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Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences

Volumn 69, Issue 5, 2014, Pages 554-566

A simple metal-free synthesis of 2,4,5-trisubstituted pyridines and pyridine N-oxides by [2+2] cycloaddition of enaminones to propyne iminium salts

(9) Bezenšek, Jure a Prek, Benjamin a,b Grošelj, Uroš a Golobič, Amalija a Stare, Katarina a Svete, Jurij a,b Kantlehner, Willi c Maas, Gerhard d Stanovnik, Branko a,b

a UNIVERSITY OF LJUBLJANA (Slovenia)

b Centre of Excellence (Slovenia)

c AALEN UNIVERSITY (Germany)

d UNIVERSITY OF ULM (Germany)

Author keywords

2,4,5 trisubstituted pyridine N oxides; 2,4,5 trisubstituted pyridines; Enaminones; Propyne iminium salts

Indexed keywords

DIMETHYLFORMAMIDE; KETONES; SALTS; SYNTHESIS (CHEMICAL);

ENAMINONES; IMINIUM SALTS; METHYL KETONES; N ,N-DIMETHYLFORMAMIDE DIMETHYL ACETAL; PROPYNES; PYRIDINE N-OXIDE; SIMPLE METALS; [2+2] CYCLOADDITION;

PYRIDINE;

EID: 84901724475 PISSN: 09320776 EISSN: None Source Type: Journal
DOI: 10.5560/ZNB.2014-4021 Document Type: Article

Times cited : (12)

References (60)

1
- 33745079610
- J. S. Carey, D. Laffan, C. Thomson, M. T. Williams, Org. Biomol. Chem. 2006, 4, 2337-2347.
- (2006) Org. Biomol. Chem. , vol.4 , pp. 2337-2347
- Carey, J.S.¹ Laffan, D.² Thomson, C.³ Williams, M.T.⁴

2
- 19944429281
- S. Marchaise-Oberwinkler, B. Nowicki, V. W. Pike, C. Halldin, J. Sandell, Y.-H. Chou, B. Gulyas, L. T. Brennum, L. Farde, H. V. Wikstroma, Bioorg. Med. Chem. 2005, 13, 883-893.
- (2005) Bioorg. Med. Chem. , vol.13 , pp. 883-893
- Marchaise-Oberwinkler, S.¹ Nowicki, B.² Pike, V.W.³ Halldin, C.⁴ Sandell, J.⁵ Chou, Y.-H.⁶ Gulyas, B.⁷ Brennum, L.T.⁸ Farde, L.⁹ Wikstroma, H.V.¹⁰

3
- 23644443066
- A. M. Lewis, M. Ough, M. M. Hinkhouse, M.-S. Tsao, L. W. Oberley, J. J. Cullen, Mol. Carcinog. 2005, 43, 215-224.
- (2005) Mol. Carcinog. , vol.43 , pp. 215-224
- Lewis, A.M.¹ Ough, M.² Hinkhouse, M.M.³ Tsao, M.-S.⁴ Oberley, L.W.⁵ Cullen, J.J.⁶

4
- 0036635291
- R. Capdeville, E. Buchdunger, J. Zimmermann, A. Matter, Nat. Rev. Drug. Discov. 2002, 1, 493-502.
- (2002) Nat. Rev. Drug. Discov. , vol.1 , pp. 493-502
- Capdeville, R.¹ Buchdunger, E.² Zimmermann, J.³ Matter, A.⁴

5
- 0242300219
- J. Quirk, M. Thornton, P. Kirkpatrick, Nat. Rev. Drug. Discov. 2003, 2, 769-770.
- (2003) Nat. Rev. Drug. Discov. , vol.2 , pp. 769-770
- Quirk, J.¹ Thornton, M.² Kirkpatrick, P.³

