Synthesis of N-tetrasubstituted cyclam derivatives appended with sulfonyl or sulfinyl groups via aza-Michael addition

Tetrahedron

Volumn 63, Issue 41, 2007, Pages 10330-10336

  de Castries, Augustin ^a   Escande, Aude ^a   Fensterbank, Hélène ^a   Magnier, Emmanuel ^a   Marrot, Jérôme ^a   Larpent, Chantal ^a  

^a UNIVERSITÉ DE VERSAILLES SAINT QUENTIN EN YVELINES   (France)

Author keywords

Azamacrocycles; Coordination complexes; Vinylsulfone; Vinylsulfoxide

Indexed keywords

1,4,8,11 TETRAKIS(2 PARA TOLYLSULFINYLETHYL) 1,4,8,11 TETRAAZACYCLOTETRADECANE; 1,4,8,11 TETRAKIS(2 PHENYLSULFINYLETHYL) 1,4,8,11 TETRAAZACYCLOTETRADECANE; 1,4,8,11 TETRAKIS(2 PHENYLSULFONYLETHYL) 1,4,8,11 TETRAAZACYCLOTETRADECANE; 1,4,8,11 TETRAKIS(2 PHENYLSULFONYLETHYL) 1,4,8,11 TETRAAZACYCLOTETRADECANE COPPER(II) NITRATE 6 CU(II); 2 PROPANOL; AZAMACROCYCLE; CUPRIC ION; CYCLAM DERIVATIVE; EUROPIUM; MACROCYCLIC COMPOUND; UNCLASSIFIED DRUG;

ARTICLE; CRYSTAL STRUCTURE; MICHAEL ADDITION; PRIORITY JOURNAL; SUBSTITUTION REACTION; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 34548288052     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.07.067     Document Type: Article

References (108)

