SCOPUS 정보 검색 플랫폼

Synlett

Volumn , Issue 8, 2008, Pages 1133-1136

Isocyanide addition to acylphosphonates: A formal Passerini reaction of acyl chlorides

(3) Coffinier, Didier a El Kaim, Laurent a Grimaud, Laurence a

a Ecole Nationale Superieure de Techniques Avancees (France)

Author keywords

Isocyanide; Multicomponent reaction; Passerini reaction; Phosphonate

Indexed keywords

ALDEHYDE; CARBOXYLIC ACID DERIVATIVE; CHLORIDE; PHOSPHONIC ACID DERIVATIVE;

ADDITION REACTION; ARTICLE; CHEMICAL STRUCTURE; QUANTITATIVE ANALYSIS; REACTION ANALYSIS;

EID: 44349133262 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2008-1072726 Document Type: Article

Times cited : (13)

References (43)

1
- 26844537872
- For recent reviews, see: a
- For recent reviews, see: (a) Banfi, L.; Riva, R. Org. React. (N. Y.) 2005, 65, 1.
- (2005) Org. React. (N. Y.) , 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
- 84958690531
- Nef, J. U. Justus Liebigs Ann. Chem. 1892, 270, 267.
- (1892) Justus Liebigs Ann. Chem , vol.270 , pp. 267
- Nef, J.U.¹

9
- 84971052020
- (a) Ugi, I.; Fetzer, U. Chem. Ber. 1961, 94, 1116.
- (1961) Chem. Ber , vol.94 , pp. 1116
- Ugi, I.¹ Fetzer, U.²

10
- 0000433901
- (b) Westling, M.; Smith, R.; Livinghouse, T. J. Org. Chem. 1986, 51, 1159.
- (1986) J. Org. Chem , vol.51 , pp. 1159
- Westling, M.¹ Smith, R.² Livinghouse, T.³

11
- 0026749040
- (c) Lee, C. H.; Westling, M.; Livinghouse, T.; Williams, A. C. J. Am. Chem. Soc. 1992, 114, 4089.
- (1992) J. Am. Chem. Soc , vol.114 , pp. 4089
- Lee, C.H.¹ Westling, M.² Livinghouse, T.³ Williams, A.C.⁴

12
- 0033551720
- (d) Livinghouse, T. Tetrahedron 1999, 55, 9947.
- (1999) Tetrahedron , vol.55 , pp. 9947
- Livinghouse, T.¹

13
- 0024371464
- (e) VanWangenen, B. C.; Cardellina, J. H. Tetrahedron Lett. 1989, 30, 3605.
- (1989) Tetrahedron Lett , vol.30 , pp. 3605
- VanWangenen, B.C.¹ Cardellina, J.H.²

14
- 44349094060
- (f) Adlington, R. M.; Barrett, A. G. M. Tetrahedron 1981, 37, 3935.
- (1981) Tetrahedron , vol.37 , pp. 3935
- Adlington, R.M.¹ Barrett, A.G.M.²

15
- 0242266536
- (a) Chen, J. J.; Deshpande, S. V. Tetrahedron Lett. 2003, 44, 8873.
- (2003) Tetrahedron Lett , vol.44 , pp. 8873
- Chen, J.J.¹ Deshpande, S.V.²

16
- 44349135398
- See also: ref. 3a and 3f
- (b) See also: ref. 3a and 3f.

17
- 0032499118
- El Kaim, L.; Pinot-Périgord, E. Tetrahedron 1998, 54, 3799.
- (1998) Tetrahedron , vol.54 , pp. 3799
- El Kaim, L.¹ Pinot-Périgord, E.²

18
- 6444223724
- (a) Oaksmith, J. M.; Peters, U.; Ganem, B. J. Am. Chem. Soc. 2004, 126, 13606.
- (2004) J. Am. Chem. Soc , vol.126 , pp. 13606
- Oaksmith, J.M.¹ Peters, U.² Ganem, B.³

19
- 2442485083
- (b) Richter, M.; Herrmann, C.; Augustin, M. J. Prakt. Chem. 1980, 322, 434.
- (1980) J. Prakt. Chem , vol.322 , pp. 434
- Richter, M.¹ Herrmann, C.² Augustin, M.³

20
- 25444510404
- El Kaim, L.; Gaultier, L.; Grimaud, L.; Dos Santos, A. Synlett 2005, 2335.
- (2005) Synlett , pp. 2335
- El Kaim, L.¹ Gaultier, L.² Grimaud, L.³ Dos Santos, A.⁴