6
- 0025944918
- L. B. S. Kardono, C. K. Angerhofer, S. Tsauri, K. Padmawinata, J. M. Pezzuto, A. D. Kinghorn, J. Nat. Prod. 1991, 54, 1360-1367.
- (1991) J. Nat. Prod. , vol.54 , pp. 1360-1367
- Kardono, L.B.S.¹ Angerhofer, C.K.² Tsauri, S.³ Padmawinata, K.⁴ Pezzuto, J.M.⁵ Kinghorn, A.D.⁶

7
- 65249098984
- G. O'Donnell, R. Poeschl, O. Zimhony, M. Gunaratnam, J. B. C. Moreira, S. Neidle, D. Evangelopoulos, S. Bhakta, J. P. Malkinson, H. I. Boshoff, A. Lenaerts, S. Gibbons, J. Nat. Prod. 2009, 72, 360-365.
- (2009) J. Nat. Prod. , vol.72 , pp. 360-365
- O'Donnell, G.¹ Poeschl, R.² Zimhony, O.³ Gunaratnam, M.⁴ Moreira, J.B.C.⁵ Neidle, S.⁶ Evangelopoulos, D.⁷ Bhakta, S.⁸ Malkinson, J.P.⁹ Boshoff, H.I.¹⁰ Lenaerts, A.¹¹ Gibbons, S.¹²

8
- 33750435218
- J. Y. L. Chung, R. J. Cvetovich, M. McLaughlin, J. Amato, F.-R. Tsay, M. Jensen, S. Weissman, D. Zewge, J. Org. Chem. 2006, 71, 8602-8609.
- (2006) J. Org. Chem. , vol.71 , pp. 8602-8609
- Chung, J.Y.L.¹ Cvetovich, R.J.² McLaughlin, M.³ Amato, J.⁴ Tsay, F.-R.⁵ Jensen, M.⁶ Weissman, S.⁷ Zewge, D.⁸

9
- 0242269462
- For a review see: G. Chelucci, G. Orru, G. A. Pinna, Tetrahedron 2003, 59, 9471-9515.
- (2003) Tetrahedron , vol.59 , pp. 9471-9515
- Chelucci, G.¹ Orru, G.² Pinna, G.A.³

10
- 33846104288
- A. Malkov, P. Kocovsky, Eur. J. Org. Chem. 2007, 29-36.
- (2007) Eur. J. Org. Chem. , pp. 29-36
- Malkov, A.¹ Kocovsky, P.²

11
- 57149089914
- N. Takenaka, R. S. Sarangthem, B. Captain, Angew. Chem. Int. Ed. 2008, 47, 9708-9710.
- (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 9708-9710
- Takenaka, N.¹ Sarangthem, R.S.² Captain, B.³

12
- 85014580919
- J. Bosch, M.-L. Bennasar, Synlett 1995, 587-596.
- (1995) Synlett , pp. 587-596
- Bosch, J.¹ Bennasar, M.-L.²

13
- 33947629300
- A. Sinclair, R. A. Stockman, Nat. Prod. Rep. 2007, 24, 298-326.
- (2007) Nat. Prod. Rep. , vol.24 , pp. 298-326
- Sinclair, A.¹ Stockman, R.A.²

14
- 84906465557
- (Eds. A. R. Katritzky, C. A. Ramsden, E. F. V. Scriven, R. J. K. Taylor) Elsevier, Amsterdam
- P. A. Keller inComprehensive Heterocyclic Chemistry III, (Eds. A. R. Katritzky, C. A. Ramsden, E. F. V. Scriven, R. J. K. Taylor), Vol. 7, Elsevier, Amsterdam, 2008, pp. 217-307.
- (2008) Comprehensive Heterocyclic Chemistry III , vol.7 , pp. 217-307
- Keller, P.A.¹

15
- 21244490314
- (Ed.: D. StC. Black), Thieme Verlag, Stuttgart
- D. Spitzner in Science of Synthesis, Vol. 15, (Ed.: D. StC. Black), Thieme Verlag, Stuttgart, 2004, pp. 11-284.
- (2004) Science of Synthesis , vol.15 , pp. 11-284
- Spitzner, D.¹

