Application of 3-bromo-3-ethylazetidines and 3-ethylideneazetidines for the synthesis of functionalized azetidines

Synlett

Volumn 25, Issue 1, 2014, Pages 75-80

  Stanković, Sonja ^a   D'Hooghe, Matthias ^a   Vanderhaegen, Tim ^a   Abbaspour Tehrani, Kourosch ^a,b   De Kimpe, Norbert ^a  

^a GHENT UNIVERSITY   (Belgium)

^b UNIVERSITY OF ANTWERP   (Belgium)

Author keywords

heterocycles; nitrogen; nucleophiles; rearrangement; ring opening; spiro compounds

Indexed keywords

1 ARYLMETHYL 3 ETHYLIDENEAZETIDINE DERIVATIVE; 1 TERT BUTYL 3 ETHYLIDENEAZETIDINE; 2 ALKYLIDENEAZETIDINE DERIVATIVE; 2 BROMOMETHYL 2ETHYLAZIRIDINE DERIVATIVE; 2 ETHYLPROPENAL; 3 ALKYLIDENEAZETIDINE DERIVATIVE; 3 BROMO 1 TERT BUTYLAZETIDINE; 3 BROMO 3 ETHYLAZETIDINE DERIVATIVE; 3 BROMO 3 METHYLAZETIDINE DERIVATIVE; 3 ETHYLIDENEAZETIDINE DERIVATIVE; ALLYLAMINE DERIVATIVE; AZETIDINE; AZETIDINE DERIVATIVE; CARBON; NITROGEN; NUCLEOPHILE; OXYGEN; UNCLASSIFIED DRUG;

ARTICLE; BROMINATION; CHEMICAL BOND; CHEMICAL COMPOSITION; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; COMPARATIVE STUDY; ROOM TEMPERATURE; SUBSTITUTION REACTION; SYNTHESIS;

EID: 84890554615     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0033-1340250     Document Type: Article

References (75)

