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Synthesis 2003(10): 1471-1499
DOI: 10.1055/s-2003-40507
DOI: 10.1055/s-2003-40507
REVIEW
© Georg Thieme Verlag Stuttgart ˙ New York
Recent Advances in Solution-Phase Multicomponent Methodology for the Synthesis of Heterocyclic Compounds
Further Information
Received
24 December 2002
Publication Date:
08 July 2003 (online)
Publication History
Publication Date:
08 July 2003 (online)
Abstract
Following the increased interest from the pharmaceutical industry for the generation of diverse libraries of heterocyclic compounds, scientific efforts have become more and more focused on the development of novel multi-component procedures as a means of gaining rapid access to such compounds. Initially, the development of solid-phase procedures received considerable attention. However, current efforts are increasingly concerned with the development of solution-phase procedures. The latter will be the subject of discussion in this review, which aims to give an overview of the progress made in the past decade.
After a general introduction, non-catalyzed, acid-catalyzed, and transition metal-catalyzed solution-phase multi-component procedures for the preparation of a wide range of heterocycles will be discussed. The last chapter discusses the role of cycloaddition reactions in the development of novel MCRs for the synthesis of heterocyclic compounds.
In spite of their important role in the synthesis of heterocyclic compounds, MCRs involving isocyanides are not discussed in this review, since the topic has been exhaustively reviewed several times.
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1Introduction
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2Non-Catalyzed MCRs
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3Acid-Catalyzed MCRs
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4Transition Metal-Catalyzed or -Mediated MCRs
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5MCRs Involving Cycloaddition Reactions
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6Conclusions and Outlook
Key words
heterocycles - multi-component reactions - combinatorial chemistry - parallel synthesis
- 1
Nicolaou KC.Vourloumis D.Winssinger N.Baran PS. Angew. Chem. Int. Ed. 2000, 39: 24 ; Angew. Chem. 2000, 112: 46 - 2
Wender PA.Handy ST.Wright DL. Chem. Ind. (London) 1997, 765 - 3
Hall N. Science 1994, 266: 32 -
4a
Passerini M. Gazz. Chim. Ital. 1921, 51: 121 -
4b
Passerini M. Gazz. Chim. Ital. 1921, 51: 181 -
4c
Ugi C. inventors; Steinbrückner DE-B 1,103,337. -
4d
Ugi C. Chem. Ber. 1961, 94: 734 -
4e
Ugi I.Dömling A.Hörl W. Endeavour 1994, 18: 115 - 5 For example see:
Tietze LF. Chem. Rev. 1996, 96: 115 - 6
