Synthesis of meso-tetraphenyl porphyrins via condensation of dipyrromethanes with N-tosyl imines

Tetrahedron

Volumn 65, Issue 10, 2009, Pages 2043-2050

  Temelli, Baris ^a   Unaleroglu, Canan ^a  

^a HACETTEPE UNIVERSITY   (Turkey)

Author keywords

Dipyrromethane; Metal triflate; N Tosyl imine; Porphyrin

Indexed keywords

IMINE; METHANE; PORPHYRIN DERIVATIVE; PORPHYRINOGEN; SULFONAMIDE; TRIFLUOROMETHANESULFONIC ACID;

ALKYLATION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; OXIDATION; POLYMERIZATION; PRIORITY JOURNAL; SUBSTITUTION REACTION; SYNTHESIS;

EID: 59349087354     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.01.009     Document Type: Article

References (64)

1. Dolphin D. The Porphyrins Vols. 1-6 (1978), Academic, New York, NY
2. Milgrom L.R. The Colors of Life: An Introduction to the Chemistry of Porphyrins and Related Compounds (1997), Oxford University Press, Oxford
3. Sternberg E.D., and Dolphin D. Tetrahedron 54 (1998) 4151-4202
4. Pandey R.K. J. Porphyrins Phthalocyanines 4 (2000) 368-373
5. Macdonald I.J., and Dougherty T.J. J. Porphyrins Phthalocyanines 5 (2001) 105-129
6. Fairchild R.G., Kahl S.B., Laster B.H., Kalef-Ezra J., and Popenoe E.A. Cancer Res. 50 (1990) 4860-4865
7. Groves J.T. J. Porphyrins Phthalocyanines 4 (2000) 350-352
8. Bhyrappa P., Young J.K., Moore J.S., and Suslick K.S. J. Am. Chem. Soc. 118 (1996) 5708-5711
9. Groves J.T., and Viski P. J. Org. Chem. 55 (1990) 3628-3634
10. Mansuy D. Coord. Chem. Rev. 125 (1993) 129-142
11. Halterman R.L., and Mei X. Tetrahedron Lett. 37 (1996) 6291-6294
12. Balaz M., De Napoli M., Holmes A.E., Mammana A., Nakanishi K., Berova N., and Purrello R. Angew. Chem. 117 (2005) 4074-4077
13. Villari V., Mineo P., Micali N., Angelini N., Vitalini D., and Scamporrino E. Nanotechnology 18 (2007) 1-13
14. Zhang X.-B., Guo C.-C., Li Z.-Z., Shen G.-L., and Yu R.-Q. Anal. Chem. 74 (2002) 821-825
15. Deviprasad G.R., Keshavan B., and D'Souza F. J. Chem. Soc., Perkin Trans. 1 (1998) 3133-3135
16. Itagaki Y., Deki K., Nakashima S.-I., and Sadaoka Y. Sens. Actuators, B 108 (2005) 393-397
17. Rakow N.A., and Suslick K.S. Nature 406 (2000) 710-713
18. Tsuda A., and Osuka A. Science 293 (2001) 79-82
19. Liu Z., Yasseri A.A., Lindsey J.S., and Bocian D. Science 302 (2003) 1543-1545
20. Burrell A.K., and Wasielewski M.R. J. Porphyrins Phthalocyanines 4 (2000) 401-406
21. Kadish K.M., Smith K.M., and Guilard R. The Porphyrin Handbook Vol. 6 (2000), Academic, New York, NY
22. Armstrong N.R. J. Porphyrins Phthalocyanines 4 (2000) 414-417
23. Rothemund P. J. Am. Chem. Soc. 58 (1936) 625-627
24. Rothemund P. J. Am. Chem. Soc. 61 (1939) 2912-2915
25. Adler A.D., Longo F.R., Finarelli J.D., Goldmacher J., Assour J., and Korsakoff L. J. Org. Chem. 32 (1967) 476
26. Lindsey J.S., Hsu H.C., and Schreiman I.C. Tetrahedron Lett. 27 (1986) 4969-4970
27. Lindsey J.S., Schreiman I.C., Hsu H.C., Kearney P.C., and Marguerettaz A.M. J. Org. Chem. 52 (1987) 827-836
