Porphyrins with exocyclic rings. Part 25: synthesis of porphyrins with a fused cyclic ether subunit from tetrahydro-4H-pyan-4-one

Tetrahedron

Volumn 66, Issue 25, 2010, Pages 4413-4422

  Smith, Breland E ^a   Lash, Timothy D ^a  

^a ILLINOIS STATE UNIVERSITY   (United States)

Author keywords

Conformational analysis; Crown ethers; Knorr pyrrole Synthesis; MacDonald condensation; Porphyrins

Indexed keywords

ACETOACETIC ACID; ACID; CROWN ETHER; ETHER DERIVATIVE; INDOLE DERIVATIVE; KETONE; METHANE; OXIME; PORPHYRIN DERIVATIVE; PROPIONIC ACID; PYRROLE DERIVATIVE; SODIUM DERIVATIVE; TETRAHYDROPYRAN DERIVATIVE; ZINC;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; POLYMERIZATION; PRIORITY JOURNAL; REACTION OPTIMIZATION; SYNTHESIS; TEMPERATURE;

EID: 77953122425     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.04.069     Document Type: Article

References (85)

1. Baker E.W., and Palmer S.E. In: Dolphin D. (Ed). The Porphyrins Vol. 1 (1978), Academic, New York, NY 486-552
2. Filby R.H., and Van Berkel G.J. In: Filby R.H., and Branthaver J.F. (Eds). Metal Complexes in Fossil Fuels. Geochemistry, Characterization, and Processing (1987), American Chemical Society, Washington, DC 2-37
3. Callot H.J. In: Scheer H. (Ed). The Chlorophylls (1991), CRC, Boca Raton 339-364
4. Callot H.J., and Ocampo R. In: Kadish K.M., Smith K.M., and Guilard R. (Eds). The Porphyrin Handbook Vol. 1 (2000), Academic, San Diego 349-398
5. Czernuszewicz R.S. J. Porphyrins Phthalocyanines 4 (2000) 426
6. Chicarelli M.I., Kaur S., and Maxwell J.R. In: Filby R.H., and Branthaver J.F. (Eds). Metal Complexes in Fossil Fuels. Geochemistry, Characterization, and Processing (1987), American Chemical Society, Washington, DC 40-67
7. Ocampo R., Callot H.J., and Albrecht P. In: Filby R.H., and Branthaver J.F. (Eds). Metal Complexes in Fossil Fuels. Geochemistry, Characterization, and Processing (1987), American Chemical Society, Washington, DC 68-73
8. Quirke J.M.E., and Maxwell J.R. Tetrahedron 36 (1980) 3453
9. Fookes C.J.R. J. Chem. Soc., Chem. Commun. (1985) 706
10. Chicarelli M.I., Wolff G.A., and Maxwell J.R. J. Chem. Soc., Chem. Commun. (1985) 723
11. Krane J., Skjetne T., Telnaes N., Bjoroy M., Schou L., and Solli H. Tetrahedron 39 (1983) 4109
12. Bonnett R., and Burke P.J. Geochim. Cosmochim. Acta 49 (1985) 1487
13. Boreham C.J., Fookes C.J.R., Popp B.N., and Hayes J.M. Geochim. Cosmochim. Acta 53 (1989) 2451
14. Huseby B., Barth T., and Ocampo R. Org. Geochem. 25 (1996) 273
15. Freeman D.H., Saint Martin D.C., and Boreham C.J. Energy Fuels 7 (1993) 194
16. Laycock J.D., Yost R.A., Wang L., and Quirke J.M.E. Energy Fuels 9 (1995) 1079
17. Cantú R., Stencel J.R., Czernuszewicz R.S., Jaffé P.R., and Lash T.D. Environ. Sci. Technol. 34 (2000) 192
