SCOPUS 정보 검색 플랫폼

Synlett

Volumn , Issue 14, 2008, Pages 2142-2146

Synthesis of bispyrrolidines by radical cyclisation of diallylamines using phosphorus hydrides

(2) Parsons, Andrew F a Wright, Anthony a

a UNIVERSITY OF YORK (United Kingdom)

Author keywords

Addition reactions; Cyclisations; Phosphorus; Radical reactions

Indexed keywords

AMINE; BISPYRROLIDINE DERIVATIVE; DIALLYAMINE DERIVATIVE; PHOSPHORUS; PHOSPHORUS HYDRIDE DERIVATIVE; PYRROLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; ESTERIFICATION;

EID: 51149094775 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2008-1072789 Document Type: Article

Times cited : (8)

References (43)

1
- 35349000182
- (a) Dochnahl, M.; Schulz, S. R.; Blechert, S. Synlett 2007, 2599.
- (2007) Synlett , pp. 2599
- Dochnahl, M.¹ Schulz, S.R.² Blechert, S.³

2
- 0021072992
- (b) Neukomm, G.; Roessler, F.; Johne, S.; Hesse, M. Planta Med. 1983, 48, 246.
- (1983) Planta Med , vol.48 , pp. 246
- Neukomm, G.¹ Roessler, F.² Johne, S.³ Hesse, M.⁴

3
- 0034051360
- Anderson, F. M.; O'Hare, C. C.; Hartley, J. A.; Robins, D. J. Anti-Cancer Drug Design 2000, 15, 119.
- (2000) Anti-Cancer Drug Design , vol.15 , pp. 119
- Anderson, F.M.¹ O'Hare, C.C.² Hartley, J.A.³ Robins, D.J.⁴

4
- 0024372756
- (a) Stout, D. M.; Black, L. A.; Barcelon-Yang, C.; Matier, W. L.; Brown, B. S.; Quon, C. Y.; Stampfli, H. F. J. Med. Chem. 1989, 32, 1910.
- (1989) J. Med. Chem , vol.32 , pp. 1910
- Stout, D.M.¹ Black, L.A.² Barcelon-Yang, C.³ Matier, W.L.⁴ Brown, B.S.⁵ Quon, C.Y.⁶ Stampfli, H.F.⁷

5
- 0021921508
- (b) Stout, D. M.; Matier, W. L.; Barcelon-Yang, C.; Reynolds, R. D.; Brown, B. S. J. Med. Chem. 1985, 28, 295.
- (1985) J. Med. Chem , vol.28 , pp. 295
- Stout, D.M.¹ Matier, W.L.² Barcelon-Yang, C.³ Reynolds, R.D.⁴ Brown, B.S.⁵

6
- 0028067715
- (a) Williams, M. A.; Rapoport, H. J. Org. Chem. 1994, 59, 3616.
- (1994) J. Org. Chem , vol.59 , pp. 3616
- Williams, M.A.¹ Rapoport, H.²

7
- 0000753661
- (b) Bernauer, K.; Gretillat, F. Helv. Chim. Acta 1989, 72, 477.
- (1989) Helv. Chim. Acta , vol.72 , pp. 477
- Bernauer, K.¹ Gretillat, F.²

8
- 33644532245
- (a) Denmark, S. E.; Fu, J.; Lawler, M. J. J. Org. Chem. 2006, 71, 1523.
- (2006) J. Org. Chem , vol.71 , pp. 1523
- Denmark, S.E.¹ Fu, J.² Lawler, M.J.³

9
- 0035955158
- (b) Denmark, S. E.; Fu, J. J. Am. Chem. Soc. 2001, 123, 9488.
- (2001) J. Am. Chem. Soc , vol.123 , pp. 9488
- Denmark, S.E.¹ Fu, J.²

10
- 9944231418
- (c) Periasamy, M.; Seenivasaperumal, M.; Dharma Rao, V. Tetrahedron: Asymmetry 2004, 15, 3847.
- (2004) Tetrahedron: Asymmetry , vol.15 , pp. 3847
- Periasamy, M.¹ Seenivasaperumal, M.² Dharma Rao, V.³