Denmark SE.Thorarensen A. Chem. Rev. 1996, 96: 137 - 7
Dömling A.Ugi I. Angew. Chem. Int. Ed. 2000, 39: 3168 ; Angew. Chem. 2000, 112, 3300 - 8
Bienaymé H.Hulme CH.Oddon G.Schmitt P. Chem.-Eur. J. 2000, 6: 3321 - 9 For example see:
Bravo PA.Carrero MCP.Galan ER.Blazquez JAS. Heterocycles 2000, 1: 81 - 10 For example see:
Neuschutz K.Velker J.Neier R. Synthesis 1998, 3: 227 - 11 For example see:
Organ MG.Winkle DD.Huffman J. J. Org. Chem. 1997, 62: 5254 - 12 For example see:
Johnson WS.Gravestock MB.McCarry BE. J. Am. Chem. Soc. 1971, 93: 4332 - 13
Ranu BC.Hajra A. Tetrahedron 2001, 57: 4767 - 14
Weber L.Illgen K.Almstetter M. Synlett 1999, 366 - 15
Kitano Y.Chiba M.Tada M. Tetrahedron Lett. 1998, 39: 1911 - 16
Strecker S. Liebigs Ann. Chem. 1850, 27 - 17
Cotterill IC.Usyatinsky AY.Arnold JM.Clark DS.Dordick JS.Michels PC.Khmelnitsky YL. Tetrahedron Lett. 1998, 39: 1117 - 18
Hantzsch A. Ber. Dtsch. Chem. Ges. 1890, 23: 1474 -
19a
Biginelli P. Ber. Dtsch. Chem. Ges. 1891, 24: 1317 -
19b
Kappe CO. Acc. Chem. Res. 2000, 33: 879 -
19c
Kappe CO. Eur. J. Med. Chem. 2000, 35: 1043 -
19d
Dondoni A.Massi A.Sabbatini S. Tetrahedron Lett. 2002, 43: 5913 - 20
Robinson RJ. Chem. Soc. 1917, 762 - 21
Arend M.Westermann B.Risch N. Angew. Chem. Int. Ed. 1998, 37: 1044 ; Angew. Chem. 1998, 110, 1096 - 22
List B. Synlett 2001, 1675 -
23a
Bergs H. inventors; DE-B 566,094. -
23b
Bucherer T.Barsch H. J. Prakt. Chem. 1934, 140: 151 -
23c
Alonso F.Micó I.Nájera C.Sansano JM.Yus M.Ezquerra J.Yruretagoyena B.Gracia I. Tetrahedron 1995, 51: 10259 -
24a
Asinger F. Angew. Chem. 1958, 71: 67 -
24b
Dömling A.Ugi I. Tetrahedron 1993, 49: 9495 - 25
Dömling A.Bayler A.Ugi I. Tetrahedron 1995, 51: 755 - 26
Schlemminger I.Janknecht HH.Maison W.Saak W.Martens J. Tetrahedron Lett. 2000, 41: 7289 - 27
Bossio R.Marcos CF.Maracaccini S.Pepino R. Tetrahedron Lett. 1997, 38: 2519 - 28
Zhang JD.Jacobson A.Rusche JR.Herlihy W. J. Org. Chem. 1999, 64: 1074 - 29
Maracaccini S.Torroba T. Org. Prep. Proced. Int. 1993, 25: 141 - 30
Kobayashi S. Chem. Soc. Rev. 1999, 28: 1 - 31
Dax SL.McNally JJ.Youngman MA. Curr. Med. Chem. 1999, 6: 255 - 32
Sim MM.Ganesan A. J. Org. Chem. 1997, 62: 3230 - 33
Gewald K. Chem. Ber. 1965, 98: 3571 - 34
McKibben BP.Cartwright CH.Castelhano AL. Tetrahedron Lett. 1999, 40: 5471 - 35
Pinto IL.Jarvest RL.Serafinowska HT. Tetrahedron Lett. 2000, 41: 1597 - 36
Rajasekharan KN.Nair KP.Jenardanan GC. Synthesis 1986, 353 - 37
Hantzsch AR.Weber JH. Ber. Dtsch. Chem. Ges. 1887, 20: 3118 - 38
Masquelin TH.Obrecht D. Tetrahedron 2001, 57: 153 - 39
Singh SP.Parmar SS.Raman K.Stenberg VI. Chem. Rev. 1981, 81: 175 - 40
De Vries AHM.Hof RP.Staal D.Kellog RM.Feringa BL. Tetrahedron: Asymmetry 1997, 8: 1539 - 41
