RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000083.xml
Synlett 2007(20): 3096-3102
DOI: 10.1055/s-2007-992384
DOI: 10.1055/s-2007-992384
ACCOUNT
© Georg Thieme Verlag Stuttgart · New York
Position-Flexible Elaboration of Halogenated Heterocycles: Metalated Species as Key Intermediates for Synthesis
Weitere Informationen
Received
18 September 2007
Publikationsdatum:
03. Dezember 2007 (online)
Publikationsverlauf
Publikationsdatum:
03. Dezember 2007 (online)
Abstract
Halogens, in particular fluorine atoms, are favorite tools to fine-tune the chemical and biological properties of pharmaceutical or agricultural development products. At the same time, such an electronegative substituent can effectively assist the site-selective functionalization of an aromatic or heterocyclic core compound by directing a metal to the targeted position, the metal acting as a harbinger for the definitive substituent. The concept is illustrated by typical examples selected from the carbazole, indole, pyrrole, pyrazole, imidazole, pyridine, quinoline and pyrimidine fields.
1 Introduction
2 Carbazoles and Indoles
3 Pyrroles, Pyrazoles and Imidazoles
4 Pyridines, Quinolines and Pyrimidines
5 Conclusions and Outlook
Key Words
fluorine - functionalization - halogens - organometallic reagents - organic synthesis - regioselectivity
- 1
Comprehensive Medicinal Chemistry
Vol. 1-6:
Hansch C.Sammes PG.Taylor JB.Colin J.Emmett JC.Kennewell PD.Ramsden CA. Pergamon Press; Oxford: 1990. - 2
Garner P.Kaniskan HU.Hu JY.Youngs WJ.Panzner M. Org. Lett. 2006, 8: 3647 - 3
Bleicher KH.Nettekoven M.Peters JU.Wyler R. Chimia 2004, 58: 588 - 4
Lipinski CA.Lombardo F.Dominy BW.Feeney PJ. Adv. Drug Del. Rev. 1997, 23: 3 ; Chem. Abstr. 1997, 126, 162025 - 5
Schlosser M. In Organometallics in Synthesis: A Manual Vol. 2:Schlosser M. Wiley; Chichester: 2002. p.1-352 - 6
Gilman H.Kirby RH. J. Org. Chem. 1936, 1: 146 - 7
Gilman H.Gray S. J. Org. Chem. 1958, 23: 1476 - 8
Katritzky AR.Rewcastle GW.Demiguel LMV. J. Org. Chem. 1988, 53: 794 - 9
Shirley DA.Roussel PA. J. Am. Chem. Soc. 1953, 75: 375 - 10
Ziegler FE.Spitzner EB. J. Am. Chem. Soc. 1970, 92: 3492 - 11
Sundberg RJ.Russell HF. J. Org. Chem. 1973, 38: 3324 - 12
Hasan I.Marinelli ER.Lin LCC.Fowler FW.Levy AB. J. Org. Chem. 1981, 46: 157 - 13
Hlasta DJ.Bell MR. Heterocycles 1989, 29: 849 - 14
Katritzky AR.Lue P.Chen YX. J. Org. Chem. 1990, 55: 3688 - 15
Sundberg RJ.Parton RL. J. Org. Chem. 1976, 41: 163 - 16
Schlosser M. Angew. Chem. Int. Ed. 2005, 44: 376 ; Angew. Chem. 2005, 117, 380 - 17
Schlosser M.Ginanneschi A.Leroux F. Eur. J. Org. Chem. 2006, 2956 - 19
Shirley DA.Gross BH.Roussel PA. J. Org. Chem. 1955, 20: 225 - 20
Gjøs N.Gronowitz S. Acta Chem. Scand. 1971, 25: 2596 - 21
Wrackmeyer B.Nöth H. Chem. Ber. 1976, 109: 1075 - 22
Muchowski JM.Solas DR. J. Org. Chem. 1984, 49: 203 - 23
Faigl F.Schlosser M. Tetrahedron 1993, 49: 10271 - 24
Chen W.Stephenson EK.Cava MP.Jackson YA. Org. Synth. 1992, 70: 151 - 25
Muchowski JM.Naef R. Helv. Chim. Acta 1984, 67: 1168 - 26
Kozikowski AP.Cheng XM. J. Org. Chem. 1984, 49: 3239 - 27
Nguyên DL.Schlosser M. Helv. Chim. Acta 1977, 60: 2085 - 28
Schick JW.Hartough HD. J. Am. Chem. Soc. 1948, 70: 286 - 29
Schlosser M.Volle J.-N.Leroux F.Schenk K. Eur. J. Org. Chem. 2002, 2913 - 30
Shirley DA.Alley PW. J. Am. Chem. Soc. 1957, 79: 4922 - 31