1. Tanner D. Angew. Chem., Int. Ed. Engl. 1994; 33: 599
2. Osborn HM. I, Sweeney J. Tetrahedron: Asymmetry 1997; 8: 1693
3. Sweeney JB. Chem. Soc. Rev. 2002; 31: 247
4. Singh GS, D’hooghe M, De Kimpe N. Chem. Rev. 2007; 107: 2080
5. Stanković S, D’hooghe M, Catak S, Eum H, Waroquier M, Van Speybroeck V, De Kimpe N, Ha H.-J. Chem. Soc. Rev. 2012; 41: 643
6. Couty F In Science of Synthesis . Vol. 40a. Enders D. Georg Thieme Verlag; Stuttgart: 2009: 773-817
7. Couty F, Durrat F, Evano G. Targets Heterocycl. Syst. 2005; 9: 186
8. Yadav LD. S, Srivastava VP, Patel R. Tetrahedron Lett. 2008; 49: 5652
9. Van Brabandt W, Mangelinckx S, D’hooghe M, Van Driessche B, De Kimpe N. Curr. Org. Chem. 2009; 13: 829
10. Brandi A, Cicchi S, Cordero FM. Chem. Rev. 2008; 108: 3988
11. Bott MT, West FG. Heterocycles 2012; 84: 223
12. Couty F, Drouillat B, Evano G, David O. Eur. J. Org. Chem. 2013; 2045
13. Mangelinckx S, Žukauskaitė A, Buinauskaitė V, Šačkus A, De Kimpe N. Tetrahedron Lett. 2008; 49: 6896
14. Žukauskaitė A, Mangelinckx S, Buinauskaitė V, Šačkus A, De Kimpe N. Amino Acids 2011; 41: 541
15. Cromwell NH, Phillips B. Chem. Rev. 1979; 79: 331
16. Moore JA, Ayers RS. Chemistry of Heterocyclic Compounds-Small Ring Heterocycles. Hassner A. Wiley; New York: 1983. Part 2 1-217
17. Davies DE, Storr RC. Comprehensive Heterocyclic Chemistry . Vol. 7, Part 5. Lwowski W. Pergamon; Oxford: 1984: 237-284
18. De Kimpe N. Three- and Four-Membered Rings, With All Fused Systems Containing Three- and Four-Membered Rings. In Comprehensive Heterocyclic Chemistry II . Vol. 1. Padwa A. Chap. 1.21 Elsevier; Oxford: 1996
19. Ojima I, Zhao M, Yamato T, Nakahashi K. J. Org. Chem. 1991; 56: 5263
20. Van Brabandt W, Dejaegher Y, Van Landeghem R, De Kimpe N. Org. Lett. 2006; 8: 1101
21. Van Brabandt W, Van Landeghem R, De Kimpe N. Org. Lett. 2006; 8: 1105
22. Sulmon P, De Kimpe N, Schamp N. J. Chem. Soc., Chem. Commun. 1985; 715
23. Sulmon P, De Kimpe N, Schamp N, Tinant B, Declercq J.-P. Tetrahedron 1988; 44: 3653
24. Aelterman W, De Kimpe N, Declercq J.-P. J. Org. Chem. 1998; 63: 6
25. Dejaegher Y, Mangelinckx S, De Kimpe N. J. Org. Chem. 2002; 67: 2075
26. Colpaert F, Mangelinckx S, De Brabandere S, De Kimpe N. J. Org. Chem. 2011; 76: 2204
27. Colpaert F, Mangelinckx S, De Kimpe N. Org. Lett. 2010; 12: 1904
28. Marehand AP, Ramanaiah KC. V, Bott SG, Gilbert JC, Kirschner S. Tetrahedron Lett. 1996; 37: 8101
29. Collier PN. Tetrahedron Lett. 2009; 50: 3909
30. Hanessian S, Fu J.-M, Chiara J.-L, Di Fabio R. Tetrahedron Lett. 1993; 34: 4157
31. Marehand AP, Devasagayaraj A. J. Org. Chem. 1997; 62: 4434
32. Burtoloso AC. B, Correia CR. D. Tetrahedron 2008; 64: 9928
33. Hanessian S, Fu J.-M, Tu Y. Tetrahedron Lett. 1993; 34: 4153
34. Emmer G. Tetrahedron 1992; 48: 7165
35. Liang Y, Raju R, Le T, Taylor CD, Howell AR. Tetrahedron Lett. 2009; 50: 1020
36. Stanković S, D’hooghe M, Abbaspour Tehrani K, De Kimpe N. Tetrahedron Lett. 2012; 53: 107
37. Van Driessche B, Van Brabandt W, D’hooghe M, Dejaegher Y, De Kimpe N. Tetrahedron 2006; 62: 6882
