SCOPUS 정보 검색 플랫폼

Synlett

Volumn , Issue 3, 2007, Pages 500-502

New Ugi/Pictet-Spengler multicomponent formation of polycyclic diketopiperazines from isocyanides and α-keto acids

(4) El Kaim, Laurent a Gageat, Mathilde a Gaultier, Laetitia a Grimaud, Laurence a

a Ecole Nationale Superieure de Techniques Avancees (France)

Author keywords

Diketopiperazine; Isocyanide; Multicomponent reaction; Pictet Spengler; Ugi

Indexed keywords

1,4 DIKETOPIPERAZINE; 2 OXOACID; 2,5 PIPERAZINEDIONE; 6 HYDROXYPIPERAZINE; CYANIDE; DIPEPTIDE; ISOCYANIDE; PIPERAZINE DERIVATIVE; PIPERAZINEDIONE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CYCLIZATION; PICTET SPENGLER REACTION; POLYMERIZATION;

EID: 33847396935 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2007-968026 Document Type: Article

Times cited : (52)

References (27)

1
- 0030599282
- (a) Cui, C.-B.; Kakeya, H.; Osada, H. Tetrahedron 1996, 52, 12651.
- (1996) Tetrahedron , vol.52 , pp. 12651
- Cui, C.-B.¹ Kakeya, H.² Osada, H.³

2
- 0030036459
- (b) Cui, C.-B.; Kakeya, H.; Osada, H. J. Antibiot. 1996, 49, 534.
- (1996) J. Antibiot , vol.49 , pp. 534
- Cui, C.-B.¹ Kakeya, H.² Osada, H.³

3
- 0029894647
- (c) Charlton, P. A.; Faint, R. W.; Bent, F.; Bryans, J.; Chicarelli-Robinson, I.; Mackie, I.; Machin, S.; Bevan, P. Thromb. Haemost. 1996, 75, 808.
- (1996) Thromb. Haemost , vol.75 , pp. 808
- Charlton, P.A.¹ Faint, R.W.² Bent, F.³ Bryans, J.⁴ Chicarelli-Robinson, I.⁵ Mackie, I.⁶ Machin, S.⁷ Bevan, P.⁸

4
- 0028171012
- (d) Funabashi, Y.; Horiguchi, T.; Iinuma, S.; Tanida, S.; Harada, S. J. Antibiot. 1994, 47, 1202.
- (1994) J. Antibiot , vol.47 , pp. 1202
- Funabashi, Y.¹ Horiguchi, T.² Iinuma, S.³ Tanida, S.⁴ Harada, S.⁵

5
- 0028878426
- (e) Barrow, C. J.; Musza, L. L.; Cooper, R. Bioorg. Med. Chem. Lett. 1995, 5, 377.
- (1995) Bioorg. Med. Chem. Lett , vol.5 , pp. 377
- Barrow, C.J.¹ Musza, L.L.² Cooper, R.³

6
- 0037156593
- Dinsmore, C. J.; Beshore, D. C. Tetrahedron 2002, 58, 3297.
- (2002) Tetrahedron , vol.58 , pp. 3297
- Dinsmore, C.J.¹ Beshore, D.C.²

7
- 2542509173
- For general reviews on isocyanide-based multicomponent reactions, see: a
- For general reviews on isocyanide-based multicomponent reactions, see: (a) 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

8
- 31544434530
- (b) Dömling, A. Chem. Rev. 2006, 106, 17.
- (2006) Chem. Rev , vol.106 , pp. 17
- Dömling, A.¹

9
- 0037018444
- (a) Kennedy, A. L.; Fryer, A. M.; Josey, J. A. Org. Lett. 2002, 7, 1167.
- (2002) Org. Lett , vol.7 , pp. 1167
- Kennedy, A.L.¹ Fryer, A.M.² Josey, J.A.³

10
- 33845376189
- (b) Boehm, J. C.; Kingsbury, W. D. J. Org. Chem. 1986, 51, 2307.
- (1986) J. Org. Chem , vol.51 , pp. 2307
- Boehm, J.C.¹ Kingsbury, W.D.²

11
- 0019851849
- (c) Fukuyama, T.; Robins, B. D.; Sachleben, R. A. Tetrahedron Lett. 1981, 22, 4155.
- (1981) Tetrahedron Lett , vol.22 , pp. 4155
- Fukuyama, T.¹ Robins, B.D.² Sachleben, R.A.³

12
- 0037067104
- (d) Endo, A.; Yanagisawa, A.; Abe, M.; Tohma, S.; Kan, T.; Fukuyama, T. J. Am. Chem. Soc. 2002, 124, 6552.
- (2002) J. Am. Chem. Soc , vol.124 , pp. 6552
- Endo, A.¹ Yanagisawa, A.² Abe, M.³ Tohma, S.⁴ Kan, T.⁵ Fukuyama, T.⁶

13
- 33745807624
- (e) Habashita, H.; Kokubo, M.; Hamano, S.; Hamanaka, N.; Toda, M.; Shibayama, S.; Tada, H.; Sagawa, K.; Fukushima, D.; Maeda, K.; Mitsuya, H. J. Med. Chem. 2006, 49, 4140.
- (2006) J. Med. Chem , vol.49 , pp. 4140
- Habashita, H.¹ Kokubo, M.² Hamano, S.³ Hamanaka, N.⁴ Toda, M.⁵ Shibayama, S.⁶ Tada, H.⁷ Sagawa, K.⁸ Fukushima, D.⁹ Maeda, K.¹⁰ Mitsuya, H.¹¹