16
- 84866025669
- (Ed.: D. StC. Black), Thieme Verlag, Stuttgart
- P. A. Keller inScience of Synthesis, Vol. 15, (Ed.: D. StC. Black), Thieme Verlag, Stuttgart, 2004, pp. 285-387.
- (2004) Science of Synthesis , vol.15 , pp. 285-387
- Keller, P.A.¹

17
- 0007360441
- G. Illuminati, F. Stegel, Adv. Heterocycl. Chem. 1983, 34, 305-444.
- (1983) Adv. Heterocycl. Chem. , vol.34 , pp. 305-444
- Illuminati, G.¹ Stegel, F.²

18
- 84901709348
- th ed., Blackwell Science Ltd., Oxford
- th ed., Blackwell Science Ltd., Oxford, 2000, p. 66.
- (2000) Heterocyclic Chemistry , pp. 66
- Joule, J.A.¹ Mills, K.²

19
- 84859574809
- J. A. Bull, J. J. Mousseau, G. Pelletier, A. B. Charette, Chem. Rev. 2012, 112, 2642-2713.
- (2012) Chem. Rev. , vol.112 , pp. 2642-2713
- Bull, J.A.¹ Mousseau, J.J.² Pelletier, G.³ Charette, A.B.⁴

20
- 0003660996
- Pergamon Press, New York
- J. J. Li, G. W. Gribble, Palladium in Heterocyclic Chemistry, Pergamon Press, New York 2000.
- (2000) Palladium in Heterocyclic Chemistry
- Li, J.J.¹ Gribble, G.W.²

21
- 33751424969
- G. Zeni, R. C. Larock, Chem. Rev. 2006, 106, 4644-4680.
- (2006) Chem. Rev. , vol.106 , pp. 4644-4680
- Zeni, G.¹ Larock, R.C.²

22
- 0003397781
- Wiley-VCH, New York
- F. Diederich, P. Stang (Eds.), Metal-Catalysed Cross-coupling Reactions; Wiley-VCH, New York 1998.
- (1998) Metal-Catalysed Cross-coupling Reactions
- Diederich, F.¹ Stang, P.²

23
- 78650300057
- C. Guetz, A. Luetzen, Synthesis 2010, 1, 85-93.
- (2010) Synthesis , vol.1 , pp. 85-93
- Guetz, C.¹ Luetzen, A.²

24
- 61449215236
- D. X. Yang, S. L. Colletti, K. Wu, M. Song, G. Y. Li, H. C. Shen, Org. Lett. 2009, 11, 381-384.
- (2009) Org. Lett. , vol.11 , pp. 381-384
- Yang, D.X.¹ Colletti, S.L.² Wu, K.³ Song, M.⁴ Li, G.Y.⁵ Shen, H.C.⁶

25
- 70149117010
- refs. cited therein
- D. M. Knapp, E. P. Gillis, M. D. Burke, J. Am. Chem. Soc. 2009, 131, 6961-6963, and refs. cited therein.
- (2009) J. Am. Chem. Soc. , vol.131 , pp. 6961-6963
- Knapp, D.M.¹ Gillis, E.P.² Burke, M.D.³

26
- 77949902067
- S.-H. Kim, R. D. Rieke, Tetrahedron 2010, 66, 3135-3146.
- (2010) Tetrahedron , vol.66 , pp. 3135-3146
- Kim, S.-H.¹ Rieke, R.D.²

27
- 77950371449
- S.-H. Kim, R. D. Rieke, Tetrahedron Lett. 2010, 51, 2657-2659.
- (2010) Tetrahedron Lett. , vol.51 , pp. 2657-2659
- Kim, S.-H.¹ Rieke, R.D.²