1. Liang X., and Sadler P.J. Chem. Soc. Rev. 33 (2004) 246-265
2. Izatt R.M., Pawlak K., Bradshaw J.S., and Bruening R. Chem. Rev. 91 (1991) 1721-2085
3. Alexander V. Chem. Rev. 95 (1995) 273-342
4. Bottrill M., Kwok L., and Long N.J. Chem. Soc. Rev. 35 (2006) 557-571
5. Helm L., and Merbach A.E. Chem. Rev. 105 (2005) 1923-1959
6. Lukes I., Kotek J., Vojtisek P., and Hermann P. Coord. Chem. Rev. 216 (2001) 287-312
7. Busch D.H. Acc. Chem. Res. 11 (1978) 392-400
8. Parker D. Chem. Soc. Rev. 19 (1990) 271-291
9. Parker D. Chem. Britain (1994) 818-822
10. De Clercq E. Mini-Rev. Med. Chem. 5 (2005) 805-824
11. Caravan P. Chem. Soc. Rev. 35 (2006) 512-523
12. Elias H. Coord. Chem. Rev. 187 (1999) 37-73
13. Bakaj M., and Zimmer M. J. Mol. Struct. 508 (1999) 59-72
14. Thom V.J., Boeyens J.C.A., McDougall G.J., and Hancock R.D. J. Am. Chem. Soc. 106 (1984) 3198-3207
15. Thom V.J., Hosken G.D., and Hancock R.D. Inorg. Chem. 24 (1985) 3378-3381
16. Meyer M., Dahaoui-Gindrey V., Lecomte C., and Guilard R. Coord. Chem. Rev. 178-180 (1998) 1313-1405
17. Lecomte C., Dahaoui-Gindrey V., Chollet H., Gros C., Mishra A.K., Barbette F.P., Pullumbi P., and Guilard R. Inorg. Chem. 36 (1997) 3827-3838
18. Liu W., Jiao T., Li Y., Liu Q., Tan M., Wang H., and Wang L. J. Am. Chem. Soc. 126 (2004) 2280-2281
19. Moulin C., Larpent C., and Gazeau D. Anal. Chim. Acta 378 (1999) 47-54
20. Corriu R.J.P., Embert F., Guari Y., Reye C., and Guilard R. Chem.-Eur. J. 8 (2002) 5732-5741
21. Finocchiaro A., Failla S., and Consiglio G. Russ. Chem. Bull. 54 (2005) 1355-1372
22. Svobodova I., Lubal P., Plutnar J., Havlicklova J., Kotek J., Hermann P., and Lukes I. Dalton Trans 43 (2006) 5184-5197
23. de Castries A., Magnier E., Monmotton S., Fensterbank H., and Larpent C. Eur. J. Org. Chem. 20 (2006) 4685-4692
24. Pozzi G., Cavazzini M., and Quici S. Tetrahedron Lett. 38 (1997) 7605-7608
25. Larpent C., Laplace A., and Zemb T. Angew. Chem., Int. Ed. 43 (2004) 3163-3167
26. Larpent C., Laplace A., and Zemb T. Angew. Chem. 116 (2004) 3225-3229
27. Arleth L., Posselt D., Gazeau D., Larpent C., Zemb T., Mortensen K., and Pedersen J.S. Langmuir 13 (1997) 1887-1896
28. Fensterbank H., Berthault P., and Larpent C. Eur. J. Org. Chem. 20 (2003) 3985-3990
29. Fensterbank H., Zhu J., Riou D., and Larpent C. J. Chem. Soc. Perkin Trans. 1 (1999) 811-816
30. Gaudinet-Hamann B., Zhu J., Fensterbank H., and Larpent C. Tetrahedron Lett. 40 (1999) 287-290
31. Tschudin D., Basak A., and Kaden T.A. Helv. Chim. Acta 71 (1988) 100-106
32. Koshti N., Gantla V.R., Jacobs H., and Gopalan A. Synth. Commun. 32 (2002) 3779-3790
33. Wainwright K.P. J. Chem. Soc., Dalton Trans. (1980) 2117-2120
34. Freeman G.M., Barefield E.K., and Van Derver D.G. Inorg. Chem. 23 (1984) 3092-3103
35. Gros C., Chollet H., Mishra A.K., and Guilard R. Synth. Commun. 26 (1996) 35-47
36. Koshti N.M., Jacobs H.K., Martin P.A., Smith P.H., and Gopalan A.S. Tetrahedron Lett. 35 (1994) 5157-5160
37. Collman J.P., Zhang X., Herrmann P.C., Uffelman E.S., Boitrel B., Straumanis A., and Brauman J.I. J. Am. Chem. Soc. 116 (1994) 2681-2682
38. Bulach V., Mandon D., and Weiss R. Angew. Chem., Int. Ed. Engl. 30 (1991) 572-575