21
- 0028857767
- (a) Patel, D. V.; Rielly-Gauvin, K.; Ryono, D. E.; Free, C. A.; Rogers, W. L.; Smith, S. A.; DeForrest, J. M.; Oehl, R. S.; Petrillo, E. W. J. Med. Chem. 1995, 38, 4557.
- (1995) J. Med. Chem , vol.38 , pp. 4557
- Patel, D.V.¹ Rielly-Gauvin, K.² Ryono, D.E.³ Free, C.A.⁴ Rogers, W.L.⁵ Smith, S.A.⁶ DeForrest, J.M.⁷ Oehl, R.S.⁸ Petrillo, E.W.⁹

22
- 0033968380
- (b) Sun, F. Y.; Schmid, E.; Baumgartner, A.; Adler, T.-D. Mutagenesis 2000, 15, 17.
- (2000) Mutagenesis , vol.15 , pp. 17
- Sun, F.Y.¹ Schmid, E.² Baumgartner, A.³ Adler, T.-D.⁴

23
- 33646717586
- (c) Chevrier, C.; Le Nouen, D.; Defoin, A.; Tarnus, C. Eur. J. Org. Chem. 2006, 2384.
- (2006) Eur. J. Org. Chem , pp. 2384
- Chevrier, C.¹ Le Nouen, D.² Defoin, A.³ Tarnus, C.⁴

24
- 84988121926
- For a review see
- For a review see: Pudovik, A. N.; Konovalova, I. V. Synthesis 1979, 81.
- (1979) Synthesis , pp. 81
- Pudovik, A.N.¹ Konovalova, I.V.²

25
- 25444483018
- (a) Pudovik, A. N.; Konovalova, I. V.; Dedova, L. V. Zh. Obshch. Khim. 1964, 34, 2902.
- (1964) Zh. Obshch. Khim , vol.34 , pp. 2902
- Pudovik, A.N.¹ Konovalova, I.V.² Dedova, L.V.³

26
- 25444515623
- (b) Polezhaeva, N. A.; Ovodova, O. V.; Litivinov, I. A.; El'shina, E. V.; Naumov, V. A.; Arbuzov, B. A. Izv. Akad. Nauk. SSSR, Ser. Khim. 1986, 8, 1860.
- (1986) Izv. Akad. Nauk. SSSR, Ser. Khim , vol.8 , pp. 1860
- Polezhaeva, N.A.¹ Ovodova, O.V.² Litivinov, I.A.³ El'shina, E.V.⁴ Naumov, V.A.⁵ Arbuzov, B.A.⁶

27
- 25444473334
- (c) Fokin, A. V.; Studnev, Y. N.; Rapkin, A. I.; Pasevina, K. I.; Verenikin, O. V.; Kolomiets, A. F. Izv. Akad. Nauk. SSSR, Ser. Khim. 1981, 7, 1655.
- (1981) Izv. Akad. Nauk. SSSR, Ser. Khim , vol.7 , pp. 1655
- Fokin, A.V.¹ Studnev, Y.N.² Rapkin, A.I.³ Pasevina, K.I.⁴ Verenikin, O.V.⁵ Kolomiets, A.F.⁶

28
- 37049126423
- (d) Gallagher, M. J.; Jenkins, I. D. J. Chem. Soc. C 1969, 2605.
- (1969) J. Chem. Soc. C , pp. 2605
- Gallagher, M.J.¹ Jenkins, I.D.²

29
- 84982063298
- (a) Hammerschmidt, F.; Schneyder, E.; Zbiral, E. Chem. Ber. 1980, 113, 3891.
- (1980) Chem. Ber , vol.113 , pp. 3891
- Hammerschmidt, F.¹ Schneyder, E.² Zbiral, E.³

30
- 0002745369
- (b) Tromelin, A.; El Manouni, D.; Burgada, R. Phosphorus Sulfur Relat. Elem. 1986, 27, 301.
- (1986) Phosphorus Sulfur Relat. Elem , vol.27 , pp. 301
- Tromelin, A.¹ El Manouni, D.² Burgada, R.³

31
- 0029084326
- (c) Ruel, R.; Bouvier, J.-P.; Young, R. N. J. Org. Chem. 1995, 60, 5209.
- (1995) J. Org. Chem , vol.60 , pp. 5209
- Ruel, R.¹ Bouvier, J.-P.² Young, R.N.³

32
- 0001137761
- (d) Barthel, W. F.; Alexander, B. H.; Giang, P. A.; Hall, S. A. J. Am. Chem. Soc. 1955, 77, 2424.
- (1955) J. Am. Chem. Soc , vol.77 , pp. 2424
- Barthel, W.F.¹ Alexander, B.H.² Giang, P.A.³ Hall, S.A.⁴