28
- 71049183112
- refs. cited therein
- B. M. Coleridge, C. S. Bello, D. H. Ellenberger, A. Leitner, Tetrahedron Lett. 2010, 51, 357-359, and refs. cited therein.
- (2010) Tetrahedron Lett. , vol.51 , pp. 357-359
- Coleridge, B.M.¹ Bello, C.S.² Ellenberger, D.H.³ Leitner, A.⁴

29
- 78650272462
- M. R. Luzung, J. S. Patel, J. Yin, J. Org. Chem. 2010, 75, 8330-8332.
- (2010) J. Org. Chem. , vol.75 , pp. 8330-8332
- Luzung, M.R.¹ Patel, J.S.² Yin, J.³

30
- 80955135889
- F. Zhang, X.-F. Duan, Org. Lett. 2011, 13, 6102-6105.
- (2011) Org. Lett. , vol.13 , pp. 6102-6105
- Zhang, F.¹ Duan, X.-F.²

31
- 84862907655
- J. Wen, R.-Y. Zhang, S.-Y. Chen, J. Zhang, X.-Q. Yu, J. Org. Chem. 2012, 77, 766-771.
- (2012) J. Org. Chem. , vol.77 , pp. 766-771
- Wen, J.¹ Zhang, R.-Y.² Chen, S.-Y.³ Zhang, J.⁴ Yu, X.-Q.⁵

32
- 80053126105
- C. Eidamshaus, H.-U. Reissig, Eur. J. Org. Chem. 2011, 30, 6056-6069.
- (2011) Eur. J. Org. Chem. , vol.30 , pp. 6056-6069
- Eidamshaus, C.¹ Reissig, H.-U.²

33
- 84888137980
- P. Hommes, S. Berlin, H.-U. Reissig, Synthesis 2013, 3288-3294.
- (2013) Synthesis , pp. 3288-3294
- Hommes, P.¹ Berlin, S.² Reissig, H.-U.³

34
- 0033367710
- B. Stanovnik, J. Heterocycl. Chem. 1999, 36, 1581-1593.
- (1999) J. Heterocycl. Chem. , vol.36 , pp. 1581-1593
- Stanovnik, B.¹

35
- 0033870638
- B. Stanovnik, J. Svete, Synlett 2000, 1077-1091.
- (2000) Synlett , pp. 1077-1091
- Stanovnik, B.¹ Svete, J.²

36
- 0001916519
- (Eds.: O. A. Attanasi, D. Spinelli), Società Chimica Italiana, Rome
- B. Stanovnik, J. Svete in Targets in Heterocyclic Systems. Chemistry and Properties, Vol. 4, (Eds.: O. A. Attanasi, D. Spinelli), Società Chimica Italiana, Rome 2000, p. 105.
- (2000) Targets in Heterocyclic Systems. Chemistry and Properties , vol.4 , pp. 105
- Stanovnik, B.¹ Svete, J.²

37
- 2942568249
- B. Stanovnik, J. Svete, Chem. Rev. 2004, 104, 2433-2480.
- (2004) Chem. Rev. , vol.104 , pp. 2433-2480
- Stanovnik, B.¹ Svete, J.²

38
- 17644419343
- J. Svete, J. Heterocycl. Chem. 2005, 42, 361-373.
- (2005) J. Heterocycl. Chem. , vol.42 , pp. 361-373
- Svete, J.¹

39
- 0033773802
- L. Selič, R. Jakše, K. Lampič, L. Golič, S. Golič-Grdadolnik, B. Stanovnik, Helv. Chim. Acta 2000, 83, 2802-2811.
- (2000) Helv. Chim. Acta , vol.83 , pp. 2802-2811
- Selič, L.¹ Jakše, R.² Lampič, K.³ Golič, L.⁴ Golič-Grdadolnik, S.⁵ Stanovnik, B.⁶

