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Synthesis 2010(2): 249-254
DOI: 10.1055/s-0029-1217108
DOI: 10.1055/s-0029-1217108
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
An Expedient Three-Component Synthesis of Tertiary Benzylamines
Further Information
Received
9 July 2009
Publication Date:
06 November 2009 (online)
Publication History
Publication Date:
06 November 2009 (online)
Abstract
A Mannich-like zinc-mediated three-component reaction of aromatic halides, amines, and paraformaldehyde is described. This procedure, which involves the in situ formation of arylzinc reagents, allows the straightforward synthesis of a range of functionalized tertiary benzylamines.
Key words
multicomponent reactions - amines - catalysis - zinc - organometallic reagents
-
1a
Kise N.Ozaki H.Terui H.Ohya K.Ueda N. Tetrahedron Lett. 2001, 42: 7637 -
1b
Cecchetto A.Minisci F.Recupero F.Fontanab F.Pedullic GF. Tetrahedron Lett. 2002, 43: 3605 -
2a
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 -
2b
Castellano S.La Colla P.Musiu C.Stefancich G. Arch. Pharm. (Weinheim, Ger.) 2000, 333: 162 -
2c
Nussbaumer P.Dorfstaetter G.Grassberger MA.Leitner I.Meingassner JG.Thirring K.Stuetz A. J. Med. Chem. 1993, 36: 2115 -
2d
Hagihara K.Nishiya Y.Kurihara A.Kazui M.Farid NA.Ikeda T. Drug Metab. Pharmacokinet. 2008, 23: 412 -
2e
Altomare C.Summo L.Cellamare S.Varlamov AV.Voskressensky LG.Borisova TN.Carotti A. Bioorg. Med. Chem. Lett. 2000, 10: 581 -
2f
Gooding OW.Beard CC. Heterocycles 1991, 32: 1777 -
3a
Abdel-Magid AF.Carson KG.Harris BD.Maryanoff CA. J. Org. Chem. 1996, 61: 3849 -
3b
Apodaca R.Xiao W. Org. Lett. 2001, 3: 1745 -
3c
Kumpaty HJ.Bhattacharyya S. Synthesis 2005, 2205 -
4a
Hazari N.Mountford P. Acc. Chem. Res. 2005, 38: 839 -
4b
Hultzsch KC. Adv. Synth. Catal. 2005, 347: 367 -
4c
Hultzsch KC. Org. Biomol. Chem. 2005, 3: 1819 -
4d
Xu LW.Xia CG. Eur. J. Org. Chem. 2005, 633 -
4e
Hong S.Marks TJ. Acc. Chem. Res. 2004, 37: 673 -
4f
Beller M.Tillack A.Seayad J. In Transition Metals for Organic Synthesis 2nd ed., Vol. 2:Beller M.Bolm C. VCH; Weinheim: 2004. p.403-414 -
4g
Nobis M.Drieben-Hölscher B. Angew. Chem. Int. Ed. 2001, 40: 3983 -
4h
Ricci A. In Modern Amination Methods Wiley-VCH; Weinheim: 2000. -
4i
Müller T.Beller M. Chem. Rev. 1998, 98: 675 -
5a
The Chemistry of the Cyano Group
Rappoport Z. Interscience; London: 1970. -
5b
Houben-Weyl
4th
ed., Vol. E5:
Grundmann C. Thieme; Stuttgart: 1985. p.1313-1441 - For the amination of alcohols by an oxidation-imine formation-reduction process, see:
-
6a
Blackburn L.Taylor RJK. Org. Lett. 2001, 3: 1637 - For the amination of alcohols using phosphonium salts and Mitsunobu reactions, see:
-
6b
Zaragoza F.Stephensen H. J. Org. Chem. 2001, 66: 2518 -
6c
Nikam S. S.Kornberg B. E.Rafferty M. F. J. Org. Chem. 1997, 62: 3754 -
6d
Zaragoza F.Stephensen H. Tetrahedron Lett. 2000, 41: 1841 - For the ruthenium-catalyzed amination of alcohols, see:
-
6e
Hamid MHSA.Allen CL.Lamb GW.Maxwell AC.Maytum HC.Watson AJA.Williams JMJ. J. Am. Chem. Soc. 2009, 131: 1766 - For some recent examples of nucleophilic substitutions of halides by amines, see:
-
7a
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 -
7b
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 GA.Gormisky PE.Sandrock DL. 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 NA. In Multicomponent ReactionsZhu J.Bienaymé H. Wiley-VCH; Weinheim: 2005. p.199-223 ; however, to the best of our knowledge, no paper has been published in this field so far -
11a
Le Gall E.Troupel M.Nédélec J.-Y. Tetrahedron Lett. 2006, 47: 2497 -
11b
Le Gall E.Troupel M.Nédélec J.-Y. Tetrahedron 2006, 62: 9953 -
11c
Sengmany S.Le Gall E.Le Jean C.Troupel M.Nédélec J.-Y. Tetrahedron 2007, 63: 3672 -
11d
Haurena C.Sengmany S.Huguen P.Le Gall E.Martens T.Troupel M. Tetrahedron Lett. 2008, 49: 7121 - 12
Sengmany S.Le Gall E.Troupel M. Synlett 2008, 1031 - The synthesis of arylzinc reagents has been described starting from aryl bromides by using a cobalt-catalyzed process, see:
-
13a
Fillon H.Gosmini C.Périchon J. J. Am. Chem. Soc. 2003, 125: 3867 -
13b
Kazmierski I.Gosmini C.Paris J.-M.Périchon J. Tetrahedron Lett. 2003, 44: 6417 -
13c
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
Scotto di Tella AM.Dessaigne S.Boyer E.Maldonado J.Ghemri H. Eur. J. Med. Chem. 1984, 19: 131 - 16
Schnatterer S,Maier M,Petry F,Knauf W, andSeeger K. inventors; US 2009,082,389. - 17
Fujita K.Fujii T.Komatsubara A.Enoki Y.Yamaguchi R. Heterocycles 2007, 74: 673 - 18
Zhang M.Flynn DL.Hanson PR. 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