11
- 0025885921
- (d) Marshall, W. B.; Brewbaker, J. L.; Delaney, M. S. J. Appl. Polym. Sci. 1991, 42, 533.
- (1991) J. Appl. Polym. Sci , vol.42 , pp. 533
- Marshall, W.B.¹ Brewbaker, J.L.² Delaney, M.S.³

12
- 0034823456
- (e) Trost, B. M.; Ito, H.; Silcoff, E. R. J. Am. Chem. Soc. 2001, 123, 3367.
- (2001) J. Am. Chem. Soc , vol.123 , pp. 3367
- Trost, B.M.¹ Ito, H.² Silcoff, E.R.³

13
- 2542543701
- (f) Yang, D.; Chen, Y.-C.; Zhu, N.-Y. Org. Lett. 2004, 6, 1577.
- (2004) Org. Lett , vol.6 , pp. 1577
- Yang, D.¹ Chen, Y.-C.² Zhu, N.-Y.³

14
- 33645093416
- For recent work on addition reactions of phosphorus-centred radicals, see: a
- For recent work on addition reactions of phosphorus-centred radicals, see: (a) Jessop, C. M.; Parsons, A. F.; Routledge, A.; Irvine, D. J. Eur. J. Org. Chem. 2006, 1547.
- (2006) Eur. J. Org. Chem , pp. 1547
- Jessop, C.M.¹ Parsons, A.F.² Routledge, A.³ Irvine, D.J.⁴

15
- 0037433936
- (b) Jessop, C. M.; Parsons, A. F.; Routledge, A.; Irvine, D. Tetrahedron Lett. 2003, 44, 479.
- (2003) Tetrahedron Lett , vol.44 , pp. 479
- Jessop, C.M.¹ Parsons, A.F.² Routledge, A.³ Irvine, D.⁴

16
- 2942534474
- (c) Jessop, C. M.; Parsons, A. F.; Routledge, A.; Irvine, D. J. Tetrahedron Lett. 2004, 45, 5095.
- (2004) Tetrahedron Lett , vol.45 , pp. 5095
- Jessop, C.M.¹ Parsons, A.F.² Routledge, A.³ Irvine, D.J.⁴

17
- 11844280968
- (d) Cho, D. H.; Jang, D. O. Synlett 2005, 59.
- (2005) Synlett , pp. 59
- Cho, D.H.¹ Jang, D.O.²

18
- 33646241793
- (e) Hunt, T. A.; Parsons, A. F.; Pratt, R. J. Org. Chem. 2006, 71, 3656.
- (2006) J. Org. Chem , vol.71 , pp. 3656
- Hunt, T.A.¹ Parsons, A.F.² Pratt, R.³

19
- 17944370091
- (f) Montchamp, J.-L. J. Organomet. Chem. 2005, 690, 2388.
- (2005) J. Organomet. Chem , vol.690 , pp. 2388
- Montchamp, J.-L.¹

20
- 26844495597
- (g) Leca, D.; Fensterbank, L.; Lacôte, E.; Malacria, M. Chem. Soc. Rev. 2005, 34, 858.
- (2005) Chem. Soc. Rev , vol.34 , pp. 858
- Leca, D.¹ Fensterbank, L.² Lacôte, E.³ Malacria, M.⁴

21
- 28844444993
- (h) Parsons, A. F.; Sharpe, D. J.; Taylor, P. Synlett 2005, 2981.
- (2005) Synlett , pp. 2981
- Parsons, A.F.¹ Sharpe, D.J.² Taylor, P.³

22
- 28844438922
- (i) Hunt, T.; Parsons, A. F.; Pratt, R. Synlett 2005, 2978.
- (2005) Synlett , pp. 2978
- Hunt, T.¹ Parsons, A.F.² Pratt, R.³

23
- 17844371929
- (j) Healy, M. P.; Parsons, A. F.; Rawlinson, J. G. T. Org. Lett. 2005, 7, 1597.
- (2005) Org. Lett , vol.7 , pp. 1597
- Healy, M.P.¹ Parsons, A.F.² Rawlinson, J.G.T.³

24
- 33947603435
- (k) Carta, P.; Puljic, N.; Robert, C.; Dhimane, A.-L.; Fensterbank, L.; Lacôte, E.; Malacria, M. Org. Lett. 2007, 9, 1061.
- (2007) Org. Lett , vol.9 , pp. 1061
- Carta, P.¹ Puljic, N.² Robert, C.³ Dhimane, A.-L.⁴ Fensterbank, L.⁵ Lacôte, E.⁶ Malacria, M.⁷