40
- 0035831974
- L. Selič, B. Stanovnik, Tetrahedron 2001, 57, 3159-3164.
- (2001) Tetrahedron , vol.57 , pp. 3159-3164
- Selič, L.¹ Stanovnik, B.²

41
- 2142815689
- R. Jakše, J. Svete, B. Stanovnik, A. Golobič, Tetrahedron 2004, 60, 4601-4608.
- (2004) Tetrahedron , vol.60 , pp. 4601-4608
- Jakše, R.¹ Svete, J.² Stanovnik, B.³ Golobič, A.⁴

42
- 21744448814
- Z. Časar, D. Bevk, J. Svete, B. Stanovnik, Tetrahedron 2005, 61, 7508-7519.
- (2005) Tetrahedron , vol.61 , pp. 7508-7519
- Časar, Z.¹ Bevk, D.² Svete, J.³ Stanovnik, B.⁴

43
- 33644696785
- J. Wagger, D. Bevk, A. Meden, J. Svete, B. Stanovnik, Helv. Chim. Acta 2006, 89, 240-248.
- (2006) Helv. Chim. Acta , vol.89 , pp. 240-248
- Wagger, J.¹ Bevk, D.² Meden, A.³ Svete, J.⁴ Stanovnik, B.⁵

44
- 33947191871
- J. Wagger, S. Golič-Grdadolnik, U. Grošelj, A. Meden, J. Svete, B. Stanovnik, Tetrahedron: Asymmetry 2007, 18, 464-475.
- (2007) Tetrahedron: Asymmetry , vol.18 , pp. 464-475
- Wagger, J.¹ Golič-Grdadolnik, S.² Grošelj, U.³ Meden, A.⁴ Svete, J.⁵ Stanovnik, B.⁶

45
- 39149087336
- J. Wagger, U. Grošelj, A. Meden, J. Svete, B. Stanovnik, Tetrahedron 2008, 64, 2801-2815.
- (2008) Tetrahedron , vol.64 , pp. 2801-2815
- Wagger, J.¹ Grošelj, U.² Meden, A.³ Svete, J.⁴ Stanovnik, B.⁵

46
- 79959939848
- J. Bezenšek, T. Koleša, U. Grošelj, A. Meden, K. Stare, J. Svete, B. Stanovnik, Curr. Org. Chem. 2011, 15, 2530-2539.
- (2011) Curr. Org. Chem. , vol.15 , pp. 2530-2539
- Bezenšek, J.¹ Koleša, T.² Grošelj, U.³ Meden, A.⁴ Stare, K.⁵ Svete, J.⁶ Stanovnik, B.⁷

47
- 77953122616
- J. Bezenšek, T. Koleša, U. Grošelj, J. Wagger, K. Stare, A. Meden, J. Svete, B. Stanovnik, Tetrahedron Lett. 2010, 51, 3392-3397.
- (2010) Tetrahedron Lett. , vol.51 , pp. 3392-3397
- Bezenšek, J.¹ Koleša, T.² Grošelj, U.³ Wagger, J.⁴ Stare, K.⁵ Meden, A.⁶ Svete, J.⁷ Stanovnik, B.⁸

48
- 84981754261
- F. Bohlmann, D. Rahtz, Chem. Ber. 1957, 90, 2265-2272.
- (1957) Chem. Ber. , vol.90 , pp. 2265-2272
- Bohlmann, F.¹ Rahtz, D.²

49
- 0034940011
- M. C. Bagley, J. W. Dale, J. Bower, Synlett 2001, 1149-1151.
- (2001) Synlett , pp. 1149-1151
- Bagley, M.C.¹ Dale, J.W.² Bower, J.³

50
- 84861222638
- J. Bezenšek, B. Prek, U. Grošelj, M. Kasunič, J. Svete, B. Stanovnik, Tetrahedron 2012, 68, 4719-4731.
- (2012) Tetrahedron , vol.68 , pp. 4719-4731
- Bezenšek, J.¹ Prek, B.² Grošelj, U.³ Kasunič, M.⁴ Svete, J.⁵ Stanovnik, B.⁶