28. Lindsey J.S., and Wagner R.W. J. Org. Chem. 54 (1989) 828-836
29. Lindsey J.S., MacCrum K.A., Tyhonas J.S., and Chuang Y.-Y. J. Org. Chem. 59 (1994) 579-587
30. Lee C.-H., and Lindsey J.S. Tetrahedron 50 (1994) 11427-11440
31. Wagner R.W., Johnson T.E., and Lindsey J.S. Tetrahedron 53 (1997) 6755-6790
32. Li F., Yang K., Tyhonas J.S., MacCrum K.A., and Lindsey J.S. Tetrahedron 53 (1997) 12339-12360
33. Onaka M., Shinoda T., Izumi Y., and Nolen E. Chem. Lett. (1993) 117-120
34. Gradillas A., Del Campo C., Sinisterra J.V., and Llama E.F. J. Chem. Soc., Perkin Trans. 1 (1995) 2611-2613
35. Furusho Y., Kimura T., Mizuno Y., and Aida T. J. Am. Chem. Soc. 119 (1997) 5267-5268
36. Wang Q.M., and Bruce D.W. Tetrahedron Lett. 37 (1996) 7641-7644
37. Nishino N., Wagner R.W., and Lindsey J.S. J. Org. Chem. 61 (1996) 7534-7544
38. Geier III G.R., Littler B.J., and Lindsey J.S. J. Chem. Soc., Perkin Trans. 2 (2001) 701-711
39. Littler B.J., Ciringh Y., and Lindsey J.S. J. Org. Chem. 64 (1999) 2864-2872
40. Fox S., Hudson R., and Boyle R.W. Tetrahedron Lett. 44 (2003) 1183-1185
41. Friedman M. J. Org. Chem. 30 (1965) 859-863
42. Whitlock H.W., and Hanauer R. J. Org. Chem. 33 (1968) 2169-2171
43. Nguyen L.T., Senge M.O., and Smith K.M. Tetrahedron Lett. 35 (1994) 7581-7584
44. Nguyen L.T., Senge M.O., and Smith K.M. J. Org. Chem. 61 (1996) 998-1003
45. Siri O., and Smith K.M. Tetrahedron Lett. 44 (2003) 6103-6105
46. Fan D., Taniguchi M., Yao Z., Dhanalekshmi S., and Lindsey J.S. Tetrahedron 61 (2005) 10291-10302
47. Tabushi I., Sakai K.-I., and Yamamura K. Tetrahedron Lett. 19 (1978) 1821-1824
48. Unaleroglu C., Temelli B., and Demir A.S. Synthesis 15 (2004) 2574-2578
49. Temelli B., and Unaleroglu C. Tetrahedron Lett. 46 (2005) 7941-7943
50. Unaleroglu C., and Yazici A. Tetrahedron 63 (2007) 5608-5613
51. Unaleroglu C., Aytac S., and Temelli B. Heterocycles 71 (2007) 2427-2440
52. Temelli B., and Unaleroglu C. Tetrahedron 62 (2006) 10130-10135
53. Kobayashi S., Sugiura M., Kitagawa H., and Lam W.W.-L. Chem. Rev. 102 (2002) 2227-2302
54. Kobayashi S. Synlett (1994) 689-701
55. Luo S., Zhu L., Talukdar A., Zhang G., Mi X., Cheng J.-P., and Wang P.G. Mini-Rev. Org. Chem. 2 (2005) 546-564
56. Geier III G.R., Ciringh Y., Li F., Haynes D.M., and Lindsey J.S. Org. Lett. 2 (2000) 1745-1748
57. Zaidi S.H.H., Fico R.M., and Lindsey J.S. Org. Prosess Res. Dev. 10 (2006) 118-134
58. Arsenault G.P., Bullock E., and MacDonald S.F. J. Am. Chem. Soc. 82 (1960) 4384-4389
59. Lee C.-H., Li F., Iwamoto K., Dadok J., Bothner-By A.A., and Lindsey J.S. Tetrahedron 51 (1995) 11645-11672
60. Sessler J.L., Capuano V.L., and Harriman A. J. Am. Chem. Soc. 115 (1993) 4618-4628
61. Wallace D.M., Leung S.H., Senge M.O., and Smith K.M. J. Org. Chem. 58 (1993) 7245-7257
62. DiMagro S.G., and Williams R.A. J. Org. Chem. 59 (1994) 6943-6948
63. Naik R., Joshi P., Kaiwar S.P., and Deshpande R.K. Tetrahedron 59 (2003) 2207-2213
64. Sharghi H., and Nejad A.H. Tetrahedron 60 (2004) 1863-1868