Deployment of Small-Ring Azaheterocycles as Building Blocks for the Synthesis of Organofluorine Compounds

Synlett

Volumn 27, Issue 10, 2016, Pages 1486-1510

  Dolfen, Jeroen ^a   De Kimpe, Norbert ^a   D'Hooghe, Matthias ^a  

^a GHENT UNIVERSITY   (Belgium)

Author keywords

azetidines; aziridines; fluorine; ring opening; lactams

Indexed keywords

1 ALKYL 2 [TRIFLUOROMETHYL]AZIRIDINE DERIVATIVE; 1 BENZYL 2 PHENYL 2 [TRIFLUOROMETHYL]AZIRIDINE; 1 TOSYL 2 [TRIFLUOROMETHYL]AZIRIDINE; 1 TOSYL 3 [TRIFLUOROMETHYL]AZIRIDINE; 2 FLUOROAZIRIDINE DERIVATIVE; 2 [FLUOROMETHYL]AZIRIDINE; 2 [TRIFLUOROMETHYL]AZEPANE DERIVATIVE; 2 [TRIFLUOROMETHYL]AZETIDINE 3 OL; 2 [TRIFLUOROMETHYL]AZETIDINE DERIVATIVE; 2 [TRIFLUOROMETHYL]AZIRIDINE DERIVATIVE; 2 [TRIFLUOROMETHYL]OXIRANE; 2 [TRIFLUOROMETHYL]PIPERIDINE DERIVATIVE; 2 [TRIFLUOROMETHYL]PYRROLIDINE DERIVATIVE; 3 AMINO 4,4,4 TRIFLUOROBUTYRIC ACID; 3 ARYL 2 FLUOROAZIRIDINE DERIVA TIVE; 3 FLUORO 3 METHYLAZETIDINE; 3 FLUOROAZETIDINE; 3 NONSUBSTITUTED 2 MONOFLUOROAZIRIDINE DERIVATIVE; AZETIDINE; AZETIDINE DERIVATIVE; AZIRIDINE DERIVATIVE; CIS 1 ALKYL 2 [ METHYL] 3 [TRIFLUOROMETHYL]AZIRIDINE DERIVATIVE; ETHYL 1 TOSYL 2 [TRIFLUOROMETHYL]AZIRIDINE 2 CARBOXYLATE; ORGANOFLUORINE DERIVATIVE; PHENETHYLAMINE DERIVATIVE; TRANS 1 ALKYL 2 [PHENYL] 3 [TRIFLUOROMETHYL]AZIRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ALLYLATION; ARTICLE; BROMINATION; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; COLUMN CHROMATOGRAPHY; CYCLIZATION; DEBENZYLATION; DISTILLATION; HYDROLYSIS; ISOMERIZATION; NUCLEOPHILICITY; POLYMERIZATION; PROTON TRANSPORT; PURIFICATION; REACTION TIME; RING CLOSING METATHESIS; RING OPENING; STEREOCHEMISTRY; SYNTHESIS; THERMODYNAMICS;

EID: 84961226854     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0035-1561379     Document Type: Article

References (123)