18. Czernuszewicz R.S., Maes E.M., and Rankin J.G. In: Kadish K.M., Smith K.M., and Guilard R. (Eds). The Porphyrin Handbook Vol. 7 (2000), Academic, San Diego 293-337
19. Rankin J.G., Czernuszewicz R.S., and Lash T.D. Org. Geochem. 23 (1995) 419
20. Rankin J.G., Czernuszewicz R.S., and Lash T.D. Inorg. Chem. 34 (1995) 3025
21. Czernuszewicz R.S., Rankin J.G., and Lash T.D. Inorg. Chem. 35 (1996) 199
22. Rankin J.G., Cantú R., Czernuszewicz R.S., and Lash T.D. Org. Geochem. 30 (1999) 201
23. Boggess J.M., Czernuszewicz R.S., and Lash T.D. Org. Geochem. 33 (2002) 1111
24. Czader A., and Czernuszewicz R.S. Org. Geochem. 38 (2007) 250
25. Flaugh M.E., and Rapoport H. J. Am. Chem. Soc. 90 (1968) 6877
26. Chaudry I.A., Clezy P.S., and Mirza A.H. Aust. J. Chem. 33 (1980) 1095
27. Smith K.M., Langry K.C., and Minnetian O.M. J. Org. Chem. 49 (1984) 4602
28. Bauder C., Ocampo R., and Callot H.J. Tetrahedron 48 (1992) 5135
29. Clezy P.S., Fookes C.J.R., Prashar J.K., and Salek A. Aust. J. Chem. 45 (1992) 703
30. Bong I.C.C., Clezy P.S., Fookes C.J.R., Prashar J.K., and Salek A. Aust. J. Chem. 46 (1993) 1193
31. Clezy P.S., and Leung C.W.F. Aust. J. Chem. 46 (1993) 1705
32. Atkinson E.J., Clezy P.S., Leung C.W.F., Ramadan S., Salek A., and Zhuo M. Aust. J. Chem. 48 (1995) 1873
33. Clezy P.S., and Salek A. Aust. J. Chem. 49 (1996) 265
34. Baker E.W., Corwin A.H., Klesper E., and Wei P.E. J. Org. Chem. 33 (1968) 3144
35. Verne-Mismer J., Ocampo R., Callot H.J., and Albrecht P. Tetrahedron Lett. 27 (1986) 5257
36. Smith N.W., and Smith K.M. Energy Fuels 4 (1990) 675
37. Lash T.D. In: Moody C.J. (Ed). Advances in Nitrogen Heterocycles Vol. 1 (1995), JAI, Greenwich, Connecticut 19-51
38. Lash T.D. Org. Geochem. 14 (1989) 213
39. Lash T.D., Balasubramaniam R.P., Catarello J.J., Johnson M.C., May Jr. D.A., Bladel K.A., Feeley J.M., Hoehner M.C., Marron T.G., Nguyen T.H., Perun Jr. T.J., Quizon D.M., Shiner C.M., and Watson A. Energy Fuels 4 (1990) 668
40. Lash T.D., and Catarello J.J. Tetrahedron 49 (1993) 4159
41. Quizon-Colquitt D.M., and Lash T.D. J. Heterocycl. Chem. 30 (1993) 477
42. Li W., and Lash T.D. Tetrahedron Lett. 39 (1998) 8571
43. Lash T.D., Quizon-Colquitt D.M., Shiner C.M., Nguyen T.H., and Hu Z. Energy Fuels 4 (1993) 668
44. Zhang B., and Lash T.D. Tetrahedron Lett. 44 (2003) 7253
45. Lash T.D., Li W., and Quizon-Colquitt D.M. Tetrahedron 63 (2007) 12324
46. Lash T.D., Bladel K.A., and Johnson M.C. Tetrahedron Lett. 28 (1987) 1135
47. Lash T.D., Bladel K.A., Shiner C.M., Zajeski D.L., and Balasubramaniam R.P. J. Org. Chem. 57 (1992) 4809
48. Lash T.D., and Balasubramaniam R.P. Tetrahedron Lett. 31 (1990) 7545
49. Shiner C.M., and Lash T.D. Tetrahedron 61 (2005) 11628
50. Lash T.D. Tetrahedron Lett. 29 (1988) 6877
51. Lash T.D. Tetrahedron 54 (1998) 359
