Copper-catalyzed multicomponent coupling/cycloisomerization reaction between substituted 1-formyl-9H-β-carbolines, secondary amines, and substituted alkynes for the synthesis of substituted 3-aminoindolizino[8,7-b] indoles

ACS Combinatorial Science

Volumn 14, Issue 12, 2012, Pages 665-672

  Dighe, Shashi U ^a   Hutait, Samiran ^a   Batra, Sanjay ^a  

^a CENTRAL DRUG RESEARCH INSTITUTE   (India)

Author keywords

carbolines; aminoindolizino 8,7 b indole; copper; multicomponent reaction

Indexed keywords

ALKYNE; AMINE; CARBOLINE DERIVATIVE; COPPER; INDOLE DERIVATIVE; INDOLIZINE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; STEREOISOMERISM; SYNTHESIS;

ALKYNES; AMINES; CARBOLINES; CATALYSIS; COPPER; CYCLIZATION; INDOLES; INDOLIZINES; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 84870947962     PISSN: 21568952     EISSN: None     Source Type: Journal    
DOI: 10.1021/co300123y     Document Type: Article

References (54)

1. Roll, D. M.; Ireland, C. M.; Lu, H. S. M.; Clardy, J. Fascaplysin, an unusual antimicrobial pigment from the marine sponge Fascaplysinopsis sp J. Org. Chem. 1988, 53, 3276-3278
2. Pelcman, B.; Gribble, G. W. Total synthesis of the marine sponge pigment fascaplysin Tetrahedron Lett. 1990, 31, 2381-2384 (Pubitemid 20146885)
3. Zhidkov, M. E.; Baranova, O. V.; Balaneva, N. N.; Fedorov, S. N.; Radchenko, O. S.; Dubovitskii, S. V. The first syntheses of 3-bromofascaplysin, 10-bromofascaplysin and 3,10-dibromofascaplysinî-̧marine alkaloids from Fascaplysinopsis reticulata and Didemnum sp. by application of a simple and effective approach to the pyrido[1,2- a:3,4- b ′]diindole system Tetrahedron Lett. 2007, 48, 7998-8000 (Pubitemid 47538714)
4. Segraves, N. L.; Robinson, S. J.; Garcia, D.; Said, S. A.; Fu, X.; Schmitz, F. J.; Pietraszkiewicz, H.; Valeriote, F. A.; Crews, P. Comparison of Fascaplysin and Related Alkaloids: A study of structures, cytotoxicities, and sources J. Nat. Prod. 2004, 67, 783-792 (Pubitemid 38702733)
5. Allin, S. M.; Gaskell, S. N.; Elsegooda, M. R. J.; Martin, W. P. A new asymmetric synthesis of the natural enantiomer of the indolizidino[8,7- b ]indole alkaloid (+)-harmicine Tetrahedron Lett. 2007, 48, 5669-5671 (Pubitemid 47044887)
6. Knolker, H.-J.; Agarwal, S. Novel Three-Step Synthesis of (±)-Harmicine Synlett 2004, 1767-1768
7. Kam, T.-S.; Sim, K.-M. Alkaloids from Kopsia griffithii Phytochemistry 1998, 47, 145-147 (Pubitemid 28138677)
8. Saha, S.; Reddy, Ch. V. R.; Patro, B. Facile two-step synthesis of crispine A and harmicine by cyclopropylimine rearrangement Tetrahedron Lett. 2011, 52, 4014-4016
9. Kirsch, G.; Konig, G. M.; Wright, A. D.; Kaminsky, R. A New Bioactive Sesterterpene and Antiplasmodial Alkaloids from the Marine Sponge Hyrtios cf. erecta J. Nat. Prod. 2000, 63, 825-829 (Pubitemid 30452181)
10. Charan, R. D.; McKee, T. C.; Gustafson, K. R.; Pannell, L. K.; Boyd, M. R. Thorectandramine, a novel Β-carboline alkaloid from the marine sponge Thorectandra sp Tetrahedron Lett. 2002, 43, 5201-5204 (Pubitemid 34686902)
11. Popov, A. M.; Stonik, V. A. Physiological activity of fascaplysin, an unusual pigment from tropic sea sponges Antibiot. Khimioter. 1991, 36, 12-14
12. Chem. Abstr. 1991, 114, 220919u.
13. Hormann, A.; Chaudhuri, B.; Fretz, H. DNA binding properties of the marine sponge pigment fascaplysin Bioorg. Med. Chem. 2001, 9, 917-921 (Pubitemid 32448111)
14. Herbert, D. R. Pharmacologically active indolizino[8,7- b ]indoles and related compounds. German Patent 2,033,631, 1971
15. Chem. Abstr. 1972, 76, 113061h.
16. Herbert, D. R.; Smith, H. Azonino[5,4- b ]indole and 3 H -azepino[5,4- b ]indole, and 3 H -indolizino[8,7- b ]indole derivatives as diuretics. German Patent 2,004,356, 1971
17. Chem. Abstr. 1971, 75, 118297d.
18. Wenkert, E.; Garratt, S.; Dave, K. G. A quebrachamine model Can. J. Chem. 1964, 42, 489-490