38. Abbaspour Tehrani K, De Kimpe N. Curr. Org. Chem. 2009; 13: 854
39. Mangelinckx S, Boeykens M, De Kimpe N. Synlett 2008; 1394
40. Lu H, Li C. Org. Lett. 2006; 8: 5365
41. Sulmon P, De Kimpe N, Schamp N. J. Org. Chem. 1988; 53: 4462
42. De Kimpe N, Boeykens M. J. Org. Chem. 1994; 59: 5189
43. De Kimpe N, Boeykens M. J. Org. Chem. 1994; 59: 5189
44. Abbaspour Tehrani K, De Kimpe N. Tetrahedron Lett. 2000; 41: 1975
45. Cainelli G, Giacomini D, Gazzano M, Galletti P, Quintavalla A. Tetrahedron Lett. 2008; 49: 5652
46. Stanković S, Goossens H, Catak S, Tezcan M, Waroquier M, Van Speybroeck V, D’hooghe M, De Kimpe N. J. Org. Chem. 2012; 77: 3181
47. Stanković S, Catak S, D’hooghe M, Goossens H, Abbaspour Tehrani K, Bogaert P, Waroquier M, Van Speybroeck V, De Kimpe N. J. Org. Chem. 2011; 76: 2157
48. Ma S, Yoon DH, Ha H.-J, Lee WK. Tetrahedron Lett. 2007; 48: 269
49. Fujiwara M, Baba A, Matsuda H. J. Heterocycl. Chem. 1989; 26: 1659
50. Shibata I, Nakamura K, Baba A, Matsuda H. Bull. Chem. Soc. Jpn. 1989; 62: 853
51. Baba A, Shibata I, Fujiwara M, Matsuda H. Tetrahedron Lett. 1985; 26: 5167
52. Rice GT, White MC. J. Am. Chem. Soc. 2009; 131: 11707
53. Nahra F, Liron F, Prestat G, Mealli C, Messaoudi A, Poli G. Chem. Eur. J. 2009; 15: 11078
54. Mangelinckx S, Nural Y, Dondas HA, Denolf B, Sillanpää R, De Kimpe N. Tetrahedron 2010; 66: 4115
55. Davies SG, Garner AC, Robert PM, Smith AD, Sweet MJ, Thomson JE. Org. Biomol. Chem. 2006; 4: 2753
56. Park M, Lee J. Arch. Pharmacol. Res. 1993; 16: 158
57. Li X, Wang R, Wang Y, Chen H, Li Z, Ba C, Zhang J. Tetrahedron 2008; 64: 9911
58. McElroy CR, Aricò F, Benetollo F, Tundo P. Pure Appl. Chem. 2012; 84: 707
59. Wang G, Ella-Menye J.-R, Sharma V. Bioorg. Med. Chem. Lett. 2006; 16: 2177
60. Podgoršek A, Iskra J. Molecules 2010; 15: 2857
61. Guérot C, Tchitchanov BH, Knust H, Carreira EM. Org. Lett. 2011; 13: 780
62. Marehand AP, Devasagayaraj A. Heterocycles 1998; 49: 149
63. Lamb P. PCT Int. Appl 2008076415, 2008
64. Aay N, Anand NK, Bowles OJ, Bussenius J, Costanzo S, Curtis JK, Dubenko L, Joshi AA, Kennedy AR, Kim AI, Koltun E, Manalo J.-CL, Peto CJ, Rice KD, Tsang TH. PCT Int. Appl 2007044515, 2007
65. Burkhard JA, Guérot C, Knust H, Rogers-Evans M, Carreira EM. Org. Lett. 2010; 12: 1944
66. Meyers MJ, Muizebelt I, van Wiltenburg J, Brown DL, Thorarensen A. Org. Lett. 2009; 11: 3523
67. Burkhard JA, Guérot C, Knust H, Carreira EM. Org. Lett. 2012; 14: 66
68. Li DB, Rogers-Evans M, Carreira EM. Org. Lett. 2011; 13: 6134
69. Žukauskaitė A, Mangelinckx S, Callebaut G, Wybon C, Šačkus A, De Kimpe N. Tetrahedron 2013; 69: 3437
70. Thakur VV, Sudalai A. Tetrahedron Lett. 2003; 44: 989
71. Sureshkumar D, Maity S, Chandrasekaran S. J. Org. Chem. 2006; 71: 1653
72. Alcaide B, Almendros P, Aragoncillo C, Cabrero G, Callejo R, Ruiz MP. Eur. J. Org. Chem. 2008; 4434
73. Simone MI, Edwards AA, Tranter GE, Fleet GW. J. Tetrahedron: Asymmetry 2008; 19: 2887
74. Chincholkar PM, Kale AS, Gumaste VK, Rakeeb A, Deshmukh AS. Tetrahedron 2009; 65: 2605
75. Grochowskit E, Gluziliski P, Krajewski JW, Pupek K. J. Mol. Struct. 1992; 269: 141