Pictet-Spengler condensation reactions catalyzed by a recyclable H +-montmorillonite as a heterogeneous broønsted acid

Science China Chemistry

Volumn 53, Issue 3, 2010, Pages 562-568

  Wang, Yu Feng ^a   Song, Zhan Bo ^a   Chen, Chun Xia ^a   Peng, Jin Song ^a  

^a NORTHEAST FORESTRY UNIVERSITY   (China)

Author keywords

Catalyst recycling; Green synthesis; Heterogeneous catalysis; Mesoporous materials

Indexed keywords

C-C BOND FORMING REACTION; CARBOLINES; CATALYST RECYCLING; CATALYTIC ACTIVITY; CATALYTIC PERFORMANCE; ENVIRONMENTALLY FRIENDLY PROCESS; GREEN SYNTHESIS; HETEROGENEOUS CATALYSIS; MONTMORILLONITE CLAY; PHENYLETHYLAMINES; REUSABLE CATALYSTS; SOLVENT FREE CONDITIONS;

ALDEHYDES; CATALYSIS; CATALYST ACTIVITY; CLAY MINERALS; CONDENSATION; CONDENSATION REACTIONS; ORGANIC SOLVENTS; RECYCLING; SILICATE MINERALS; SYNTHESIS (CHEMICAL);

MESOPOROUS MATERIALS;

EID: 77950929834     PISSN: 16747291     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11426-010-0073-4     Document Type: Article

References (29)

1. Laszlo P. Chemical reactions on clays. Science, 1987, 235:1473-1477
2. Pinnavaia TJ. Intercalated clay catalysts. Science, 1983, 220:365-371
3. Rajender SV. Clay and clay-supported reagents in organic synthesis. Tetrahedron, 2002, 58:1235-1255
4. Kaneda K. Cation-exchanged montmorillonites as solid acid catalysts for organic synthesis. Synlett, 2007, 999-1015 (Pubitemid 46715891)
5. Kaneda K, Mori K, Mizugaki T, Ebitani K. Design of high-performance heterogeneous metal catalysts for green and sustainable chemistry. Bull Chem Soc Jpn, 2006, 79:981-1016 (Pubitemid 44681186)
6. Clark JH, Macquarrie DJ. Environmentally friendly catalytic methods. Chem Soc Rev, 1996, 25:303-310 (Pubitemid 127003476)
7. Pictet A, Spengler T. Über die bildung von isochinolin-derivaten durch einwirkung von methylal auf phenyl-äthylamin, phenyl-alanin und tyrosin. Ber Dtsch Chem Ges, 1911, 44:2030-2036
8. Cox ED, Cook J. The Pictet-Spengler condensation: a new direction for an old reaction. Chem Rev, 1995, 95:1797-1842
9. Nielsen TE, Diness F, Meldal M. The Pictet-Spengler reaction in solid-phase combinatorial chemistry. Curr Opin Drug Discovery Dev, 2003, 6:801-814 (Pubitemid 38084080)
10. Larghi EL, Amongero M, Bracca ABJ, Kauffman TS. The intermolecular pictet-spengler condensation with chiral carbonyl derivatives in the stereoselective syntheses of optically-active isoquinoline and indole alkaloids. ARKIVOC, 2005, xii: 98-153 (Pubitemid 41542711)
11. Royer J, Bonin M, Micouin L. Chiral heterocycles by iminium ion cyclization. Chem Rev, 2004, 104:2311-2352
12. Molina P, Fresneda PM, Zafra SG. An iminophosphorane-mediated efficient synthesis of the alkaloid eudistomin U of marine origin. Tetrahedron Lett, 1995, 36:3581-3582 (Pubitemid 24118879)
13. amethyl-16- epipericyclivine. J Org Chem, 2003, 68:7565-7581
14. 3. Bioorg Med Chem, 2005, 13:5154-5158 (Pubitemid 41039974)
15. Seayad J, Seayad AM, List B. Catalytic asymmetric Pictet-Spengler reaction. J Am Chem Soc, 2006, 128:1086-1087 (Pubitemid 43190615)
16. Taylar MS, Jacobsen EN. Highly enantioselective catalytic acyl-Pictet-Spengler reactions. J Am Chem Soc, 2004, 126:10558-10559 (Pubitemid 39129154)
17. Hegedus A, Hell Z. One-step preparation of 1-substituted tetrahydroisoquinolines via the Pictet-Spengler reaction using zeolite catalysts. Tetrahedron Lett, 2004, 45:8553-8555 (Pubitemid 39369913)
18. Saha B, Sharma S, Sawant D, Devesh S, Bijoy K. Water as an efficient medium for the synthesis of tetrahydro-p-carbolines via Pictet-Spengler reactions. Tetrahedron Lett, 2007, 48:1379-1383 (Pubitemid 46136406)
19. Saito A, Numaguchi J, Hanzawa Y. Pictet-Spengler reactions catalyzed by Brønsted acid-surfactant-combined catalyst in water or aqueous media. Tetrahedron Lett, 2007, 48:835-839 (Pubitemid 46027190)
20. Saito A, Takayama M, Yamazaki A, Numaguchi J, Hanzawa Y. Synthesis of tetrahydroisoquinolines and isochromans via Pictet-Spengler reactions catalyzed by Brønsted acid-surfactant combined catalyst in aqueous media. Tetrahedron, 2007, 63:4039-4047 (Pubitemid 46527726)
21. Saha B, Sharma S, Sawant D, Kundu B. Water as an efficient medium for the synthesis of tetrahydro-β-carbolines via Pictet-Spengler reactions. Tetrahedron Lett, 2007, 48:1379-1383 (Pubitemid 46136406)
22. In the progress of preparing this article, Török and Huang reported a bifunctional catalyst (Pd/C/K-10) for the one-pot microwave-assisted Pictet-Spengler cyclization/dehydrogenation reaction to afford β-carbolines. See: Kulkarni A, Abid M, Török B, Huang X. A direct synthesis of β-carbolines via a three-step one-pot domino approach with a bifunctional Pd/C/K-10 catalyst. Tetrahedron Lett, 2009, 50:1791-1794
23. Liu F, You Q. Microwave-assisted one-pot preparation of tetrahydro-ß-carboline hydrochlorides under solvent-free conditions. Syn Commun, 2007, 37:3933-3938 (Pubitemid 350145747)
24. Bikash P, Parasuraman J, Venkatachalam SG. Microwave assisted Pictet-Spengler and Bischler-Napieralski reactions. Syn Commun, 2003, 33, 2339-2348
25. A comprehensive review on C-C bond formation in aqueous medium: Li C. Organic reactions in aqueous media with a focus on carboncarbon bond formations: a decade update. Chem Rev, 2005, 105:3095-3166
26. Maryanoff BE, Zhang CH, Cohen JH, Turchi IJ, Maryanoff CA. Cyclizations of N-acyliminium ions. Chem Rev, 2004, 104:1431-1628
27. 2-expanded liquid media. In situ generation of carbamates as a strategy for reactions of amines in supercritical carbon dioxide. Chem Commun, 2005, 4465-4467 (Pubitemid 41375037)
28. Jiang W, Sui Z, Chen X. Synthesis of optically pure pyrroloquinolones via Pictet-Spengler and Winterfeldt reactions. Tetrahedron Lett, 2002, 43:8941-8945 (Pubitemid 35335680)
29. Adams JM, Clement DE, Graham SH. Reactions of alcohols with alkenes over an aluminum-exchanged montmorillonite. Clay Clay Miner, 1983, 3:129-136