Green chemistry for preparation of oligopyrrole macrocycles precursors: Novel methodology for dipyrromethanes and tripyrromethanes synthesis in water

Collection of Czechoslovak Chemical Communications

Volumn 69, Issue 5, 2004, Pages 1126-1136

  Král, Vladimír ^a   Vašek, Petr ^a   Dolenský, Bohumil ^a  

^a INSTITUTE OF CHEMICAL TECHNOLOGY   (Czech Republic)

Author keywords

Aldehydes; Calixpyrrols; Condensation in water; Dipyrromethanes; Green chemistry; Oligopyrrole macrocycles; Porphyrins; Pyrrols; Tripyromethanes

Indexed keywords

ALDEHYDE DERIVATIVE; KETONE; MACROCYCLIC COMPOUND; METHANE; ORGANIC SOLVENT; PYRROLE DERIVATIVE; WATER;

ARTICLE; CATALYSIS; CATALYST; POLYMERIZATION; PRECIPITATION; ROOM TEMPERATURE; SYNTHESIS; TEMPERATURE SENSITIVITY;

EID: 3242754255     PISSN: 00100765     EISSN: None     Source Type: Journal    
DOI: 10.1135/cccc20041126     Document Type: Article

References (38)

1. Neya S., Funasaki N.: J. Heterocycl. Chem. 1997, 34, 689.
2. Da Silva F. M., Jones J., Jr.: J. Brazilian Chem. Soc. 2001, 12, 135.
3. Da Silva F. M., Gomes A. K., Jones J., Jr.: Can. J. Chem. 1999, 77, 624.
4. Tsukinoki T., Tsuzuki H.: Green Chem. 2001, 3, 37.
5. Tsukinoki T., Kanda T., Liu G.-B., Tsuzuki H., Tashiro M.: Tetrahedron Lett. 2000, 41, 5865.
6. Liu G.-B., Tsukinoki T., Kanda T., Mitoma Y., Tashiro M.: Tetrahedron Lett. 1998, 39, 5991.
7. Breton G. W., Hughey C. A.: J. Chem. Educ. 1998, 75, 85.
8. a) Sessler J. L., Weghorn S. J.: Expanded, Contracted & Isomeric Porphyrins. Pergamon Press, New York 1997;
9. b) Sessler J. L., Camiolo S., Gale P. A.: Coord. Chem. Rev. 2003, 240, 17;
10. c) Kadish K. M., Smith K. M., Guilard R.: The Porphyrin Handbook, Vol. 2. Academic Press, San Diego 2000;
11. d) Sessler J. L., Seidel D.: Angew. Chem., Int. Ed. 2003, 42, 5134.
12. Kadish K. M., Smith K. M., Guilard R. (Eds): The Porphyrin Handbook, Vol. 1. Academic Press, San Diego 2000.
13. a) Taniguchi R., Shimizu S., Suzuki M., Shin J.-Y., Furuta H., Osuka A.: Tetrahedron Lett. 2003, 44, 2505;
14. b) Shimizu S., Shin J.-Y., Furuta H., Ismael R., Osuka A.: Angew. Chem., Int. Ed. 2003, 42, 78;
15. c) Shin J.-Y., Furuta H., Yoza K., Igarashi S., Osuka A.: J. Am. Chem. Soc. 2001, 123, 7190;
16. d) Furuta H., Maeda H., Osuka A.: J. Org. Chem. 2000, 65, 4222.
17. a) Záruba K., Tománková Z., Charvátová J., Kavenová I., Bouř P., Matějka P., Fähnrich J., Volka K., Král V.: Anal. Chim. Acta 2001, 437, 39;
18. b) Sessler J. L., Král V., Genge J. W., Thomas R. E., Iverson B. L.: Anal. Chem. 1998, 70, 2516;
19. c) Sessler J. L., Genge J. W., Gale P. A., Král V.: Calixarenes for Separations (G. J. Lumetta, R. D. Rogers and A. S. Golapan, Eds). ACS Symp. Series, Austin 2000, 757, 238-254;
20. d) Volf R., Shishkanova T. V., Matějka P., Hamplová M., Král V.: Anal. Chim. Acta 1999, 381, 197;
21. e) Volf R., Shishkanova T. V., Král V.: J. Inclusion Phenom. Macrocycl. Chem. 1999, 35, 111.
22. a) Králová J., Dvořák M., Král V.: J. Med. Chem. 2003, 46, 2049;
23. b) Král V., Davis J., Andrievsky A., Králová J., Synytsa A., Poučková P., Sessler J. L.: J. Med. Chem. 2002, 45, 1073.
24. a) Rusin O., Král V.: J. Chem. Soc., Chem. Commun. 1999, 2367;
25. b) Král V., Sessler J. L., Shishkanova T. V., Gale P. G., Volf R.: J. Am. Chem. Soc. 1999, 121, 8771;
26. Sessler J. L., Král V., Shishkanova T. V., Gale P. A.: Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 4848;
27. Rusin O., Lang K., Kral V.: Chem. Eur. J. 2002, 8, 655.
28. Bruckner C., Sternberg E. D., Boyle R. W., Dolphin D.: Chem. Commun. 1997, 1689.
29. Furuta H., Maeda H., Osuka A.: Chem. Commun. 2002, 1795.
30. Ka J.-W., Lee C.-H.: Tetrahedron Lett. 2000, 41, 4609.
31. Lee Ch.-H., Lindsey J. S.: Tetrahedron 1994, 50, 11427.
32. Littler B. J., Miller M. A., Hung C.-H., Wagner R. W., O'Shea D. F., Boyle P. D., Lindsey J. S.: J. Org. Chem. 1999, 64, 1391.
33. Beck M. T., Rabai G.: Acta Chim. Hung. 1984, 117, 125.
34. Sobral A. J. F. N., Rebanda N. G. C. L., da Silva M., Lampreia S. H., Silva M. R., Beja A. M., Paixão J. A., Rocha Gonsalves A. M. d'A.: Tetrahedron Lett. 2003, 44, 3971.
35. 18).
36. a) Water solubility of benzaldehyde (1a) at 20°C is 3.3 g/l. Shcherbakova V. A., Laurinavichius K. S., Akimenko V. K.: Chemosphere 1999, 39, 1861;
37. b) Water solubility of 4-methoxybenzaldehyde (1d) at 18°C is 3.3 g/l. Haley M.: J. Chem. Soc. 1951, 3155.
38. Vigmond S. J., Kallury K. M. R., Thompson M.: Anal. Chem. 2002, 64, 2763.