39. Stephan H., Geipel G., Appelhans D., Bernhard G., Tabuani D., Komber H., and Voit B. Tetrahedron Lett. 46 (2005) 3209-3212
40. Bulach V., Mandon D., Fischer J., and Weiss R. Inorg. Chim. Acta 210 (1993) 7-9
41. Simpkins N.S. Tetrahedron 46 (1990) 6951-6984
42. Simpkins N.S. In: Baldwin J.E., and Magnus P.D. (Eds). Sulfones in Organic Synthesis, Tetrahedron Organic Chemistry Series Vol. 10 (1993), Pergamon, Oxford
43. In: Patai S., Rappoport Z., and Stirling C.J. (Eds). The Chemistry of Functional Groups: The Chemistry of Sulfones and Sulfoxides (1998), Wiley, Chichester, UK
44. Durst T. In: Barton D.H.R., and Ollis W.D. (Eds). Comprehensive Organic Chemistry (1979), Pergamon, Oxford 171-213
45. Shenhav H., Rappoport Z., and Patai S. J. Chem. Soc. B (1970) 469-476
46. Enders D., Saint-Dizier A., Lannou M.-I., and Lenzen A. Eur. J. Org. Chem. 1 (2006) 29-49 and references therein
47. Magnier-Bouvier C., Blazejewski J.-C., Larpent C., and Magnier E. Tetrahedron Lett. 51 (2006) 9121-9124
48. Enders D., Müller S.F., Raabe G., and Runsik J. Eur. J. Org. Chem. 6 (2000) 879-892 and references therein
49. Mc Dowell S.T., and Stirling C.J.M. J. Chem. Soc. B (1967) 343-348
50. Reddick J.J., Cheng J., and Roush W.R. Org. Lett. 5 (2003) 1967-1970
51. Ravindran B., Deshpande S.G., and Pathak T. Tetrahedron 57 (2001) 1093-1098
52. Ravindran B., Sakthivel K., Cheravakkattu G.S., and Pathak T. J. Org. Chem. 65 (2000) 2637-2641
53. Das I., Pathak T., and Suresh C.G. J. Org. Chem. 70 (2005) 8047-8054
54. Wu J.-C., Pathak T., Tong W., Vial J.-M., Remaud G., and Chattopadhyaya J. Tetrahedron 44 (1988) 6705-6722
55. Bera S., Sakthivel T., Pathak T., and Langley G.J. Tetrahedron 51 (1995) 7857-7866
56. Kroll F.E., Morphy R., Rees D., and Gani D. Tetrahedron Lett. 38 (1997) 8573-8576
57. Lutolf M.P., and Hubbell J.A. Biomacromolecules 4 (2003) 713-722
58. Zhen G., Falconnet D., Kuennemann E., Vörös J., Spencer N.D., Textor M., and Zürcher S. Adv. Funct. Mater. 16 (2006) 243-251
59. Teyssot M.-L., Fayolle M., Philouze C., and Dupuy C. Eur. J. Org. Chem. 1 (2003) 54-62 and references therein
60. Bera S., Langley G.J.L., and Pathak T. J. Org. Chem. 63 (1998) 1754-1760
61. Padwa A., and Norman B.H. J. Org. Chem. 55 (1990) 4801-4807
62. Gao C., and Yan D. Chem. Commun. (2001) 107-108
63. Zheng Z., Pan C., Wang D., and Liu Y. Macromol. Chem. Phys. 206 (2005) 2182-2189
64. de Vicente J., Arrayas R.G., and Carretero J.C. Tetrahedron Lett. 40 (1999) 6083-6086
65. Alonso D.A., Costa A., Mancheno B., and Najera C. Tetrahedron 53 (1997) 4791-4814
66. Back T.G., Parvez M., and Zhai H. J. Org. Chem. 68 (2003) 9389-9393
67. Pyne S.G., Griffith R., and Edwards M. Tetrahedron Lett. 29 (1988) 2089-2092
68. Kahn S.D., and Hehre W.J. J. Am. Chem. Soc. 108 (1986) 7399-7400
69. Abbot D.J., Colonna S., and Stirling C.J.M. J. Chem. Soc., Chem. Commun. (1971) 471-471
70. Matsuyama H., Itoh N., Matsumoto A., Ohira N., Hara K., Yoshida M., and Iyoda M. J. Chem. Soc. Perkin Trans. 1 (2001) 2924-2930
71. Pyne S.G., Bloem P., and Griffith R. Tetrahedron 45 (1989) 7013-7022
72. Ronan B., and Kagan H.B. Tetrahedron: Asymmetry 3 (1992) 115-122
73. Naidu B.N., Sorenson M.E., Connolly T.P., and Ueda Y. J. Org. Chem. 68 (2003) 10098-10102