1. Bégué J.-P, Bonnet-Delpon D. J. Fluorine Chem.: 2006; 127 992
2. Bégué J.-P, Bonnet-Delpon D. Bioorganic and Medicinal Chemistry of Fluorine. Wiley Hoboken, NJ: 2007; 1 365
3. Bohm H. J., Banner D., Bendels S., Kansy M., Kuhn B., Muller K., Obst-Sander U., Stahl M. ChemBioChem: 2004; 5 637
4. Gillis E. P., Eastman K. J., Hill M. D., Donnelly D. J., Meanwell N. A. J. Med. Chem.: 2015; 58 8315
5. Meanwell N. A., Eastman K. J., Gillis E. P. Tactical Applications of Fluorine in Drug Design and Development In Fluorine in Heterocyclic Chemistry. Nenajdenko V. Springer International Cham, Switzerland: 2014; 1 54
6. Hagmann W. K. J. Med. Chem.: 2008; 51 4359
7. Isanbor C., O'Hagan D. J. Fluorine Chem.: 2006; 127 303
8. Kirk K. L. J. Fluorine Chem.: 2006; 127 1013
9. Muller K., Faeh C., Diederich F. Science: 2007; 317 1881
10. Purser S., Moore P. R., Swallow S., Gouverneur V. Chem. Soc. Rev.: 2008; 37 320
11. Shah P., Westwell A. D. J. Enzyme Inhib. Med. Chem.: 2007; 22
12. Wang J., Sanchez-Rosello M., Acena J. L., del Pozo C., Sorochinsky A. E., Fustero S., Soloshonok V. A., Liu H. Chem. Rev.: 2014; 114 2432
13. Yamazaki T., Taguchi T., Ojima I. Unique Properties of Fluorine and Their Relevance to Medicinal Chemistry and Chemical Biology In Fluorine in Heterocyclic Chemistry Volume 1: 5-Membered Heterocycles and Macrocycles. Ojima I. Wiley-Blackwell Chichester, UK: 2009; 1 46
14. Champagne P. A., Desroches J., Hamel J. D., Vandamme M., Paquin J. F. Chem. Rev.: 2015; 115 9073
15. Liang T., Neumann C. N., Ritter T. Angew. Chem. Int. Ed.: 2013; 52 8214
16. Neumann C. N., Ritter T. Angew. Chem. Int. Ed.: 2015; 54 3216
17. Besset T., Poisson T., Pannecoucke X. Chem. Eur. J.: 2014; 20 16830
18. Yang X., Wu T., Phipps R. J., Toste F. D. Chem. Rev.: 2015; 115 826
19. O'Hagan D. Chem. Soc. Rev.: 2008; 37 308
20. Smart B. E. J. Fluorine Chem.: 2001; 109 3
21. Morgenthaler M., Schweizer E., Hoffmann-Röder A., Benini F., Martin R. E., Jaeschke G., Wagner B., Fischer H., Bendels S., Zimmerli D. ChemMedChem: 2007; 2 1100
22. van Niel M. B., Colins I., Beer M. S., Broughton H. B., Cheng S. K. F, Goodacre S. C., Heald A., Locker K. L., Macleod A. M., Morrison D., Moyes C. R., Connor D. O., Pike A., Rowley M., Russell M. G. N, Sohal B., Stanton J. A., Thomas S., Verrier H., Watt A. P., Castro J. L. J. Med. Chem.: 1999; 42 2087
23. Callebaut G., Meiresonne T., De Kimpe N., Mangelinckx S. Chem. Rev.: 2014; 114 7954
24. Pearson W. H., Lian B. W., Bergmeier S. C. In Comprehensive Heterocyclic Chemistry II. Vol. 1 Padwa A Pergamon: Oxford: 1996; 1 60
25. Singh G., D'hooghe M., De Kimpe N. Azetidines, Azetines, and Azetes: Monocyclic In Comprehensive Heterocyclic Chemistry III. Vol. 2 Stevens C. V. Elsevier Oxford: 2008; 1
