Towards a green synthesis of isoquinoline: Beckmann rearrangement of E,E-cinnamaldoxime over H-zeolites

Microporous and Mesoporous Materials

Volumn 102, Issue 1-3, 2007, Pages 138-150

  Thomas, Bejoy ^a,b   Prabhu, Uday R ^b   Prathapan, S ^a   Sugunan, S ^a  

^a Department of Physics   (India)

^b INDIAN INSTITUTE OF SCIENCE   (India)

Author keywords

Beckmann rearrangement; Cinnamaldehyde; Cinnamaldoxime; Cinnamo nitrile; E Z isomerization; Isoquinoline; Zeolites

Indexed keywords

ALDEHYDES; CATALYSTS; ELECTRONS; HYDROLYSIS; SYNTHESIS (CHEMICAL);

BECKMANN REARRANGEMENT; CINNAMALDEHYDE; CINNAMALDOXIME; CINNAMO-NITRILE;

ZEOLITES;

ALDEHYDES; CATALYSTS; ELECTRONS; HYDROLYSIS; SYNTHESIS (CHEMICAL); ZEOLITES;

EID: 34247139883     PISSN: 13871811     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.micromeso.2006.12.006     Document Type: Article

References (99)

1. McDonald M.C., Filipe H.M., Wright J.A., Abdelrahman M., Threadgill M.D., Thompson A.S., and Thiemermann C. British J. Pharma. 130 (2000) 843-850
2. White A.W., Almassy R., Calvert A.H., Curtin N.J., Griffin R.J., Hostomsky Z., Maegley K., Newell D.R., Srinivasan S., and Golding B.T. J. Med. Chem. 43 (2000) 4084-4097
3. Thiemermann C., Bowes J., Myint F.P., and Vane J.R. Proc. Natl. Acad. Sci. 94 (1997) 679-683
4. Soriano F.G., Virág L., Jagtap P., Szabó E., Mabley J.G., Liaudet L., Marton A., Hoyt D.G., Murthy K.G.K., Salzman A.L., Southan G.J., and Szabó C. Nat. Med. 7 (2001) 108-113
5. Abdelkarim G.E., Gertz K., Harms C., Katchanov J., Dirnagl U., Szabó C., and Endres M. Int. J. Mol. Med. 7 (2001) 255-260
6. Pero R.W., Axelsson B., Siemann D., Chaplin D., and Dougherty G. Mol. Cell. Biochem. 193 (1999) 119-125
7. Alexandrova R., Varadinova T., Velcheva M., Genova P., and Sainova I. Bulg. Acad. Sci. 4 (2000) 8-12
8. Nagatsu T. Neurosci. Res. 29 (1997) 99-111
9. Gilchrist T.L. Heterocyclic Chemistry. 3rd ed. (1997), Addison Wesley Longman, Essex, UK
10. Page P.B., Rassias G.A., Barros D., Bethell D., and Schilling M.B. J. Chem. Soc. Perkin Trans. 19 1 (2000) 3325-3334
11. Harris J., and Pope W.J. J. Chem. Soc. 121 (1922) 1029-1033
12. Katritsky A.R., and Pozharskii A.F. Handbook of Heterocyclic Chemistry. 2nd ed. (2000), Elsevier, Oxford, UK
13. In: Katritsky A.R., Rees C.W., and Scriven E.F. (Eds). Comprehensive Heterocyclic Chemistry II: A Review of the Literature 1982-1995 vol. 5 (1996), Elsevier, Tarrytown, NY
14. Bischler A., and Napieralski B. Chem. Ber. 26 (1893) 1903
15. Manske R.H. Chem. Rev. 30 (1942) 145-158
16. Bergstrom F.W. Chem. Rev. 35 (1944) 77-277 and references therein
17. Rozwadowska M.D. Heterocycles 39 (1994) 903
18. W.M. Whaley, T.R. Govindachari, in: R. Adams (Ed.), Organic Reactions, vol. 6, 1951, pp. 151-158.
19. Whaley W.M., and Hartung W.H. J. Org. Chem. 14 (1949) 650-654
20. Forsyth R., Kelly C.I., and Pyman F.L. J. Chem. Soc. 127 (1925) 1659-1667
21. Mori M., Wakamatsu H., Tonogaki K., Fujita R., Kitamura T., and Sato Y. J. Org. Chem. 70 (2005) 1066-1069
22. Clayden J., Greeves N., Warren S., and Wothers P. Chemistry (2001), Oxford University Press, Oxford, NewYork pp. 1212