33
- 22944432525
- (e) Bausch, C. C.; Johnson, J. S. Adv. Synth. Catal. 2005, 347, 1207.
- (2005) Adv. Synth. Catal , vol.347 , pp. 1207
- Bausch, C.C.¹ Johnson, J.S.²

34
- 44349177207
- (a) Pudovik, A. N.; Konovalova, I. V. J. Gen. Chem. USSR (Engl. Transl.) 1963, 33, 3026.
- (1963) J. Gen. Chem. USSR (Engl. Transl.) , vol.33 , pp. 3026
- Pudovik, A.N.¹ Konovalova, I.V.²

35
- 33947473661
- (b) Fitch, S. J.; Moedritzer, K. J. Am. Chem. Soc. 1962, 84, 1876.
- (1962) J. Am. Chem. Soc , vol.84 , pp. 1876
- Fitch, S.J.¹ Moedritzer, K.²

36
- 0342516044
- (c) Hammerschmidt, F.; Zbiral, E. Monatsh. Chem. 1980, 111, 1015.
- (1980) Monatsh. Chem , vol.111 , pp. 1015
- Hammerschmidt, F.¹ Zbiral, E.²

37
- 0023178655
- (d) Nguyen, L. M.; Niesor, E.; Bentzen, C. J. Med. Chem. 1987, 30, 1426.
- (1987) J. Med. Chem , vol.30 , pp. 1426
- Nguyen, L.M.¹ Niesor, E.² Bentzen, C.³

38
- 33947463282
- (a) Hall, L. A. R.; Stephens, C. W.; Drysdale, J. J. J. Am. Chem. Soc. 1957, 79, 1768.
- (1957) J. Am. Chem. Soc , vol.79 , pp. 1768
- Hall, L.A.R.¹ Stephens, C.W.² Drysdale, J.J.³

39
- 28744457017
- (b) Demir, A. S.; Reis, O.; Igdir, A. C.; Esiringü, I.; Eymür, S. J. Org. Chem. 2005, 70, 10584.
- (2005) J. Org. Chem , vol.70 , pp. 10584
- Demir, A.S.¹ Reis, O.² Igdir, A.C.³ Esiringü, I.⁴ Eymür, S.⁵

40
- 34548791676
- (c) Demir, A. S.; Reis, B.; Reis, O.; Eymür, S.; Göllü, M.; Tural, S.; Saglam, G. J. Org. Chem. 2007, 72, 7439.
- (2007) J. Org. Chem , vol.72 , pp. 7439
- Demir, A.S.¹ Reis, B.² Reis, O.³ Eymür, S.⁴ Göllü, M.⁵ Tural, S.⁶ Saglam, G.⁷

41
- 34548772904
- (d) Demir, A. S.; Reis, O.; Esiringu, I.; Reis, B.; Baris, S. Tetrahedron 2007, 63, 160.
- (2007) Tetrahedron , vol.63 , pp. 160
- Demir, A.S.¹ Reis, O.² Esiringu, I.³ Reis, B.⁴ Baris, S.⁵

42
- 33845610068
- Demir, A. S.; Reis, O.; Kayalar, M.; Eymur, S.; Reis, B. Synlett 2006, 3329.
- (2006) Synlett , pp. 3329
- Demir, A.S.¹ Reis, O.² Kayalar, M.³ Eymur, S.⁴ Reis, B.⁵

43
- 44349134814
- General Procedure for the Formation of Phosphonate 5: To acyl chloride 1 (2 mmol) was added neat trialkyl phosphite (1 equiv, The mixture was stirred under argon for 30 min. Toluene (1 M, isocyanide (1 equiv) and carboxylic acid (1 equiv) were then successively added. The mixture was stirred for 24 h under argon at r.t, for alkyl acyl chlorides) or at 80°C (for aromatic acyl chlorides, The solvent was then removed under reduced pressure to afford Passerini products after purification by flash column chromatography on silica gel. Data for 5a: mp 72-74°C; R f (EtOAc-PE, 50:50, 0.1. 1H NMR (400 MHz, CDCl 3, δ, 7.26-7.33 (m, 2 H, 7.18-7.24 (m, 3 H, 6.73 (d, J, 8.3 Hz, 1 H, 3.84-3.88 (m, 1 H, 3.88 (d, JH-P, 10.8 Hz, 3 H, 3.84 (d, JH-P, 10.6 Hz, 3 H, 2.69-2.80 (m, 1 H, 2.56-2.69 (m, 3 H, 2.18 (s, 3 H, 1.91-1.99 (m, 2 H, 1.68-1.78 (m, 2 H, 1.59-1.66 m, 1
- 5P: 369.1705; found: 369.1700.

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.