Roe AM. J. Chem. Soc. 1963, 2195 - 32
Whitten JP.Matthews DP.Mccarthy JR. J. Org. Chem. 1986, 51: 1891 - 33
Tertov BA.Burykin VV.Sadekov ID. Khim. Geterotsikl. Soedin. 1969, 560 ; Chem. Abstr. 1969, 71, 124328 - 34
Noyce DS.Stowe GT.Wong W. J. Org. Chem. 1974, 39: 2301 - 35
Iddon B. Heterocycles 1985, 23: 417 - 36
Iddon B.Khan N. J. Chem. Soc., Perkin Trans. 1 1987, 1453 - 37
Iddon B.Khan N.Lim BL. J. Chem. Soc., Perkin Trans. 1 1987, 1457 - 38
Lipshutz BH.Hagen W. Tetrahedron Lett. 1992, 33: 5865 - 39
Groziak MP.Wei LL. J. Org. Chem. 1992, 57: 3776 - 40
Gribble GW.Saulnier MG. Tetrahedron Lett. 1980, 21: 4137 - 41
Gribble GW.Saulnier MG. Heterocycles 1993, 35: 151 - 42
Marsais F.Bréant P.Ginguène A.Quéguiner G. J. Organomet. Chem. 1981, 216: 139 - 43
Marsais F.Laperdrix B.Güngör T.Mallet M.Quéguiner G. J. Chem. Res., Synop. 1982, 278 - 44
Choppin S.Gros P.Fort Y. Org. Lett. 2000, 2: 803 - 45
Choppin S.Gros P.Fort Y. Eur. J. Org. Chem. 2001, 603 - 46
Bobbio C.Schlosser M. J. Org. Chem. 2005, 70: 3039 - 47
Marzi E.Bobbio C.Cottet F.Schlosser M. Eur. J. Org. Chem. 2005, 2116 - 48
Cottet F.Marull M.Lefebvre O.Schlosser M. Eur. J. Org. Chem. 2003, 1559 - 49
Schlosser M.Marull M. Eur. J. Org. Chem. 2003, 1569 - 50
Schlosser M.Mongin F. Chem. Soc. Rev. 2007, 36: 1161 - 51
Katsoulos G.Takagishi S.Schlosser M. Synlett 1991, 731 - 52
Mongin F.Maggi R.Schlosser M. Chimia 1996, 50: 650 - 53
Marzi E.Bigi A.Schlosser M. Eur. J. Org. Chem. 2001, 1371 - 54
Radinov R.Haimova M.Simova E. Synthesis 1986, 886 - 55
Radinov R.Chanev C.Haimova M. J. Org. Chem. 1991, 56: 4793 - 56
Gu YG.Bayburt EK. Tetrahedron Lett. 1996, 37: 2565 - 57
Cale AD.Gero TW.Walker KR.Lo YS.Welstead WJ.Jaques LW.Johnson AF.Leonard CA.Nolan JC.Johnson DN. J. Med. Chem. 1989, 32: 2178 - 58
Bobbio C.Rausis T.Schlosser M. Chem. Eur. J. 2005, 11: 1903 - 59
Schlosser M.Rausis T. Eur. J. Org. Chem. 2004, 1018 - 60
Coe PL.Stuart AM.Moody DJ. J. Fluorine Chem. 1998, 92: 27 - 61
Hatanaka Y.Hiyama T. Synlett 1991, 845 - 62
Cottet F.Schlosser M. Eur. J. Org. Chem. 2004, 3793 - 63
Cottet F.Marull M.Mongin F.Espinosa D.Schlosser M. Synthesis 2004, 1619 - 64
Schlosser M.Heiss C. Eur. J. Org. Chem. 2003, 4618 - 65
Marzi E.Gorecka J.Schlosser M. Synthesis 2004, 1609 - 66
Comins DL.Hong H.Saha JK.Gao JH. J. Org. Chem. 1994, 59: 5120 - 67
Quéguiner G.Marsais F.Snieckus V.Epsztajn J. Adv. Heterocycl. Chem. 1991, 52: 187 - 68
Marsais F.Bouley E.Quéguiner G. J. Organomet. Chem. 1979, 171: 273 - 69
Shi G.-q.Takagishi S.Schlosser M. Tetrahedron 1994, 50: 1129 - 70
Caubère P. Chem. Rev. 1993, 93: 2317 - 71
Gros P.Fort Y.Quéguiner G.Caubère P. Tetrahedron Lett. 1995, 36: 4791 - 72
Marull M.Schlosser M. Eur. J. Org. Chem. 2003, 1576 - 73
Lefebvre O.Marull M.Schlosser M. Eur. J. Org. Chem. 2003, 2115 - 74
Marull M.Lefebvre O.Schlosser M. Eur. J. Org. Chem. 2004, 54 - 75
Langley BW. J. Am. Chem. Soc. 1956, 78: 2136 - 76
Sandosham J.Undheim K. Tetrahedron 1994, 50: 275 - 77
Schlosser M.Lefebvre O.Ondi L. Eur. J. Org. Chem. 2006, 1593 - 78
Plé N.Turck A.Martin P.Barbey S.Quéguiner G. Tetrahedron Lett. 1993, 34: 1605 - 79
Plé N.Turck A.Heynderickx A.Quéguiner G. J. Heterocycl. Chem. 1994, 31: 1311 - 80
Plé N.Turck A.Heynderickx A.Quéguiner G. J. Heterocycl. Chem. 1997, 34: 551
References
Leroux, F.; Ginanneschi, A.; Schlosser, M. unpublished results, 2005.