74. Ranu B.C., and Banerjee S. Tetrahedron Lett. 48 (2007) 141-143
75. Patin H., and Larpent C. Tetrahedron 44 (1988) 6107-6118
76. Larpent C., Meignan G., and Patin H. Tetrahedron Lett. 32 (1991) 2615-2618
77. Larpent C., Meignan G., and Patin H. Tetrahedron 46 (1990) 6381-6398
78. Larpent C., and Patin H. Tetrahedron Lett. 29 (1988) 4577-4580
79. Larpent C., Geniès C., Delgado A.-P., Caminade A.-M., Majoral J.-P., Sassi J.-F., and Leising F. Chem. Commun. (2004) 1816-1817
80. Dong Y., Lawrance G.A., Lindoy L.F., and Turner P. Dalton Trans. 8 (2003) 1567-1576
81. Buxtorf R., and Kaden T.A. Helv. Chim. Acta 57 (1974) 1035-1042
82. Amatore C., Barbe J.-M., Bucher C., Duval E., Guilard R., and Verpeaux J.-N. Inorg. Chim. Acta 356 (2003) 267-278
83. Bucher C., Duval E., Barbe J.-M., Verpeaux J.-N., Amatore C., and Guilard R. C.R. Acad. Sci., Ser. IIc: Chim. 3 (2000) 211-222
84. El Ghachtouli S., Cadiou C., Deschamps-Olivier I., Chuburu F., Aplincourt M., and Roisnel T. Eur. J. Inorg. Chem. 17 (2006) 3472-3481
85. Comparone A., and Kaden T.A. Helv. Chim. Acta 81 (1998) 1765-1772
86. Studder M., and Kaden T.A. Helv. Chim. Acta 69 (1986) 2081
87. Chapman J., Ferguson G., Gallagher J.F., Jennings M.C., and Parker D.J. J. Chem. Soc., Dalton Trans. 3 (1992) 345-353
88. Calligaris M. Coord. Chem. Rev. 318 (2004) 351-375
89. Niyama E., Brito H.F., Cremona M., Teotonio E.E.S., Reyes R., Brito G.E.S., and Felinto M.C.F.C. Spectrochim. Acta, Part A 61 (2005) 2643-2649
90. Malta O.L., Brito H.F., Menezes J.F.S., Goncalves e Silva F.R., Alves Jr. S., Farias Jr. F.S., and de Andrade A.V.M. J. Lumin. 75 (1997) 255-268
91. Umeda K., Isolani P.C., Zaim M.H., and Vicentini G. J. Alloys Compd. 344 (2002) 80-82
92. Brito H.F., Malta O.L., and Menezes J.F.S. J. Alloys Compd. 303-304 (2000) 336-339
93. Carvalho A., Domingos A., Isolani P.C., Marques N., Pires de Matos A., and Vicentini G. Polyhedron 19 (2000) 1707-1712
94. Li J.R., Bu X.H., and Zhang R.H. Inorg. Chem. 43 (2004) 237-244
95. Li J.-R., Bu X.-H., Zhang R.-H., Duan C.-Y., Wong K.M.-C., and Yam V.W.-W. New J. Chem. 28 (2004) 261-265
96. Zhang R.-H., Ma B.-Q., Bu X.-H., Wang H.-G., and Yao X.-K. Polyhedron 16 (1997) 1123-1127
97. Li J.R., Bu X.H., and Zhang R.H. Eur. J. Inorg. Chem. 8 (2004) 1701-1704
98. Bu X.-H., Weng W., Li J.-R., Chen W., and Zhang R.-H. Inorg. Chem. 41 (2002) 413-415
99. Zhang R.-H., Ma B.-Q., Bu X.-H., Wang H.-G., and Yao X.-K. Polyhedron 16 (1997) 1787-1792
100. Ayala D., Bombieri G., Del Pra A., and Vicentin G. lnorg. Chim. Acta 274 (1998) 236-238
101. Prenesti E., Daniele P.G., Berto S., and Toso S. Polyhedron 25 (2006) 2815-2823
102. See Supplementary data for comparison of IR spectra.
103. Lei K.-W., and Liu W.-S. Spectrochim. Acta, Part A 65 (2006) 187-190
104. Leonard J.P., dos Santos C.M.G., Plush S.E., Mc Cabe T., and Gunnlaugsson T. Chem. Commun. (2007) 129-131
105. Gunnlaugsson T., and Leonard J.P. Chem. Commun. (2005) 3114-3131
106. Sheldrick G.M. SADABS, Program for Scaling and Correction of Area Detector Data (1997), University of Göttingen, Göttingen (Germany)
107. Blessing R.H. Acta Cryst A 51 (1995) 33
108. Sheldrick G.M. SHELX-TL, Version 6.14 (2003), University of Göttingen, Bruker AXS, Madison, WI