Strijtveen BM.Kellog RM. J. Org. Chem. 1986, 51: 3664 - 42
Holmes CP.Chinn JP.Look GC.Gordon EM.Gallop MA. J. Org. Chem. 1995, 60: 7328 - 43
Ware E. Chem. Rev. 1950, 46: 403 - 44
Hanessian S.Yang RY. Tetrahedron Lett. 1996, 37: 5835 - 45
Katritzky AR.Fali CN.Li J. J. Org. Chem. 1997, 62: 4148 - 46
Langer P.Döring M.Görls H. Eur. J. Org. Chem. 2001, 1511 - 47
Beckert R.Mayer R. Wiss. Z. Techn. Universität Dresden 1987, 2: 36 - 48
Naik SN.Pandey B.Ayyanger NR. Synth. Commun. 1988, 18: 625 -
49a
Zupancic JJ.Horn KA.Schuster GB. J. Am. Chem. Soc. 1980, 102: 5279 -
49b
Greene FD. J. Am. Chem. Soc. 1956, 78: 2250 - 50
Petasis NA.Akritopoulou I. Tetrahedron Lett. 1993, 34: 583 - 51
Petasis NA.Goodman A.Zavialov IA. Tetrahedron 1997, 53: 16463 - 52
Petasis NA.Zavialov IA. J. Am. Chem. Soc. 1998, 120: 11798 - 53
Petasis NA.Boral S. Tetrahedron Lett. 2001, 42: 539 - 54
Berrée F.Debache A.Marsac Y.Carboni B. Tetrahedron Lett. 2001, 42: 3591 - 55
Varma RS. Green Chem. 1999, 1: 43 - 56
Quiroga J.Cisneros C.Insuasty B.Abonía R.Nogueras M.Sánchez A. Tetrahedron Lett. 2001, 42: 5625 - 57
Lee HK.Chui WK. Bioorg. Med. Chem. 1999, 7: 1255 - 58
Modest EJ. J. Org. Chem. 1956, 21: 1 - 59
Suginome M.Ohmori Y.Ito Y. Chem. Commun. 2001, 1090 - 60
Billet M.Klotz PH.Mann A. Tetrahedron Lett. 2001, 42: 631 - 61 For example see:
Ishihara K.Funahashi M.Hanaki N.Miyata M.Yamamoto H. Synlett 1994, 963 - 62
Kobayashi S. Synlett 1994, 689 - 63
Kobayashi S.Hachiya I. J. Org. Chem. 1994, 59: 3590 - 64
Kobayashi S.Hachiya I.Takahori T.Araki M.Ishitani H. Tetrahedron Lett. 1992, 33: 6815 - 65
Hachiya I.Kobayashi S. J. Org. Chem. 1993, 58: 6958 - 66
Narasaka K.Tanaka H.Kanai F. Bull. Chem. Soc. Jpn. 1991, 64: 387 - 67
Kawada A.Mitamura S.Kobayashi S. Chem. Commun. 1993, 1157 - 68
Hachiya I.Kobayashi S. Tetrahedron Lett. 1994, 35: 3319 - 69
Kobayashi S.Hachiya I.Ishitana H.Araki M. Tetrahedron Lett. 1993, 34: 4535 - 70
Kobayashi S.Ishitani H.Nagayama S. Synthesis 1995, 1195 - 71 For example see:
Martens J.Scheunemann M. Tetrahedron Lett. 1991, 32: 1417 - 72 For example see:
Aggarwal VK.Thompson A.Jones RVH.Standen MCH. J. Org. Chem. 1996, 61: 8368 - 73
Nagayama S.Kobayashi S. Chem. Lett. 1998, 6852 - 74
Kubo T.Sakaguchi S.Ishii Y. Chem.Commun. 2000, 625 - 75
Annunziata R.Cinquini M.Cozzi F.Molteni V.Schupp O. J. Org. Chem. 1996, 61: 8293 - 76
Okitsu O.Oyamada H.Furuta T.Kobayashi S. Heterocycles 2000, 52: 1143 - 77
Palomo C.Aizpurua JM.Gracenea JJ.García-Granda S.Pertierra P. Eur. J. Org. Chem. 1998, 2201 - 78
Annunziata R.Cinquini M.Cozzi F.Molteni V.Schupp O. Tetrahedron 1996, 52: 2573 -
79a
Hirai K.Iwano Y.Mikoshiba I.Koyama H.Nishi T. Heterocycles 1994, 38: 277 -
79b