25
- 51149121053
- (l) Montchamp, J.-L.; Antczak, M. I. Synthesis 2006, 3080.
- (2006) Synthesis , pp. 3080
- Montchamp, J.-L.¹ Antczak, M.I.²

26
- 39749186596
- (m) Healy, M. P.; Parsons, A. F.; Rawlinson, J. G. T. Synlett 2008, 329.
- (2008) Synlett , pp. 329
- Healy, M.P.¹ Parsons, A.F.² Rawlinson, J.G.T.³

27
- 24044552009
- (n) Beaufils, F.; Dénès, F.; Renaud, P. Angew. Chem. Int. Ed. 2005, 44, 5273.
- (2005) Angew. Chem. Int. Ed , vol.44 , pp. 5273
- Beaufils, F.¹ Dénès, F.² Renaud, P.³

28
- 51149117858
- All new compounds gave spectroscopic data and high-resolution mass spectrometric data consistent with their assigned structure
- All new compounds gave spectroscopic data and high-resolution mass spectrometric data consistent with their assigned structure.

29
- 51149105970
- Bis({4-methyl-1, 4-methylphenyl)sulfonyl]-3-pyrrolidinyl}methyl) phosphinic Acid (8a) A boiling solution of N,N-diallyl-4- methylbenzenesulfonamide (2a, 0.613 g, 2.439 mmol) and hypophosphorous acid (0.070 g, 1.061 mmol, in anhyd THF (5 mL) was treated with AIBN (4 x 0.087 g, 4 x 0.531 mmol) over 36 h. After cooling to r.t, brine (20 mL) was added and the mixture extracted with CH2Cl2 (3 x 20 mL, The combined layers were dried (MgSO4, concentrated (under reduced pressure, and column chromatography [SiO2, PE-EtOAc (4:6) to EtOAc-MeOH (1:1, gave phosphinic acid 8a (0.495 g, 82, as an inseparable mixture of isomers, with a cis/trans ratio of 2.2:1 (from the 1H NMR spectrum, white solid; mp 118-127°C. IR CH 2Cl2, νmax, 3541, 3058, 2964, 2882, 1598, 1479, 1454, 1406, 1384, 1337, 1160, 1093, 1044, 955 cm-1. cis-Diastereomers: 1
- 2: 567.1758; found: 567.1752.

30
- 0003106738
- (a) Williams, R. H.; Hamilton, L. A. J. Am. Chem. Soc. 1955, 77, 3411.
- (1955) J. Am. Chem. Soc , vol.77 , pp. 3411
- Williams, R.H.¹ Hamilton, L.A.²

31
- 0003100796
- (b) Nifant'ev, E. E.; Magdeeva, R. K.; Shchepet'eva, N. P. J. Gen. Chem. USSR 1980, 50, 1416.
- (1980) J. Gen. Chem. USSR , vol.50 , pp. 1416
- Nifant'ev, E.E.¹ Magdeeva, R.K.² Shchepet'eva, N.P.³

32
- 0000075077
- (c) Dubert, O.; Gautier, A.; Condamine, E.; Piettre, S. R. Org. Lett. 2002, 4, 359.
- (2002) Org. Lett , vol.4 , pp. 359
- Dubert, O.¹ Gautier, A.² Condamine, E.³ Piettre, S.R.⁴

33
- 0029098821
- Froestel, W.; Mickel, S. J.; Hall, R. G.; von Sprecher, G.; Strub, D.; Baumann, P. A.; Brugger, F.; Gentsch, C.; Jaekel, J.; Olpe, H.-R.; Rihs, G.; Vassout, A.; Waldmeier, P. C.; Bittiger, H. J. Med. Chem. 1995, 38, 3297.
- (1995) J. Med. Chem , vol.38 , pp. 3297
- Froestel, W.¹ Mickel, S.J.² Hall, R.G.³ von Sprecher, G.⁴ Strub, D.⁵ Baumann, P.A.⁶ Brugger, F.⁷ Gentsch, C.⁸ Jaekel, J.⁹ Olpe, H.-R.¹⁰ Rihs, G.¹¹ Vassout, A.¹² Waldmeier, P.C.¹³ Bittiger, H.¹⁴

34
- 51149105754
- 2 (4.3 equiv) in degassed dioxane for 3 d, followed by esterification, gave a 4.7:1 mixture of 9 and 10, respectively, in a combined yield of only 34%.
- 2 (4.3 equiv) in degassed dioxane for 3 d, followed by esterification, gave a 4.7:1 mixture of 9 and 10, respectively, in a combined yield of only 34%.