19. Kutney, J. P.; Abdurahman, N.; Gletsos, C.; Le Quesne, P.; Piers, E.; Vlattas, I. Total synthesis of indole and dihydroindole alkaloids. V. Total synthesis of dl-quebrachamine and dl-aspidospermidine. General entry into the aspidosperma alkaloids J. Am. Chem. Soc. 1970, 92, 1727-1735
20. Jida, M.; Soueidan, O.-M.; Deprez, B.; Lacondea, G.; Deprez-Poulain, R. Racemic and diastereoselective construction of indole alkaloids under solvent and catalyst-free microwave assisted Pictet Spengler condensation Green Chem. 2012, 14, 909-911
21. Nurmaganbetov, Z. S.; Shultz, E. E.; Chernov, S. V.; Turmukhambetov, A. Z.; Seydakhmetova, R. B.; Shakirov, M. M.; Tolstikov, G. A.; Adekenov, S. M. Synthesis of substituted indolizino[8,7- b ]indoles from harmine and their biological activity Chem. Heterocycl. Compd. 2011, 46, 1494-1499 (Translated from Khim. Geterotsikl. Soedinenii 2010, 12, 1849â"1856
22. Waldmann, H.; Eberhardt, L.; Wittstein, K.; Kumar, K. Silver catalyzed cascade synthesis of alkaloid ring systems: concise total synthesis of fascaplysin, homofascaplysin C and analogues Chem. Commun. 2010, 46, 4622-4624
23. Poissonnet, G.; Théret-Bettiol, M.-H.; Dodd, R. H. Preparation and 1,3-Dipolar Cycloaddition Reactions of Β-Carboline Azomethine Ylides: A Direct Entry into C-1- and/or C-2-Functionalized Indolizino[8,7- b ]indole Derivatives J. Org. Chem. 1996, 61, 2273-2282 (Pubitemid 26139828)
24. Narayan, K.; Cook, J. M. Carboxyl-mediated Pictet-Spengler reaction. Improved synthesis of 2,3,5,6,11,11 b -hexahydro-3-oxo-1 H -indolizino[8,7- b ]indoles from tryptamine-2-carboxylic acids J. Org. Chem. 1991, 56, 5733-5736
25. Hershenson, F. M. Synthesis of ring-fused pyrroles. 1,3-Dipolar cycloaddition reactions of munchnone derivatives obtained from tetrahydro-Β-carboline-3- and -1-carboxylic acids J. Org. Chem. 1972, 37, 3111-3113
26. Singh, V.; Hutait, S.; Batra, S. Advancing the Moritaâ" Baylisâ"Hillman Chemistry of 1-formyl-Β-carbolines for the synthesis of Indolizino-indole Derivatives Eur. J. Org. Chem. 2010, 3684-3691
27. Chandrashekhar, N. K.; Karvekar, M. D.; Das, A. K. Synthesis and Antioxidant Activity of 1,2-Bis(1-ethyl-2-substitutedphenylindolizin-3-yl) diselane Asian J. Chem. 2008, 20, 6183-6188
28. Weide, T.; Arve, L.; Prinz, H.; Waldmann, H.; Kessler, H. 3-Substituted indolizine-1-carbonitrile derivatives as phosphatase inhibitors Bioorg. Med. Chem. Lett. 2006, 16, 59-63 (Pubitemid 41625641)
29. Gladsy, J.; Kumar, D. A. Orient. J. Chem. 2006, 22, 427-430
30. Michael, J. P. Simple indolizidine and quinolizidine alkaloids. In The Alkaloids, Chemistry and Pharmacology; Cordell, G., Ed.; Academic Press: New York, 2001; pp 91-258. (Pubitemid 33805320)
31. Micheal, J. P. Indolizidine and quinolizidine alkaloids Nat. Prod. Rep. 2002, 19, 719-741
32. Gupta, S. P.; Mathur, A. N.; Nagappa, A. N.; Kumar, D.; Kumaran, S. A quantitative structureâ"activity relationship study on a novel class of calcium-entry blockers: 1-[{4-(aminoalkoxy)phenyl}sulphonyl]indolizines Eur. J. Med. Chem. 2003, 38, 867-873 (Pubitemid 37311400)
33. Sonnet, P.; Dallemagne, P.; Guillon, J.; Enguehard, C.; Stiebing, S.; Tanguy, J.; Bureau, R.; Rault, S.; Auvray, P.; Moslemi, S.; Sourdaine, P.; Séralini, G.-E. New aromatase inhibitors. Synthesis and biological activity of aryl-substituted pyrrolizine and indolizine derivatives Bioorg. Med. Chem. 2000, 8, 945-955 (Pubitemid 30336391)
34. Ostby, O. B.; Dalhus, B.; Gundersen, L.-L.; Rise, F.; Bast, A.; Haenen, G. R. M. M. Synthesis of 1-Substituted 7-Cyano-2,3-diphenylindolizines and Evaluation of Antioxidant Properties Eur. J. Org. Chem. 2000, 3763-3770
35. Gubin, J.; Lucchetti, J.; Mahaux, J.; Nisato, D.; Rosseels, G.; Clinet, M.; Polster, P.; Chatelain, P. A novel class of calcium-entry blockers: the 1-[[4-(aminoalkoxy)phenyl]sulfonyl]indolizines J. Med. Chem. 1992, 35, 981-988