Hirai K.Homma H.Mikoshiba I. Heterocycles 1994, 38: 281 - 80
Oyamada H.Kobayashi S. Synlett 1998, 249 - 81
Kobayashi S.Hamada T.Manabe K. Synlett 2001, 1140 - 82
Kobayashi S.Akiyama R.Moriwaki M. Tetrahedron Lett. 1997, 38: 4819 - 83
Blackburn CH.Guan B.Fleming P.Shiosaki K.Tsai S. Tetrahedron Lett. 1998, 39: 3635 - 84
Kobayashi S.Akiyama R.Moriwaki M. Tetrahedron Lett. 1997, 38: 4819 - 85
Kobayashi S.Tamura M.Mukaiyama T. Chem. Lett. 1988, 91 - 86
Shiraishi H.Kawasaki Y.Sakaguchi S.Nishiyama Y.Ishii Y. Tetrahedron Lett. 1996, 37: 7291 - 87
Shiraishi H.Nishitani T.Sakaguchi S.Ishii Y. J. Org. Chem. 1998, 63: 6234 - 88
Nishitani T.Shiraishi H.Sakaguchi S.Ishii Y. Tetrahedron Lett. 2000, 41: 3389 -
89a
McKillop A.Young DW. Synthesis 1979, 401 -
89b
McKillop A.Young DW. Synthesis 1979, 481 - 90
Varma RS.Kumar D. Tetrahedron Lett. 1999, 40: 7665 -
91a
Balalaie S.Arabanian A. Green Chem. 2000, 2: 274 -
91b
Usyatinsky AY.Khmelnitsky YL. Tetrahedron Lett. 2000, 41: 5031 - 92
Ranu BC.Hajra A.Jana U. Synlett 2000, 75 - 93
Stoeck V.Schunack W. Arch. Pharmaz. 1974, 307: 922 -
94a
Stoeck V.Schunack W. Arch. Pharm. 1976, 309: 421 -
94b
Lipshutz BH.Morey MC. J. Org. Chem. 1983, 48: 3745 -
94c
Peddibhotla S.Jayakumar S.Tepe JJ. Org. Lett. 2002, 4: 3533 -
95a
Schubert H.Stodolka H. J. Prakt. Chem. 1963, 22: 130 -
95b
Krieg B.Manecke G. Z. Naturforsch., B: Chem. Sci. 1967, 22: 132 -
95c
Dghaym RD.Dhawan R.Arndtsen BA. Angew. Chem. Int. Ed. 2002, 40: 3228 -
96a
Varma RS.Dahiya R. J. Org. Chem. 1998, 63: 8038 -
96b
Varma RS. Tetrahedron 2002, 58: 1235 - 97
Sonogashira K. Metal-catalyzed Cross-coupling ReactionsDiederich F.Stang PJ. Wiley-VCH; Weinheim: 1998. p.203 - 98
Müller TJJ.Ansorge M.Aktah D. Angew. Chem. Int. Ed. 2000, 39: 1323; Angew. Chem. 2000, 112, 1323 - 99
Müller TJJ.Braun R.Ansorge M. Org. Lett. 2000, 2: 1967 - 100
Braun RU.Zeitler K.Müller TJJ. Org. Lett. 2000, 2: 4181 - 101
Chaplin JH.Flynn BL. Chem. Commun. 2001, 1594 - 102
Flynn BL.Verdier-Pinard P.Hamel E. Org. Lett. 2001, 3: 651 - 103
Braun RU.Zeitler K.Müller TJJ. Org. Lett. 2001, 3: 3297 - 104
Arcadi A.Cacchi S.Fabrizi G.Moro L. Eur. J. Org. Chem. 1999, 1137 - 105
Boykin DW.Kumar A.Bajic M.Xiao G.Wilson WD.Bender BC.McCurdy DR.Hall JE.Tidwell RR. Eur. J. Med. Chem. 1997, 32: 965 - 106
Balme G.Bouyssi D.Faure R.Gore J.Van Hemelryck B. Tetrahedron 1992, 48: 3891 - 107
Cavicchioli M.Sixdenier E.Derrey A.Bouyssi D.Balme G. Tetrahedron Lett. 1997, 38: 1763 -
108a
Bottex M.Cavicchioli M.Hartmann B.Monteiro N.Balme G. J. Org. Chem. 2001, 66: 175 -
108b
Azoulay S.Monteiro N.Balme G. Tetrahedron Lett. 2002, 43: 9311 -
108c
Clique B.Vassiliou S.Monteiro N.Balme G. Eur. J. Org. Chem. 2002, 1493 - 109
