An expedient three-component synthesis of tertiary benzylamines

Synthesis

Volumn , Issue 2, 2010, Pages 249-254

  Le Gall, Erwan ^a   Decompte, Alexandre ^a   Martens, Thierry ^a   Troupel, Michel ^a  

^a CNRS Université Paris Est Créteil Val de Marne   (France)

Author keywords

Amines; Catalysis; Multicomponent reactions; Organometallic reagents; Zinc

Indexed keywords

AROMATIC HALIDE; ARYLZINC REAGENTS; BENZYLAMINES; FUNCTIONALIZED; IN-SITU FORMATIONS; MULTI-COMPONENT REACTIONS; ORGANOMETALLIC REAGENT; ORGANOMETALLIC REAGENTS; PARAFORMALDEHYDES; THREE COMPONENT REACTIONS; THREE-COMPONENT;

ACETAL RESINS; AMINES; CATALYSIS; ORGANOMETALLICS; ZINC;

SYNTHESIS (CHEMICAL);

AMINE; AROMATIC COMPOUND; BENZYLAMINE DERIVATIVE; HALIDE; PARAFORMALDEHYDE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; ZINC DERIVATIVE;

ARTICLE; CATALYSIS; CROSS COUPLING REACTION; HEATING; MANNICH REACTION; REACTION TIME; SYNTHESIS;

EID: 73949139053     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0029-1217108     Document Type: Article

References (20)

1. Kise N, Ozaki H, Terui H, Ohya K, Ueda N, Tetrahedron Lett. 2001 42 7637, Cecchetto A, Minisci F, Recupero F, Fontanab F, Pedullic G F., Tetrahedron Lett. 2002 43 3605
2. Miyazaki Y, Kato Y, Manabe T, Shimada H, Mizuno M, Egusa T, Ohkouchi M, Shiromizu I, Matsusue T, Yamamoto I, Bioorg. Med. Chem. Lett. 2006 16 2986, Castellano S, LaColla P, Musiu C, Stefancich G, Arch. Pharm. (Weinheim, Ger.) 2000 333 162, Nussbaumer P, Dorfstaetter G, Grassberger M A., Leitner I, Meingassner J G., Thirring K, Stuetz A, J.Med. Chem. 1993 36 2115, Hagihara K, Nishiya Y, Kurihara A, Kazui M, Farid N A., Ikeda T, Drug Metab. Pharmacokinet. 2008 23 412, Altomare C, Summo L, Cellamare S, Varlamov A V., Voskressensky L G., Borisova T N., Carotti A, Bioorg. Med. Chem. Lett. 2000 10 581, Gooding O W., Beard C C., Heterocycles 1991 32 1777
3. Abdel-Magid A F., Carson K G., Harris B D., Maryanoff C A., J. Org. Chem. 1996 61 3849, Apodaca R, Xiao W, Org. Lett. 2001 3 1745, Kumpaty H J., Bhattacharyya S, Synthesis 2005 2205
4. Hazari N, Mountford P, Acc. Chem. Res. 2005 38 839, Hultzsch K C., Adv. Synth. Catal. 2005 347 367, Hultzsch K C., Org. Biomol. Chem. 2005 3 1819, Xu L W., Xia C G., Eur. J. Org. Chem. 2005 633, Hong S, Marks T J., Acc. Chem. Res. 2004 37 673, Beller M, Tillack A, Seayad J, In Transition Metals for Organic Synthesis 2nd ed., Vol. 2, Beller M, Bolm C, VCH Weinheim 2004 403-414, Nobis M, Drieben-Hölscher B, Angew. Chem. Int. Ed. 2001 40 3983, Ricci A, In Modern Amination Methods Wiley-VCH Weinheim 2000, Müller T, Beller M, Chem. Rev. 1998 98 675
5. The Chemistry of the Cyano Group, Rappoport Z, Interscience London 1970 Houben-Weyl 4th ed., Vol. E5, Grundmann C, Thieme Stuttgart 1985 1313-1441
6. For the amination of alcohols by an oxidation-imine formation-reduction process, see:, Blackburn L, Taylor R J. K., Org. Lett. 2001 3 1637 For the amination of alcohols using phosphonium salts and Mitsunobu reactions, see:, Zaragoza F, Stephensen H, J. Org. Chem. 2001 66 2518, Nikam S. S, Kornberg B. E, Rafferty M. F, J. Org. Chem. 1997 62 3754, Zaragoza F, Stephensen H, Tetrahedron Lett. 2000 41 1841 For the ruthenium-catalyzed amination of alcohols, see:, Hamid M H. S. A., Allen C L., Lamb G W., Maxwell A C., Maytum H C., Watson A J. A., Williams J M. J., J. Am. Chem. Soc. 2009 131 1766
7. For some recent examples of nucleophilic substitutions of halides by amines, see:, Sheng R, Xu Y, Hu C, Zhang J, Lin X, Li J, Yang B, He Q, Hu Y, Eur. J. Med. Chem. 2009 44 7, Sato I, Morihira K, Inami H, Kubota H, Morokata T, Suzuki K, Hamada N, Iura Y, Nitta A, Imaoka T, Takahashi T, Takeuchi M, Ohta M, Tsukamoto S, Bioorg. Med. Chem. 2008 16 144
8. Molander G A., Gormisky P E., Sandrock D L., J. Org. Chem. 2008 73 2052
9. Nishiwaki K, Ogawa T, Shigeta K, Takahashib K, Matsuo K, Tetrahedron 2006 62 7034
10. The possible formation of benzylamines using Petasis multicomponent reaction has been mentioned, see:, Petasis N A., In Multicomponent Reactions, Zhu J, Bienaymé H, Wiley-VCH Weinheim 2005 199-223; however, to the best of our knowledge, no paper has been published in this field so far
11. LeGall E, Troupel M, Nédélec J.-Y, Tetrahedron Lett. 2006 47 2497, LeGall E, Troupel M, Nédélec J.-Y, Tetrahedron 2006 62 9953, Sengmany S, LeGall E, LeJean C, Troupel M, Nédélec J.-Y, Tetrahedron 2007 63 3672, Haurena C, Sengmany S, Huguen P, LeGall E, Martens T, Troupel M, Tetrahedron Lett. 2008 49 7121
12. Sengmany S, LeGall E, Troupel M, Synlett 2008 1031
13. The synthesis of arylzinc reagents has been described starting from aryl bromides by using a cobalt-catalyzed process, see:, Fillon H, Gosmini C, Périchon J, J. Am. Chem. Soc. 2003 125 3867, Kazmierski I, Gosmini C, Paris J.-M, Périchon J, Tetrahedron Lett. 2003 44 6417, Gosmini C, Amatore M, Claudel S, Périchon J, Synlett 2005 2171
14. An excess of the organozinc compound is required in order to trap water, which is formally evolved during the course of the reaction
15. ScottodiTella A M., Dessaigne S, Boyer E, Maldonado J, Ghemri H, Eur. J. Med. Chem. 1984 19 131
16. Schnatterer S, Maier M, Petry F, Knauf W, Seeger K, US 2009,082,389 2009
17. Fujita K, Fujii T, Komatsubara A, Enoki Y, Yamaguchi R, Heterocycles 2007 74 673
18. Zhang M, Flynn D L., Hanson P R., J. Org. Chem. 2007 72 3194
19. Kuboa T, Katoha C, Yamadaa K, Okanoa K, Tokuyamaa H, Fukuyamaa T, Tetrahedron 2008 64 11230
20. Iranpoor N, Firouzabadi H, Nowrouzi N, Khalili D, Tetrahedron 2009 65 3893