetrahedron Lett , vol.47 , pp. 8259
- El Kaim, L.¹ Grimaud, L.² Miranda, L.D.³ Vieu, E.⁴

54
- 33847027672
- For similar oxidations, see: ref. 10a,c and ref. 11
- For similar oxidations, see: ref. 10a,c and ref. 11.

55
- 33847076199
- Typical Procedure (Given for 7c, Table 1, Anisaldehyde 1a (5 mmol, 608 μL, propargylamine (1 equiv, 343 μL, chloroacetic acid (1 equiv, 472 mg) and cyclohexyl isocyanide 2b (1 equiv, 622 μL) were added to MeOH (5 mL) and the mixture stirred overnight at r.t. The crude product was purified by flash chromatography using CH2Cl2 to give 1.41 g of 3b (70, To the chloro derivative 3b (3.2 mmol) in EtOH (3 mL) was added 4-picoline (2 equiv, 0.52 mL) and the mixture stirred at 50°C for 24 h. EtOH was evaporated, the crude product (1.6 mmol) was then added to 1-iodo-4-nitrobenzene (6b, 1.1 equiv, 876 mg) in a mixture THF-i-Pr2NH (1:1,6 mL, Then, Pd(OAc)2 (0.04 equiv, 28 mg, CuI (0.08 equiv, 48 mg) and PPh3 (0.08 equiv, 66 mg) were added and the mixture was stirred for 2 d. Extraction, evaporation and flash chromatography using Et2O-PE (50: 50) afford 590 mg of 7c
- 5: 552.2373; found: 552.2385.

56
- 2442621123
- (a) Dubowchik, G. M.; Michne, J. A.; Zuev, D. Bioorg. Med. Chem. Lett. 2004, 14, 3147.
- (2004) Bioorg. Med. Chem. Lett , vol.14 , pp. 3147
- Dubowchik, G.M.¹ Michne, J.A.² Zuev, D.³

57
- 0035808917
- (b) Kang, K. H.; Pae, A. N.; Choi, K.; Cho, Y. S.; Chung, B. Y.; Lee, J. E.; Jung, S. H.; Koh, H. Y.; Lee, H. Tetrahedron Lett. 2001, 42, 1057.
- (2001) Tetrahedron Lett , vol.42 , pp. 1057
- Kang, K.H.¹ Pae, A.N.² Choi, K.³ Cho, Y.S.⁴ Chung, B.Y.⁵ Lee, J.E.⁶ Jung, S.H.⁷ Koh, H.Y.⁸ Lee, H.⁹

58
- 33847055457
- 2O and filtration gave pyridinium 5 which was further treated as shown for 7c.
- 2O and filtration gave pyridinium 5 which was further treated as shown for 7c.

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.