52. Lash T.D., and Johnson M.C. Tetrahedron Lett. 30 (1989) 5697
53. Lash T.D., and Perun Jr. T.J. Tetrahedron Lett. 28 (1987) 6265
54. Lash T.D., Nguyen T.H., and Hu Z. Synlett (1994) 905
55. Hu Z., and Lash T.D. Synlett (1994) 909
56. Bastian J.A., and Lash T.D. Tetrahedron 54 (1998) 6299
57. Chen S., and Lash T.D. J. Heterocycl. Chem. 34 (1997) 273
58. Lash T.D., and Chen S. Tetrahedron 61 (2005) 11577
59. Lash T.D., Marron T.G., and Bastian J.A. Tetrahedron 63 (2007) 12343
60. Gribble G.W. Knorr and Paal-Knorr pyrrole syntheses. In: Li J.J. (Ed). Name Reactions in Heterocyclic Chemistry (2005), Wiley, Hoboken, NJ 79-88
61. Thanaval V., and Krishnan V. J. Am. Chem. Soc. 104 (1982) 3643
62. For examples of porphyrins with appended crown ether units, see:
63. Gunter M.J., Johnston M.R., Skelton B.W., and White A.H. J. Chem. Soc., Perkin Trans. 1 (1984) 1009
64. Gunter M.J., and Johnston M.R. Tetrahedron Lett. 33 (1992) 1771
65. Kubo Y., Murai Y., Yamanaka J.-i., Tokita S., and Ishimaru Y. Tetrahedron Lett. 40 (1999) 6019
66. Jahan M., Safaria N., Khosravia H., Moghimi A., and Notash B. Polyhedron 24 (2005) 1682
67. Liu Y.-C., Kuo M.-C., Lee C.-W., Liang Y.-R., Lee G.-H., Peng S.-M., and Yeh C.-Y. Tetrahedron Lett. 49 (2008) 7223
68. Murashima T., Uchihara Y., Wakamori N., Uno H., Ogawa T., and Ono N. Tetrahedron Lett. 37 (1996) 3133
69. These results were presented, in part, at the following meetings:
70. Smith, B.E.; Lash, T.D. Book of Abstracts 233rd National American Chemical Society Meeting, Chicago, Illinois, March 2007; CHED 736.
71. Smith, B.E.; Lash, T.D. Book of Abstracts 235th National Meeting of the American Chemical Society, New Orleans, Louisiana, April 2008, ORGN 377.
72. Shvedov V.I., Altukhova L.P., and Grinev A.N. Khim. Geterotsikl. Soedin. (1972) 342
73. Rexhausen H., and Gossauer A. J. Chem. Soc., Chem. Commun. (1983) 275
74. Gossauer A. Bull. Soc. Chim. Belg. 92 (1983) 793
75. Arsenault G.P., Bullock E., and MacDonald S.F. J. Am. Chem. Soc. 82 (1960) 4384
76. Cavaleiro J.A.S., Rocha Gonsalves A.M.dA., Kenner G.W., and Smith K.M. J. Chem. Soc., Perkin Trans. 1 (1974) 1771
77. Lash T.D. Chem.-Eur. J. 2 (1996) 1197
78. Lash T.D., Chaney S.T., and Richter D.T. J. Org. Chem. 63 (1998) 9076
79. Lash T.D. J. Porphyrins Phthalocyanines 1 (1997) 29
80. Smith K.M. In: Smith K.M. (Ed). Porphyrins and Metalloporphyrins (1975), Elsevier, Amsterdam 3-28
81. Medforth C.J. In: Kadish K.M., Smith K.M., and Guilard R. (Eds). The Porphyrin Handbook Vol. 5 (2000), Academic, San Diego 1-80
82. Beresford G.D., and Stoddart J.F. Tetrahedron Lett. 21 (1980) 867
83. Lash T.D., Bellettini J.R., Bastian J.A., and Couch K.B. Synthesis (1994) 170
84. Smith K.M., and Minnetian O.M. J. Org. Chem. 50 (1985) 2073
85. Lash T.D., and Armiger Y.L.S.-T.-T. J. Heterocycl. Chem. 28 (1991) 965