Clique B.Monteiro N.Balme G. Tetrahedron Lett. 1999, 40: 1301 - 110
Hayes JF.Shipman M.Twin H. Chem. Commun. 2000, 1791 -
111a
Hayes JF.Shipman M.Twin H. Chem. Commun. 2001, 1784 -
111b
Hayes JF.Shipman M.Twin H. J. Org. Chem. 2002, 67: 935 - 112
Kobayashi S.Ishitani H.Nagayama S. Chem. Lett. 1995, 423 - 113
Ali T.Chauhan KK.Frost ChG. Tetrahedron Lett. 1999, 40: 5621 -
114a
Akiyama T.Takaya J.Kagoshima H. Tetrahedron Lett. 1999, 40: 7831 -
114b
Akiyama T.Matsuda K.Fuchibe K. Synlett 2002, 1898 -
114c
Yuan Y.Li X.Ding K. Org. Lett. 2002, 4: 3309 -
115a
Annunziata R.Cinquini M.Cozzi F.Molteni V.Schupp O. Tetrahedron 1997, 53: 9715 -
115b
Annunziata R.Benaglia M.Ciquini M.Cozzi F. Eur. J. Org. Chem. 2002, 1184 -
116a
Schmidt RR. Angew. Chem., Int. Ed. Engl. 1973, 12: 212 -
116b
Shono T.Matsumura Y.Inoue K.Ohmizu H.Kashimura S. J. Am. Chem. Soc. 1982, 104: 5753 - 117
Kobayashi S.Nagayama S. J. Am. Chem. Soc. 1996, 118: 8977 - 118
Baudelle R.Melnyk P.Déprez B.Tartar A. Tetrahedron 1998, 54: 4125 - 119
Sartori G.Bigi F.Maggi R.Mazzacani A.Oppici G. Eur. J. Org. Chem. 2001, 2513 - 120
Batey RA.Simoncic PD.Lin D.Smyj RP.Lough AJ. Chem. Commun. 1999, 651 -
121a
Batey RA.Powell DA. Chem. Commun. 2001, 2362 -
121b
Powell DA.Batey RA. Org. Lett. 2002, 4: 2913 - 122
Wamhoff H.Schmidt A. J. Org. Chem. 1993, 58: 6976 - 123
Wamhoff H.Bamberg CH.Herrmann S.Nieger M. J. Org. Chem. 1994, 59: 3985 - 124
Cravotto G.Nano GM.Palmisano G.Pilati T.Tagliapietra S. J. Heterocycl. Chem. 2001, 38: 965 - 125
Appendino G.Cravotto G.Minassi A.Palmisano G. Eur. J. Org. Chem. 2001, 3711 - 126
Nair V.Vinod AU. Chem. Commun. 2000, 1019 - 127
Nair V.Vinod AU.Nair JS.Sreekanth AR.Rath NP. Tetrahedron Lett. 2000, 41: 6675 -
128a
Nair V.Vinod AU.Rajesh C. J. Org. Chem. 2001, 66: 4427 -
128b
Nair V.Sreekanth AR.Abhilash N.Bhadbhade MM.Gonnade RC. Org. Lett. 2002, 4: 3575 - 129
Kobayashi S.Akiyama R.Kawamura M.Ishitani H. Chem. Lett. 1997, 1039 - 130
McKiernan MT.Heaney F. Tetrahedron Lett. 1996, 37: 4597 - 131
Righi P.Marotta E.Rosini G. Chem.-Eur. J. 1998, 4: 2501 - 132
Avalos M.Babiano R.Cintas P.Jiménez JL.Palacios JC.Silva MA. Chem.Commun. 1998, 459 - 133
Avalos M.Babiano R.Cintas P.Higes FJ.Jiménez JL.Palacios JC.Silva MA. J. Org. Chem. 1999, 64: 1494 - 134
Fokas D.Ryan WJ.Casebier DS.Coffen DL. Tetrahedron Lett. 1998, 39: 2235 - 135
Nair V.Sheela KC.Rath NP.Eigendorf GK. Tetrahedron Lett. 2000, 41: 6217 -
136a
Ardil H.Grigg R.Shridharan V.Surendrakumar S.Thianpatanagul S.Kanajun S. Chem. Commun. 1986, 602 -
136b
Blaney P.Grigg R.Rankovic Z.Thornton-Pett M.Xu J. Tetrahedron 2002, 58: 1719 -
136c
Grigg R.Koppen I.Rasparini M.Sridharan V. Chem. Commun. 2001, 964 -
136d
Casaschi A.Grigg R.Sansano JM. Tetrahedron 2001, 57: 607