14
- 0032485439
- (a) Hulme, C.; Morrissette, M. M.; Volz, F. A.; Burns, C. J. Tetrahedron Lett. 1998, 39, 1113.
- (1998) Tetrahedron Lett , vol.39 , pp. 1113
- Hulme, C.¹ Morrissette, M.M.² Volz, F.A.³ Burns, C.J.⁴

15
- 0033575465
- (b) Hulme, C.; Cherrier, M.-P. Tetrahedron Lett. 1999, 40, 5295.
- (1999) Tetrahedron Lett , vol.40 , pp. 5295
- Hulme, C.¹ Cherrier, M.-P.²

16
- 0031000559
- Szardenings, A. K.; Burkoth, T. S.; Lu, H. H.; Tien, D. W.; Campbell, D. A. Tetrahedron 1997, 53, 6573.
- (1997) Tetrahedron , vol.53 , pp. 6573
- Szardenings, A.K.¹ Burkoth, T.S.² Lu, H.H.³ Tien, D.W.⁴ Campbell, D.A.⁵

17
- 0345871009
- Cho, S.; Keum, G.; Soon, B. K.; Han, S. Y.; Kim, Y. Mol. Diversity 2003, 6, 283.
- (2003) Mol. Diversity , vol.6 , pp. 283
- Cho, S.¹ Keum, G.² Soon, B.K.³ Han, S.Y.⁴ Kim, Y.⁵

18
- 0035795047
- Marcaccini, S.; Pepino, R.; Pozo, C. Tetrahedron Lett. 2001, 42, 2727.
- (2001) Tetrahedron Lett , vol.42 , pp. 2727
- Marcaccini, S.¹ Pepino, R.² Pozo, C.³

19
- 20344397439
- Sollis, S. L. J. Org. Chem. 2005, 70, 4735.
- (2005) J. Org. Chem , vol.70 , pp. 4735
- Sollis, S.L.¹

20
- 4243241249
- For a review, see
- For a review, see: Cox, E. D.; Cook, J. M. Chem. Rev. 1995, 95, 1797.
- (1995) Chem. Rev , vol.95 , pp. 1797
- Cox, E.D.¹ Cook, J.M.²

21
- 0034625424
- For a review, see
- For a review, see: Speckamp, W. N.; Moolenaar, M. J. Tetrahedron 2000, 56, 3817.
- (2000) Tetrahedron , vol.56 , pp. 3817
- Speckamp, W.N.¹ Moolenaar, M.J.²

22
- 33847414455
- Typical Procedure (Given for 6a, To a solution of 124 mg of o-nitrobenzaldehyde 2a (0.82 mmol, 1 equiv)and 60 mg of butylamine 3a (0.82 mmol, 1 equiv) in MeOH (800 μL, 1 M) were added 157 mg of homoveratryl isocyanide(4a, 0.82 mmol,-1 equiv) and 57 μL of pyruvic acid (1a, 0.82 mmol, 1 equiv) under inert argon atmosphere. The mixture was then stirred at r.t. during 2 h. After concentration under reduced pressure, the crude product was dissolved in 4 mL of TFA (0.2 M) and stirred at r.t. for 1 h. Flash chromatography (50-100% Et2O-petroleum ether gradient) afforded the desired diketopiperazine in a 69% overall yield as a mixture of two diastereomers in a 1:1.2 ratio. Spectroscopic Data for DKP 6a: Major diastereomer: 1H NMR (400 MHz, CDCl3, δ, 7.94 (d, J, 7.8 Hz, 1 H, 7.78 (s, 1 H, 7.40 (dt, J, 3.8, 7.6 Hz, 2 H, 6.74 (d, J, 7.6 Hz, 1 H, 6.55 (s, 1 H, 6.25 (s, 1 H, 4.69 q, J, 7.8 H
- 3: 467.2056; found: 467.2052.

23
- 3142770548
- (a) Pirrung, M. C.; Sarma, K. D. Synlett 2004, 1425.
- (2004) Synlett , pp. 1425
- Pirrung, M.C.¹ Sarma, K.D.²

24
- 0030873527
- (b) Harriman, G. C. B. Tetrahedron Lett. 1997, 38, 5591.
- (1997) Tetrahedron Lett , vol.38 , pp. 5591
- Harriman, G.C.B.¹

25
- 0037170146
- 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

26
- 33744942880
- Sanudo, M.; Marcaccini, S.; Basurto, S.; Torroba, T. J. Org. Chem. 2006, 71, 4578.
- (2006) J. Org. Chem , vol.71 , pp. 4578
- Sanudo, M.¹ Marcaccini, S.² Basurto, S.³ Torroba, T.⁴

27
- 0035810396
- Zawadzka, A.; Leniewski, A.; Maurin, J. K.; Wojtasiewicz, K.; Czarnocki, Z. Org. Lett. 2001, 3, 997.
- (2001) Org. Lett , vol.3 , pp. 997
- Zawadzka, A.¹ Leniewski, A.² Maurin, J.K.³ Wojtasiewicz, K.⁴ Czarnocki, Z.⁵

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.