36. Gubin, J.; de Vogelaer, H.; Inion, H.; Houben, C.; Lucchetti, J.; Mahaux, J.; Rosseels, G.; Peiren, M.; Clinet, M. Novel heterocyclic analogs of the new potent class of calcium entry blockers: 1-[[4-(aminoalkoxy)phenyl]sulfonyl] indolizines J. Med. Chem. 1993, 36, 1425-1433 (Pubitemid 23164499)
37. Taguchi, T. Organic electroluminiscent material containing nitrogen heterocyclic compounds as hole-transporting material for electroluminiscent devise for electroluminiscent display. JP 172280 Chem. Abstr. 2001, 135, 68647c
38. Taguchi, T. Novel indolizine compounds, production process for novel indolizine compounds, organic light-emitting device material having indolizine skeleton, and organic light-emitting device using these. U.S. Patent 15614, 2001
39. Chem. Abstr. 2001, 135, 202731f.
40. Yan, B.; Liu, Y. Gold-Catalyzed Multicomponent Synthesis of Aminoindolizines from Aldehydes, Amines, and Alkynes under Solvent-Free Conditions or in Water Org. Lett. 2007, 9, 4323-4326
41. Bai, Y.; Zeng, J.; Ma, J.; Liu, W.; Gorityala, B. K.; Liu, X.-W. Quick Access to Druglike Heterocycles: Facile Silver-Catalyzed One-Pot Multicomponent Synthesis of Aminoindolizines J. Comb. Chem. 2010, 12, 696-699
42. 3/TBAOH-Catalyzed Sequential Cross-Couplingâ"Cycloisomerization Reactions Synlett 2011, 2379-2383
43. Li, C.-J.; Wei, C. Highly efficient Grignard-type imine additions via Câ"H activation in water and under solvent-free conditions Chem. Commun. 2002, 268-269 (Pubitemid 34146482)
44. Wei, C.; Li, C.-J. J. Am. Chem. Soc. 2002, 124, 5638-5639
45. Wei, C.; Li, C.-J. Enantioselective Direct-Addition of Terminal Alkynes to Imines Catalyzed by Copper(I)pybox Complex in Water and in Toluene J. Am. Chem. Soc. 2003, 125, 9584-9585
46. Yan, B.; Zhou, Y.; Zhang, H.; Chen, J.; Liu, Y. Highly Efficient Sy nth esis of Functionalized Indolizines and Indolizinones by Coppe r-Catalyze d Cycloisomerizations of Propargylic Pyridines J. Org. Chem. 2007, 72, 7783-7786 (Pubitemid 47501652)
47. Liu, Y.; Wan, J.-P. Tandem reactions initiated by copper-catalyzed cross-coupling: A new strategy towards heterocycle synthesis Org. Biomol. Chem. 2011, 9, 6873-6894
48. Kelâin, A. V.; Sromek, A. W.; Gevorgyan, V. A Novel Cu-Assisted cycloisomerization of alkynyl imines: Efficient synthesis of Pyrroles and Pyrrole-containing Heterocycles J. Am. Chem. Soc. 2001, 123, 2074-2075 (Pubitemid 32200036)
49. 2-symmetrical cyclic amines were efficiently synthesized from the corresponding diols obtained from an enantioselective borohydride reduction of diketones in the presence of a chiral Β-ketoiminato cobalt(II) catalyst Synthesis 2004, 1434-1438
50. Cheng, C.; Sun, J.; Xing, L.; Xu, J.; Wang, X.; Hu, Y. A synergistic catalytic system based on Pd-C in the presence of 1,1,2-trichloroethane enabled the N -debenzylation of benzylamines to yield crystal amine hydrochlorides in practically quantitative yields J. Org. Chem. 2009, 74, 5671-5674
51. Hydrogenation on a Parr assembly in the presence of 10% Pd-C at 40 psi under methanol as medium resulted in a mixture of products.
52. Suzuki, H.; Tsukuda, A.; Kondo, M.; Aizawa, M.; Senoo, Y.; Nakajima, M.; Watanabe, T.; Yokoyama, Y.; Murakami, Y. Unexpected Debenzylation of N-Benzylindoles with Lithium Base. A New Method of N-Debenzylation Tetrahedron Lett. 1995, 36, 1671-1672
53. Suzuki, H.; Iwata, C.; Sakurai, K.; Tokumoto, K.; Takahashi, H.; Hanada, M.; Yokoyama, Y.; Murakami, Y. General Synthetic Route for l-Substituted 4-Oxygenated Β-Carbolines Tetrahedron Lett. 1997, 53, 1593-1606
54. Haddach, A. A.; Kelleman., A.; Deaton-Rewolinski, M. V. An efficient method for the N -debenzylation of aromatic heterocycles Tetrahedron Lett. 2002, 43, 399-402 (Pubitemid 34037910)