Remarkable iodine-catalyzed synthesis of novel pyrrole- bearing n-polyaromatic β-lactams

Molecules

Volumn 15, Issue 2, 2010, Pages 1082-1088

  Bandyopadhyay, Debasish ^a   Rivera, Gildardo ^a   Salinas, Isabel ^a   Aguilar, Hector ^a   Banik, Bimal K ^a  

^a UNIVERSITY OF TEXAS PAN AMERICAN   (United States)

Author keywords

lactams; Catalysis; Iodine; Pyrroles

Indexed keywords

AROMATIC HYDROCARBON; BETA LACTAM; IODINE; PYRROLE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMISTRY; SYNTHESIS;

BETA-LACTAMS; CATALYSIS; HYDROCARBONS, AROMATIC; IODINE; PYRROLES;

EID: 77649198462     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules15021082     Document Type: Article

References (33)

1. Lainton, J.A.H.; Hoffman, J.W.; Martin, D.R.; Compton, D.R. 1-Alkyl-3-(1-naphthoyl)pyrroles: A new class of cannabinoid. Tetrahedron Lett. 1995, 36, 1401-1404.
2. De Leon, C.Y.; Ganem, B. A new approach to porphobilinogen and its analogs. Tetrahedron 1997, 53, 7731-7752.
3. Gilchrist, T.L. Synthesis of aromatic heterocycles. J. Chem. Soc. Perkin Trans 1 1998, 615-628 and references cited therein.
4. Dieter, R.K.; Yu, H. A facile synthesis of polysubstituted pyrroles. Org. Lett. 2000, 2, 2283-2286.
5. Iwasawa, N.; Maeyama, K.; Saitou, M. Reactions of propargyl metallic species generated by the addition of alkynyllithiums to fischer-type carbene complexes. J. Am. Chem. Soc. 1997, 119, 1486-1487.
6. Furstner, A.; Weintritt, H.; Hupperts, A. A new, titanium-mediated approach to pyrroles: First synthesis of lukianol a and lamellarin-o-dimethyl ether. J. Org. Chem. 1995, 60, 6637-6641.
7. 2N: Synthon. J. Org. Chem. 1994, 59, 4551-4555.
8. Arcadi, A.; Rossi, E. Synthesis of functionalized furans and pyrroles through annulation reactions of 4-pentynones. Tetrahedron 1998, 54, 15253-15272.
9. 4/Et3N. J. Org. Chem. 1999, 64, 4204-4205 and references cited therein.
10. Cooney J.V.; McEwen, W.E. Synthesis of substituted pyrroles by intramolecular condensation of a Wittig reagent with the carbonyl group of a tertiary amide. J. Org. Chem. 1981, 46, 2570-2573.
11. Ruault, P.; Pilard, J-F.; Touaux, B.; Boullet, F.T.; Hamelin, J. Rapid generation of amines by microwave irradiation of ureas dispersed on clay. Synlett 1994, 935-936.
12. Danks, T.N. Microwave assisted synthesis of pyrroles. Tetrahedron Lett. 1999, 40, 3957-3960.
13. Becker, F.F.; Banik, B.K. Polycyclic aromatic compounds as anticancer agents: Synthesis and biological evaluation of some chrysene derivatives. Bioorg. Med. Chem. Lett. 1998, 8, 2877-2880.
14. Becker, F.F.; Mukhopadhyay, C.; Hackfeld, L.; Banik, I.; Banik, B.K. Polycyclic aromatic compounds as anticancer agents: Synthesis and biological evaluation of dibenzofluorene derivatives. Bioorg. Med. Chem. 2000, 8, 2693-2699.
15. Banik, B.K.; Becker, F.F. Polycyclic aromatic compounds as anticancer agents. 4. Structureactivity relationships of chrysene and pyrene derivatives. Bioorg. Med. Chem. 2001, 9, 593-605.