23. Herz W., and Tsai L. J. Am. Chem. Soc. 77 (1955) 3529-3533
24. Staub P. Helv. Chim. Acta 5 (1922) 888-894
25. Buck J.S. J. Am. Chem. Soc. 56 (1934) 1769-1771
26. Kido K., and Watanabe Y. J. Pharm. Soc. Jpn. 95 (1975) 1038
27. Mori M., Wakamatsu H., Tonogaki K., Fujita R., Kitamura T., and Sato Y. J. Org. Chem. 70 (2005) 1066-1069
28. Tsutsui H., and Narasaka K. Chem. Lett. (2001) 526-527
29. Corma A., and Garca H. Chem. Rev. 103 (2003) 4307-4365
30. Dupont J., de Souza R.F., and Suarez P.A.Z. Chem. Rev. 102 (2002) 3667-3691
31. de Vries J.G. Can. J. Chem. 79 (2001) 1086-1092
32. Corma A., and Garcia H. Chem. Rev. 102 (2002) 3837-3892
33. Davis M.E. Nature 417 (2002) 813-821
34. Tosheva L., and Valtchev V.P. Chem. Mater. 17 (2005) 2494-2513
35. Avalos M., Babiano R., Cintas P., Jimenez J.L., and Palacios J.C. Angew. Chem. Int. Ed. 45 (2006) 3904-3908
36. Trost B.M. Science 254 (1991) 1471-1477
37. Angew. Chem. Int. Ed. Engl. 34 (1995) 259-281
38. Enache D.I., Edwards J.K., Landon P., Espriu B.S., Carley A.F., Herzing A.A., Watanabe M., Kiely C.J., Knight D.W., and Hutchings G.J. Science 331 (2006) 362-365
39. Yu W., Bian F., Gao Y., Yang L., and Liu Z.-L. Adv. Synth. Catal. 348 (2006) 59-62
40. Collins T. Science 291 (2001) 48-49
41. Thomas B., Prathapan S., and Sugunan S. Appl. Catal. A: Gen. 277 (2004) 247-252
42. Thomas B., Prathapan S., and Sugunan S. Micropor. Mesopor. Mater. 79 (2004) 21-27
43. Thomas B., and Sugunan S. Micropor. Mesopor. Mater. 72 (2004) 227-238
44. Thomas B., Prathapan S., and Sugunan S. Micropor. Mesopor. Mater. 84 (2005) 137-143
45. Encyclopedia of Chemical Technology, 4th ed., Wiley, New York, 1992, pp. 827-838.
46. Dalhhoff G., Niederer J.P.M., and Hölderich W.F. Catal. Rev. Sci. Eng. 43 (2001) 381-441
47. Heitmann G.P., Dahlhoff G., Niederer J.P.M., and Hölderich W.F. J. Catal. 194 (2000) 122-129
48. Heitmann G.P., Dahlhoff G., and Hölderich W.F. J. Catal. 186 (2000) 12-19
49. Takahashi T., Nishi M., Tagawa Y., and Kai T. Micropor. Mater. 3 (1995) 467-471
50. Ichihashi H., and Kitamura M. Catal. Today 73 (2002) 23-28
51. Ichihashi H., and Sato H. Appl. Catal. A: Gen. 221 (2001) 359-366
52. Kitamura M., and Ichihashi H. Stud. Surf. Sci. Catal. 90 (1994) 67-70
53. Ichihashi H. Stud. Surf. Sci. Catal. 145 (2003) 73-78
54. Takahashi T., Nasution M.N.A., and Kai T. Appl. Catal. A: Gen. 210 (2001) 339-344
55. Thomas J.M., and Raja R. Proc. Natl. Acad. Sci. 102 (2005) 13732-13736
56. Forni L., Fornasari G., Giordano G., Lucarelli C., Katovic A., Trifiro F., Perri C., and Nagy J.B. Phys. Chem. Chem. Phys. 6 (2004) 1842-1847
57. Conesa T.D., Hidalgo J.M., Luque R., Campelo J.M., and Romero A.A. Appl. Catal. A: Gen. 299 (2006) 224-234
58. Tatsumi T. In: Sheldon R.A., and van Bekkum H. (Eds). Fine Chemicals through Heterogeneous Catalysis (2001), Wiley-VCH 185-204
59. Röseler J., Heitmann G., and Hölderich W.F. Stud. Surf. Sci. Catal. 105 (1997) 1173-1180
60. Guo S., Du Z., Zhang S., Li D., Li Z., and Deng Y. Green Chem. 8 (2006) 296-300