35
- 0036471109
- (a) Deprèle, S.; Montchamp, J.-L. J. Organomet. Chem. 2002, 643-644, 154.
- (2002) J. Organomet. Chem , vol.643-644 , pp. 154
- Deprèle, S.¹ Montchamp, J.-L.²

36
- 17944370091
- (b) Montchamp, J.-L. J. Organomet. Chem. 2005, 690, 2388.
- (2005) J. Organomet. Chem , vol.690 , pp. 2388
- Montchamp, J.-L.¹

37
- 0346159377
- (a) Cristau, H.-J.; Coulombeau, A.; Genevois-Borella, A.; Sanchez, F.; Pirat, J.-L. J. Organomet. Chem. 2002, 643-644, 381.
- (2002) J. Organomet. Chem , vol.643-644 , pp. 381
- Cristau, H.-J.¹ Coulombeau, A.² Genevois-Borella, A.³ Sanchez, F.⁴ Pirat, J.-L.⁵

38
- 0035812795
- (b) Deprèle, S.; Montchamp, J.-L. J. Org. Chem. 2001, 66, 6745.
- (2001) J. Org. Chem , vol.66 , pp. 6745
- Deprèle, S.¹ Montchamp, J.-L.²

39
- 84970626637
- (a) Gallagher, M. J.; Honegger, H. Aust. J. Chem. 1980, 33, 287.
- (1980) Aust. J. Chem , vol.33 , pp. 287
- Gallagher, M.J.¹ Honegger, H.²

40
- 0033555770
- (b) Kehler, J.; Ebert, B.; Dahl, O.; Krogsgaard-Larsen, P. Tetrahedron 1999, 55, 771.
- (1999) Tetrahedron , vol.55 , pp. 771
- Kehler, J.¹ Ebert, B.² Dahl, O.³ Krogsgaard-Larsen, P.⁴

41
- 51149085689
- -1, respectively. McGrady, J. E.; Pantazis, D. unpublished results.
- -1, respectively. McGrady, J. E.; Pantazis, D. unpublished results.

42
- 51149121499
- 0-(3, 4-Methyl-1, 4-methylphenyl)sulfonyl]-3-pyrrolidinyl}methyl, phenyl)phosphorothioyl]oxy}propyl){4-methyl-1, 4-methylphenyl)sulfonyl, 3-pyrrolidinyl}methyl(phenyl)phosphinothioate (16a) A boiling solution of N,N-diallyl-4-methylbenzene sulfonamide (2a, 0.372 g, 1.479 mmol) and O-(3, phenyl(thioxo)phosphoranyl]oxy}propyl)phenylphosphinothioate (14, 0.264 g, 0.741 mmol) in anhyd THF (15 mL) was treated portionwise with AIBN (4 x 0.024 g, 4 x 0.148 mmol) over 36 h. After cooling to r.t, 1 M aq NaOH (20 mL) was added and the mixture extracted with CH2Cl 2 (3 x 15 mL, The combined organic layers were dried (MgSO 4, concentrated (under reduced pressure, and column chromatography [SiO2, CH2Cl2-EtOAc (97:3, gave bispyrrolidine 16a (0.477 g, 75, as an inseparable mixture of isomers, with a cis/trans ratio of 2.5:1 from the 1H NMR spectrum, white solid
- 4: 859.2256; found: 859.2264.

43
- 4444312609
- Arndt, H.-D.; Welz, R.; Müller, S.; Ziemer, B.; Koert, U. Chem. Eur. J. 2004, 10, 3945.
- (2004) Chem. Eur. J , vol.10 , pp. 3945
- Arndt, H.-D.¹ Welz, R.² Müller, S.³ Ziemer, B.⁴ Koert, U.⁵

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.