26. Singh G. S., D'hooghe M., De Kimpe N. Chem. Rev.: 2007; 107 2080
27. Stankovic 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
28. Hirotaki K., Takehiro Y., Kamaishi R., Yamada Y., Hanamoto T. Chem. Commun.: 2013; 49 7965
29. Konev A. S., Abbaspour Tehrani K., Khlebnikov A. F., Novikov M. S., Magull J. Russ. J. Org. Chem.: 2010; 46 976
30. Konev A. S., Novikov M. S., Khlebnikov A. F. Tetrahedron Lett.: 2005; 46 8337
31. Konev A. S., Novikov M. S., Khlebnikov A. F. Russ. J. Org. Chem.: 2007; 43 286
32. Khlebnikov A. F., Novikov M. S., Shinkevich E. Y., Vidovic D. Org. Biomol. Chem.: 2005; 3 4040
33. Usuki Y., Fukuda Y., Iio H. ITE Lett. Batteries New Technol. Med.: 2001; 2 237
34. Seyferth D., Woodruff R. A. J. Org. Chem.: 1973; 38 4031
35. Yamanaka H., Kikui J., Teramura K., Ando T. J. Org. Chem.: 1976; 41 3794
36. Van Hende E., Verniest G., Surmont R., De Kimpe N. Org. Lett.: 2007; 9 2935
37. Verniest G., Colpaert F., Van Hende E., De Kimpe N. J. Org. Chem.: 2007; 72 8569
38. Carpenter W., Haymaker A., Moore D. W. J. Org. Chem.: 1966; 31 789
39. Krespan C. G. J. Org. Chem.: 1986; 51 332
40. Logothetis A. J. Org. Chem.: 1964; 29 3049
41. Lork A., Gard G., Hare M., Mews R., Stohrer W.-D, Winter R. J. Chem. Soc., Chem. Commun.: 1992; 12 898
42. Petrov V. A. J. Fluorine Chem.: 2000; 106 25
43. Zeifman Y. V., Ter-Gabrielyan E., Gambaryan N. P., Knunyants I. L. Russ. Chem. Rev.: 1984; 53 256
44. D'hooghe M., Catak S., Stanković S., Waroquier M., Kim Y., Ha H. J., Van Speybroeck V., De Kimpe N. Eur. J. Org. Chem.: 2010; 2010, 4920
45. Akiyama T., Ogi S., Fuchibe K. Tetrahedron Lett.: 2003; 44 4011
46. Colantoni D., Fioravanti S., Pellacani L., Tardella P. A. Org. Lett.: 2004; 6 197
47. Crousse B., Narizuka S., Bonnet-Delpon D., Bégué J.-P. Synlett: 2001; 679
48. Davoli P., Forni A., Franciosi C., Moretti I., Prati F. Tetrahedron: Asymmetry: 1999; 10 2361
49. Fioravanti S., Colantoni D., Pellacani L., Tardella P. A. J. Org. Chem.: 2005; 70 3296
50. Grellepois F., Nonnenmacher J., Lachaud F., Portella C. Org. Biomol. Chem.: 2011; 9 1160
51. Higashiyama K., Matsumura M., Shiogama A., Yamauchi T., Ohmiya S. Heterocycles: 2002; 58 431
52. Karimova N. M., Teplenicheva Y. L., Kolomiets A. F., Fokin A. V. Russ. Chem. Bull.: 1997; 46 1136
53. Katagiri T., Ihara H., Takahashi M., Kashino S., Furuhashi K., Uneyama K. Tetrahedron: Asymmetry: 1997; 8 2933
54. Katagiri T., Katayama Y., Taeda M., Ohshima T., Iguchi N., Uneyama K. J. Org. Chem.: 2011; 76 9305
55. Katagiri T., Takahashi M., Fujiwara Y., Ihara H., Uneyama K. J. Org. Chem.: 1999; 64 7323
56. Maeda R., Ishibashi R., Kamaishi R., Hirotaki K., Furuno H., Hanamoto T. Org. Lett.: 2011; 13 6240