61. Candeias N.R., and Afonso C.A.M. J. Mol. Catal. A: Chem. 242 (2005) 195-217
62. Camblor M.A., Corma I A., Garci{dotless}a H., Semmer-Herledan V., and Valencia S. J. Catal. 177 (1998) 267-272
63. Fernandez A.B., Boronat M., Balsco T., and Corma A. Angew. Chem. Int. Ed. 44 (2005) 2370-2373
64. Greenwood N.N., and Earnshaw A. Chemistry of the Elements. 2nd ed. (1997), Butterworth-Heinemann, Oxford pp. 345-346
65. Cotton F.A., Wilkinson G., Murillo C.A., and Bochmann M. Advanced Inorganic Chemistry. 6th ed. (1999), John Wiley and Sons Inc., New York pp. 178-179
66. Dumitriu E., and Hulea V. J. Catal. 218 (2003) 249-257
67. Anand R., Khomane R.B., Rao B.S., and Kulkarni B.D. Catal. Lett. 78 (2002) 189-194
68. Komatsu T., Maeda T., and Yashima T. Micropor. Mesopor. Mater. 35-36 (2000) 173-180
69. Yashima T., Oka N., and Komatsu T. Catal. Today 38 (1997) 249-253
70. Meier W.M. Z. Krist. 115 (1961) 439-450
71. Baur W.H. Am. Miner. 49 (1964) 697-704
72. Olson D.H., Kokotailo G.T., Lawton S.L., and Meier W.M. J. Phys. Chem. 85 (1981) 2238-2243
73. Tekewaki T.L., Beck W., and Davis M.E. Topics Catal. 9 (1999) 35-42
74. Ramaswamy A.V. Sci. Tech. Chim. Ind. (2000) 1-9
75. Landis P.S., and Venuto P.B. J. Catal. 6 (1966) 245-252
76. Aucejo A., Burguet M.C., Corma A., and Fornes V. Appl. Catal. 22 (1986) 187-200
77. Sato H. Catal. Rev. Sci. Eng. 39 (1997) 395-424
78. Hölderich W.F. Stud. Surf. Sci. Catal. 46 (1989) 193-209
79. Ngamchahaussirichai C., Wu P., and Tatsumi T. J. Catal. 235 (2005) 139-149
80. Fernández A.-B., Marinas A., Blasco T., Fornés V., and Corma A. J. Catal. 243 (2006) 270-277
81. O'Sullivan P., Forni L., and Hodnett B.K. Ind. Eng. Chem. Res. 40 (2001) 1471-1475
82. Catanach J., Wu E.L., and Venuto P.B. J. Catal. 11 (1968) 342-347
83. Lok B.M., Marcus B.K., and Angell C.L. Zeolites 6 (1986) 185-194
84. Camblor M.A., Corma A., Garci{dotless}́a H., Semmer-Herlédan V., and Valencia S. J. Catal. 177 (1998) 267-272
85. Ngamcharussrivichai C., Wu P., and Tatsumi T. Appl. Catal. A: Gen. 288 (2005) 158-168
86. Ngamcharussrivichai C., Wu P., and Tatsumi T. J. Catal. 227 (2004) 448-458
87. Guisnet M., and Magnoux P. Appl. Catal. 54 (1989) 1-27
88. Liang W., Jin Y., Yu Z., Wang Z., Han B., He M., and Min E. Zeolites 17 (1996) 297-303
89. Dalton D.B., and Foley H.G. J. Org. Chem. 38 (1973) 4200-4202
90. Frisch H.L., Hyuang L., and Zeng W. J. Membr. Sci. 170 (2000) 35-41
91. Lalitha A., Pitchumani K., Kannan P., and Srinivasan C. Tetrahedron 54 (1998) 15667-15672
92. Kojma M., Takeya H., Kuriyama Y., and Oishi S. Chem. Lett. 10 (1997) 997-1998
93. Kiyoshi O., Manda J., and Morikawa A. J. Chem. Soc. Faraday Trans. 1 77 (1981) 569-574
94. Kiyoshi O., Oouchi R., and Morikawa A. J. Catal. 50 (1977) 379-381
95. Kiyoshi O., and Oouchi R. J. Catal. 46 (1977) 71-81
96. Nguyen M.T., Raspoet G., and Vanquickenborne L.G. J. Am. Chem. Soc. 119 (1997) 2552-2562
97. Bucko T., Hafner J., and Benco L. J. Phys. Chem. A 108 (2004) 11388-11397
98. Hirschl R., Eichler A., and Hafner J. J. Catal. 226 (2004) 273-282
99. Shinohara Y., Mae S., Shouro D., and Nakajima T. J. Mol. Struct. 497 (2000) 1-9