Substituted pyrrolizine-bridged bipyrroles synthesis via ring annulation under green conditions

Document Type : Article

Authors

1 Department of Medical Nanotechnology, Applied Biophotonics Research Center, Science and Research Branch, Islamic Azad University, Tehran, Iran

2 Department of Chemistry, School of Sciences, Ferdowsi University of Mashhad, Mashhad, P.O. Box 91775-1436, Iran

10.24200/sci.2021.56153.4576

Abstract

Several new substituted 2,3-dihydro-1H-pyrrolizine-bridged bipyrroles were synthesized via ring annulation under green aqueous conditions. In this work, the acid-catalyzed condensation of the used diketones with pyrrole did not result in the formation of expected divergent bisdipyrromethanes. However, new important pyrrolizine-bridged bipyrroles were synthesized in good yields. Ferric hydrogensulfate was used as an environmentally friendly homogeneous acidic catalyst to produce pure products in aqueous conditions. This catalyst has enabled us to synthesize
pyrrolizine-bridged bipyrroles with bearing functional groups at designated positions. These synthesized compounds can be used for various unknown and known applications such as chiral catalysts and essential biological activities.

Keywords


References   1. Eshghi, H., Rahimizadeh, M., Attaran, N., et al.   Dipyrromethane as a new organic reagent for the   synthesis of gold nanoparticles: Preparation and application",   J. Iran. Chem. Soc., 10(6), pp. 1151{1157   (2013).   2. Ganesan, M., Lalonde, M.P., Gambarotta, S., et al.   Isolation and characterization of linear polymeric   f[1,1,-H10C6(_-C4H3N)2]2 Sm[Na(THF)]2gn: A 30-   Electron species with a (_5-Cp)4Ln type structure",   Organometallics, 20(12), pp. 2443{2445 (2001).   3. Gao, G., Korobkov, I., and Gambarotta, S. Divalent   molybdenum complexes of the dipyrrolide ligand system.   Isolation of a Mo2 unit with a 45_ twist angle",   Inorg. Chem., 43(3), pp. 1108{1115 (2004).   4. Gao, G.H., Lu, L., Gao, J.B., et al. One-step synthesis   of dipyrromethanes in the presence of ionic liquid   [Hmim]BF4", CHINESE Chem. Lett., 16(7), pp. 900{   902 (2005).   5. Mizutani, T., Erna, T., Tomita, T., et al. Design and   synthesis of a trifunctional chiral porphyrin with C2   symmetry as a chiral recognition host for amino acid   esters", J. Am. Chem. Soc., 116(10), pp. 4240{4250   (1994).   6. Vigmond, S.J., Ghaemmaghami, V., and Thompson,   M. Raman and resonance-Raman spectra of polypyrrole   with application to sensor{gas probe interactions",   Can. J. Chem., 73(10), pp. 1711{1718 (1995).   7. Lee, C.H. and S. Lindsey, J. One-ask synthesis of   meso-substituted dipyrromethanes and their application   in the synthesis of trans-substituted porphyrin   building blocks", Tetrahedron, 50(39), pp. 11427{   11440 (1994).   8. Casiraghi, G., Cornia, M., Rassu, G., et al. Synthesis   of porphyrin C-glycoconjugates", Nat. Prod. Lett.,   1(1), pp. 45{50 (1992).   9. Casiraghi, G., Cornia, M., Zanardi, F., et al. Synthesis   and characterization of porphyrin-sugar carbon   conjugates", J. Org. Chem., 59(7), pp. 1801{1808   (1994).   10. Hammel, D., Erk, P., Seliuler, B., et al. Synthesis and   reduction of 1,4-phenylene-bridged oligoporphyrins",   Adv. Mater., 4(11), pp. 737{739 (1992).   11. Chorghade, M., Dolphin, D., Dupre, D., et al. Improved   protocols for the synthesis and halogenation   of sterically hindered metalloporphyrins", Synthesis-   Stuttgart, 1996(11), pp. 1320{1324 (1996).   12. Naik, R., Joshi, P., Kaiwar, S.P., et al. Facile   synthesis of meso-substituted dipyrromethanes and   porphyrins using cation exchange resins", Tetrahedron,   59(13), pp. 2207{2213 (2003).   13. Salehi, P., Khodaei, M.M., Zol_gol, M.A., et al.   Catalytic Friedel-crafts acylation of alkoxy benzenes   by ferric hydrogensulfate", Synth. Commun., 33(8),   pp. 1367{1373 (2003).   14. Eshghi, H. Ferric hydrogensulfate catalysed Schmidt   reaction of ketones to amides under solvent-free conditions",   J. Chinese Chem. Soc., 53(4), pp. 987{990   (2006).   15. Samanta, R., Mahanta, S.P., Chaudhuri, S., et al.   New strapped calix[4]pyrrole based receptor for anions",   Inorganica Chim. Acta, 372(1), pp. 281{285   (2011).   16. Mahanta, S.P. and Panda, P.K. Unusual ring annulation   during condensation of acetylacetone with   pyrrole", Tetrahedron Lett., 50(8), pp. 890{892 (2009).   17. R_adl, S., _Cern_y, J., Klec_an, O., et al. A synthesis of   licofelone using Fenton's reagent", Tetrahedron Lett.,   49(36), pp. 5316{5318 (2008).   18. Sobral, A.J.F.N., Rebanda, N.G.C.L., Da Silva, M., et   al. One-step synthesis of dipyrromethanes in water",   Tetrahedron Lett., 44(20), pp. 3971{3973 (2003).