57. Maeda R., Ooyama K., Anno R., Shiosaki M., Azema T., Hanamoto T. Org. Lett.: 2010; 12 2548
58. Rinaudo G., Narizuka S., Askari N., Crousse B., Bonnet-Delpon D. Tetrahedron Lett.: 2006; 47 2065
59. Tanaka K., Ohsuga M., Sugimoto Y., Okafuji Y., Mitsuhashi K. J. Fluorine Chem.: 1988; 39 39
60. Yamauchi Y., Kawate T., Itahashi H., Katagiri T., Uneyama K. Tetrahedron Lett.: 2003; 44 6319
61. Yamauchi Y., Kawate T., Katagiri T., Uneyama K. Tetrahedron: 2003; 59 9839
62. Yoshiki M., Ishibashi R., Yamada Y., Hanamoto T. Org. Lett.: 2014; 16 5509
63. Barata-Vallejo S., Lantano B., Postigo A. Chem. Eur. J.: 2014; 20 16806
64. Charpentier J., Früh N., Togni A. Chem. Rev.: 2014; 115 650
65. Lin P., Jiang J. Tetrahedron: 2000; 56 3635
66. Ma J. A., Cahard D. Chem. Rev.: 2004; 104 6119
67. Prakash G. S., Mandal M. J. Fluorine Chem.: 2001; 112 123
68. Rubiales G., Alonso C., de Marigorta E. M., Palacios F. ARKIVOC: 2014; (ii) 362
69. Shao X., Xu C., Lu L., Shen Q. Acc. Chem. Res: 2015; 48 1227
70. Shibata N., Matsnev A., Cahard D. Beilstein J. Org. Chem.: 2010; 6 65
71. Singh R. P., Shreeve J. M. Tetrahedron: 2000; 56 7613
72. Wang S.-M, Han J.-B, Zhang C.-P, Qin H.-L, Xiao J.-C. Tetrahedron: 2015; 71 7949
73. Wei Z. Chin. J. Appl. Chem.: 2014; 31 627
74. Zhang C. Adv. Synth. Catal.: 2014; 356 2895
75. Zhang C. Org. Biomol. Chem.: 2014; 12 6580
76. Zhu W., Wang J., Wang S., Gu Z., Aceña J. L., Izawa K., Liu H., Soloshonok V. A. J. Fluorine Chem.: 2014; 167 37
77. Künzi S. A., Morandi B., Carreira E. M. Org. Lett.: 2012; 14 1900
78. Chai Z., Bouillon J.-P, Cahard D. Chem. Commun.: 2012; 48 9471
79. Félix C. P., Khatimi N., Laurent A. J. Tetrahedron Lett.: 1994; 35 3303
80. Kenis S., D'hooghe M., Verniest G., Nguyen V. D., Thi T. A., Van Nguyen T., De Kimpe N. Org. Biomol. Chem.: 2011; 9 7217
81. De Kimpe N., Schamp N. Org. Prep. Proced. Int.: 1979; 11 115
82. De Kimpe N., Sulmon P., Brunet P. J. Org. Chem.: 1990; 55 5777
83. De Kimpe N., Verhé R., De Buyck L., Hasma H., Schamp N. Tetrahedron: 1976; 32 2457
84. De Kimpe N., Verhé R., De Buyck L., Schamp N. Synth. Commun.: 1975; 5 269
85. Obijalska E., Mlostoń G., Linden A., Heimgartner H. Helv. Chim. Acta: 2010; 93 1725
86. Testa L., Akssira M., Zaballos-Garcla E., Arroyo P., Domingo L. R., Sepúlveda-Arques J. Tetrahedron: 2003; 59 677
87. Moens M., De Kimpe N., D'hooghe M. J. Org. Chem.: 2014; 79 5558
88. De Kimpe N., Verhe R., De Buyck L., Schamp N. J. Org. Chem.: 1980; 45 5319
89. Dolfen J., Kenis S., Van Hecke K., De Kimpe N., D'hooghe M. Chem. Eur. J.: 2014; 20 10650
90. Kenis S., D'hooghe M., Verniest G., Reybroeck M., Dang Thi T. A., Pham The C., Thi Pham T., Törnroos K. W., Van Nguyen T., De Kimpe N. Chem. Eur. J.: 2013; 19 5966
91. Huang C. Y., Doyle A. G. Chem. Rev.: 2014; 114 8153