16. Banik, B.K.; Becker, F.F. Synthesis, electrophilic substitution and structure-activity relationship studies of polycyclic aromatic compounds towards the development of anticancer agents. Curr. Med. Chem. 2001, 8, 1513-1533.
17. Banik, I.; Becker, F.F.; Banik, B.K. Stereoselective synthesis of β-lactams with polyaromatic imines: Entry to new and novel anticancer agents. J. Med. Chem. 2003, 46, 12-15.
18. Banik, B.K.; Suhendra, M.; Banik, I.; Becker, F.F. Indium/ammonium chloride mediated selective reduction of aromatic nitro compounds: Practical synthesis of 6-aminochrysene. Synth. Commun. 2000, 30, 3745-3754.
19. Banik, B.K.; Banik, I.; Hackfeld, L.; Becker, F.F. Indium-mediated reductive cyclizations in aqueous ethanol: highly efficient synthesis of heterocyclic compounds of biological interest. Heterocycles 2002, 56, 467-470.
20. Banik, B.K.; Hackfeld, L.; Becker, F.F. Studies on the indium-mediated reduction of imines. Synth. Commun. 2001, 31, 1581-1586.
21. Samajdar, S.; Becker, F.F.; Banik, B.K. Surface-mediated highly efficient oxidation of alcohols by bismuth nitrate. Synth. Commun. 2001, 31, 2691-2695.
22. Banik, B.K.; Mukhopadhyay, C.; Becker, F.F. An expeditious one pot synthesis of dibenzo[a,g]fluorene. Synth. Commun. 2001, 31, 2399-2403.
23. Dasgupta, S.K.; Banik, B.K. A new entry to N-unsubstituted β-lactams through a solid-phase approach. Tetrahedron Lett. 2002, 43, 9445-9447.
24. Banik, B.K.; Samajdar, S.; Banik, I. A facile synthesis of oxazines by indium-induced reductionrearrangement of the nitro β-lactams. Tetrahedron Lett. 2003, 44, 1699-1701.
25. Srivastava, N.; Banik, B.K. Bismuth nitrate-catalyzed versatile Michael reactions. J. Org. Chem. 2003, 68, 2109-2114.
26. Banik, B.K.; Manhas, M.S.; Bose, A.K. Stereospecific glycosylation via ferrier rearrangement for optical resolution. J. Org. Chem. 1994, 59, 4714-4716.
27. Banik, B.K.; Manhas, M.S.; Bose, A.K. Studies on lactams. 103. Enantiopure a-hydroxy-β- lactams via stereoselective glycosylation. Tetrahedron Lett. 1997, 38, 5077-5080.
28. Banik, B.K.; Zegrocka, O. Manhas, M.S.; Bose, A.K. Studies on lactams. 104. Enantiomerically pure β-lactams with the thienamycin side chain via glycosylation. Heterocycles 1997, 27, 173-176.
29. Banik, B.K.; Fernandez, M.; Alvarez, C. Iodine-catalyzed highly efficient Michael reaction of indoles under solvent-free condition. Tetrahedron Lett. 2005, 46, 2479-2482.
30. Banik, B.K.; Garcia, I.; Moarles, F.; Aguilar, C. Novel synthesis of substituted pyrrole bound to indolinone via molecular iodine-catalyzed reaction. Heterocycl. Commun. 2007, 13, 109-112.
31. Banik, B.K.; Garza, R. Molecular iodine-catalyzed deprotection of acetals and ketals in acetone. Chem. Edu. 2007, 12, 75-76.
32. Bandyopadhyay, D.; Xavier, M.; Banik, B.K. Highly stereoselective β-lactam synthesis via the Staudinger reaction using polyaromatic imines. Heterocycl. Commun. 2009, 15, 229-231.
33. Rivera, G.; Bandyopadhyay, D.; Jaggi, S.; Gonzales, R.C.; Banik, B.K. An expeditious synthesis of 3-amino β-lactams derived from polyaromatic compounds. Heterocycl. Commun. 2009, 15, 323-325.