51
- 0000578581
- G. Maas, B. Singer, P. Wald, M. Gimmy, Chem. Ber. 1988, 121, 1847-1854.
- (1988) Chem. Ber. , vol.121 , pp. 1847-1854
- Maas, G.¹ Singer, B.² Wald, P.³ Gimmy, M.⁴

52
- 0000972604
- R. Rahm, G. Maas, Chem. Ber. 1994, 127, 1295-1303.
- (1994) Chem. Ber. , vol.127 , pp. 1295-1303
- Rahm, R.¹ Maas, G.²

53
- 84861642810
- K. Drandarov, I. Tiritiris, O. Wassiljew, H.-U. Siehl, W. Kantlehner, Chem. Eur. J. 2011, 18, 7224-7228.
- (2011) Chem. Eur. J. , vol.18 , pp. 7224-7228
- Drandarov, K.¹ Tiritiris, I.² Wassiljew, O.³ Siehl, H.-U.⁴ Kantlehner, W.⁵

54
- 73849131566
- COLLECT Nonius BV, Delft (The Netherlands)
- R. Hooft, COLLECT, Nonius KappaCCD Data Collection Software, Nonius BV, Delft (The Netherlands) 1998.
- (1998) Nonius KappaCCD Data Collection Software
- Hooft, R.¹

55
- 0031059866
- (Eds.: C. W. Carter Jr, R. M. Sweet), Academic Press, New York
- Z. Otwinowski, W. Minor in Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A (Eds.: C. W. Carter Jr, R. M. Sweet), Academic Press, New York, 1997, pp. 307-326.
- (1997) Methods in Enzymology, Vol. 276, Macromolecular Crystallography , Issue.PART A , pp. 307-326
- Otwinowski, Z.¹ Minor, W.²

56
- 84856951343
- (version 1.171.35.11). Agilent Technologies, Yarnton, Oxfordshire (England)
- CRYSALIS PRO (version 1.171.35.11). Agilent Technologies, Yarnton, Oxfordshire (England) 2011.
- (2011) Crysalis Pro

57
- 0242560405
- A. Altomare, M. C. Burla, M. Camalli, G. L. Cascarano, C. Giacovazzo, A. Guagliardi, A. G. G. Moliterni, G. Polidori, R. Spagna, J. Appl. Crystallogr. 1999, 32, 115-119.
- (1999) J. Appl. Crystallogr. , vol.32 , pp. 115-119
- Altomare, A.¹ Burla, M.C.² Camalli, M.³ Cascarano, G.L.⁴ Giacovazzo, C.⁵ Guagliardi, A.⁶ Moliterni, A.G.G.⁷ Polidori, G.⁸ Spagna, R.⁹

58
- 37549039510
- G. M. Sheldrick, Acta Crystallogr. 2008, A64, 112-122.
- (2008) Acta Crystallogr. , vol.A64 , pp. 112-122
- Sheldrick, G.M.¹

59
- 0004271269
- (version 1.0.2), Oak Ridge Thermal Ellipsoid Plot Program for Crystal Structure Illustrations, Rep. ORNL-6895, Oak Ridge National Laboratory, Oak Ridge, TN (USA)
- C. K. Johnson, M. N. Burnett, ORTEP-III (version 1.0.2), Oak Ridge Thermal Ellipsoid Plot Program for Crystal Structure Illustrations, Rep. ORNL-6895, Oak Ridge National Laboratory, Oak Ridge, TN (USA) 1996.
- (1996) ORTEP-III
- Johnson, C.K.¹ Burnett, M.N.²

60
- 33646767009
- L. J. Farrugia, J. Appl. Crystallogr. 1997, 30, 565.
- (1997) J. Appl. Crystallogr. , vol.30 , pp. 565
- Farrugia, L.J.¹

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