92. Ohno H. Chem. Rev.: 2014; 114 7784
93. Padwa A., Murphree S. S. ARKIVOC: 2006; (iii) 6
94. Sweeney J. B. Chem. Soc. Rev.: 2002; 31 247
95. Tanner D. Angew. Chem. Int. Ed. Engl.: 1994; 33 599
96. Zwanenburg B., ten Holte P. Top. Curr. Chem.: 2001; 216 93
97. Couty F., Drouillat B., Evano G., David O. Eur. J. Org. Chem.: 2013; 2045
98. Bott T. M., West F. Heterocycles: 2012; 84 223
99. Alcaide B., Almendros P., Arangocillo C. Curr. Opin. Drug Discovery Dev.: 2010; 13 685
100. Couty F., Evano G. Synlett: 2009; 3053
101. Couty F., Evano G. Org. Prep. Proced. Int.: 2006; 38 427
102. De Kimpe N. Azetidines, Azetines, and Azetes: Monocyclic In Comprehensive Heterocyclic Chemistry II. Vol. 1B Padwa A., Katritzky A. R., Rees C. W., Scriven E. F. V. Chap. 1.18 Pergamon Elsevier Oxford: 1996; 507 589
103. Van Brabandt W., Mangelinckx S., D'hooghe M., Van Driessche B., De Kimpe N. Curr. Org. Chem.: 2009; 13 827
104. Van Brabandt W., Verniest G., De Smaele D., Duvey G., De Kimpe N. J. Org. Chem.: 2006; 71 7100
105. Minicone F., Rogers W. J., Green J. F., Khan M., Smith G. M., Bray C. D. Tetrahedron Lett.: 2014; 55 5890
106. McNally A., Haffemayer B., Collins B. S., Gaunt M. J. Nature: 2014; 510 129
107. Wang Z., Li F., Zhao L., He Q., Chen F., Zheng C. Tetrahedron: 2011; 67 9199
108. Van Hende E., Verniest G., Deroose F., Thuring J.-W, Macdonald G., De Kimpe N. J. Org. Chem.: 2009; 74 2250
109. Piron K., Verniest G., Van Hende E., De Kimpe N. ARKIVOC: 2012; (v) 6
110. Van Brabandt W., De Kimpe N. Synlett: 2006; 2039
111. Kenis S., D'hooghe M., Verniest G., Dang Thi T. A, Pham The C., Van Nguyen T., De Kimpe N. J. Org. Chem.: 2012; 77 5982
112. Ngoc Tam N. T., Magueur G., Ourévitch M., Crousse B., Bégué J.-P, Bonnet-Delpon D. J. Org. Chem.: 2005; 70 699
113. Jiang J., Shah H., DeVita R. J. Org. Lett.: 2003; 5 4101
114. Bravo P., Fustero S., Guidetti M., Volonterio A., Zanda M. J. Org. Chem.: 1999; 64 8731
115. Moiseev S. V., Goncharov V. M., Zatonsky G. V., Cherstkov V. F., Vasil'ev N. V. Mendeleev Commun.: 2006; 16 184
116. Shimada T., Ando T., Takagi T., Koyama M., Miki T., Kumadaki I. Chem. Pharm. Bull.: 1992; 40 1665
117. Katagiri N., Watanabe H., Kaneko C. Chem. Pharm. Bull.: 1988; 36 3354
118. Lensen N., Marais J., Brigaud T. Org. Lett.: 2015; 17 342
119. D'hooghe M., De Kimpe N. Synlett: 2006; 2089
120. Catak S., D'hooghe M., De Kimpe N., Waroquier M., Van Speybroeck V. J. Org. Chem.: 2010; 75 885
121. Mollet K., Broeckx L., D'hooghe M., De Kimpe N. Heterocycles: 2012; 84 431
122. Van Brabandt W., Van Landeghem R., De Kimpe N. Org. Lett.: 2006; 8 1105
123. Mollet K., Goossens H., Piens N., Catak S., Waroquier M., Tornroos K. W., Van Speybroeck V., D'hooghe M., De Kimpe N. Chem. Eur. J.: 2013; 19 3383