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Synthesis 2007(5): 675-678
DOI: 10.1055/s-2007-965922
DOI: 10.1055/s-2007-965922
PAPER
© Georg Thieme Verlag Stuttgart · New York
A Rapid and Efficient Synthesis of Benzimidazoles Using Hypervalent Iodine as Oxidant
Further Information
Received
16 October 2006
Publication Date:
08 February 2007 (online)
Publication History
Publication Date:
08 February 2007 (online)
Abstract
Various 2-arylbenzimidazoles were synthesized from phenylenediamines and aldehydes via a one-step process using hypervalent iodine as an oxidant. The salient features of this method include mild conditions, short reaction times (3-5 min), high yields, and simple procedure.
Key words
benzimidazoles - iodobenzene diacetate (IBD) - oxidations - o-phenylenediamines
-
1a
Erhardt PW. J. Med. Chem. 1987, 30: 231 -
1b
Tomczuk BE.Taylor CR.Moses LM.Sutherland DB.Lo YS.Johnson DN.Kinnier WB.Kilpatrick BF. J. Med. Chem. 1991, 34: 2993 -
1c
Spasov AA.Yozhitsa IN.Bugaeva LI.Anisimova VA. Pharm. Chem. J. 1999, 33: 232 -
1d
Preston PN. Chem. Heterocycl. Compd. 1980, 40: 531 -
1e
Zimmer C.Wahnert U. Prog. Biophys. Mol. Biol. 1986, 47: 31 -
1f
Gravatt GL.Baguley BC.Wilson WR.Denny WA. J. Med. Chem. 1994, 37: 4338 -
1g
Soderlind K.-J.Gorodetsky B.Singh AK.Bachur N.Miller GG.Lown JW. Anti-Cancer Drug Des. 1999, 14: 19 -
2a
Kim JS.Gatto B.Yu C.Liu A.Liu LF.LaVoie EJ. J. Med. Chem. 1996, 39: 992 -
2b
Chen AY.Yu C.Gatto B.Liu LF. Proc. Natl. Acad. Sci. U.S.A. 1993, 90: 8131 -
2c
Woynarowski JM.McHugh MM.Sigmud RD.Beerman TA. Mol. Pharmacol. 1989, 35: 177 - 3
Roth T.Morningstar ML.Boyer PL.Hughes SH.Buckheit RW.Michejda CJ. J. Med. Chem. 1997, 40: 4199 -
4a
Grimmet MR. In Comprehensive Heterocyclic Chemistry Vol. 5:Katritzky AR.Rees CW. Pergamon Press; Oxford: 1984. p.457 -
4b
Wright JB. Chem. Rev. 1951, 48: 397 -
4c
Middleton RW.Wibberley DG. J. Heterocycl. Chem. 1980, 17: 1757 -
4d
Hisano T.Ichikawa M.Tsumoto K.Tasaki M. Chem. Pharm. Bull. 1982, 30: 2996 -
4e
Geratz JD.Stevens FM.Polakoski KL.Parrish RF. Arch. Biochem. Biophys. 1979, 197: 551 -
5a
Czarny A.Wilson WD.Boykin DW. J. Heterocycl. Chem. 1996, 33: 1393 -
5b
Tidwell RR.Geratz JD.Dann O.Volz G.Zeh D.Loewe H. J. Med. Chem. 1978, 21: 613 -
5c
Fairley TA.Tidwell RR.Donkor I.Naiman NA.Ohemeng KA.Lombardy RJ.Bentley JA.Cory M. J. Med. Chem. 1993, 36: 1746 -
6a
Bourgrin K.Loupy A.Soufiaoui M. Tetrahedron 1998, 54: 8055 -
6b
Reddy GV.Rao VVVNSR.Narsaiah B.Rao PS. Synth. Commun. 2002, 32: 2467 -
6c
Ben-Alloum A.Bakkas S.Soufiaoui M. Tetrahedron Lett. 1998, 39: 4481 -
7a
Dubey PK.Ratnam CV. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1979, 18: 428 -
7b
Yadagiri B.Lown JW. Synth. Commun. 1990, 20: 955 -
7c
Bathini Y.Rao KE.Shea RG.Lown JW. Chem. Res. Toxicol. 1990, 3: 268 -
7d
Singh MP.Joseph T.Kumar S.Bathini Y.Lown JW. Chem. Res. Toxicol. 1992, 5: 597 -
7e
Harapanhalli RS.McLaughlin LW.Howell RW.Rao DV.Adelstein SJ.Kassis AI. J. Med. Chem. 1996, 39: 4804 -
8a
Verner E.Katz BA.Spencer JR.Allen D.Hataye J.Hruzewicz W.Hui HC.Kolesnikov A.Li Y.Luong C.Martelli A.Radika K.Rai R.She M.Shrader W.Sprengeler PA.Trapp S.Wang J.Young WB.Mackman RL. J. Med. Chem. 2001, 44: 2753 -
8b
Kumar S.Kansal V.Bhaduri A. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1991, 20: 254 -
9a
vanden Eynde JJ.Delfosse F.Lor P.van Haverbeke Y. Tetrahedron 1995, 51: 5813 -
9b
Lee KJ.Janda KD. Can. J. Chem. 2001, 79: 1556 - 10
Chikashita H.Nishida S.Miyazaki M.Morita Y.Itoh K. Bull. Chem. Soc. Jpn. 1987, 60: 737 - 11
Patzold F.Zeuner F.Heyer TH.Niclas HJ. Synth. Commun. 1992, 22: 281 - 12
Bhatnagar I.George MV. Tetrahedron 1968, 24: 1293 - 13
Stephens FF.Bower JD. J. Chem. Soc. 1949, 2971 - 14
Beaulieu PL.Haché B.von Moos E. Synthesis 2003, 1683 -
15a
Weidner-Wells MA.Ohemeng KA.Nguyen VN.Fraga-Spano S.Macielag MJ.Werblood HM.Foleno BD.Webb GC.Barrett JF.Hlasta DJ. Bioorg. Med. Chem. Lett. 2001, 11: 1545 -
15b
Austen SC.Kane JM. J. Heterocycl. Chem. 2001, 38: 979 - 16
Lombardy RL.Tanious FA.Ramachandran K.Tidwell RR.Wilson WD. J. Med. Chem. 1996, 39: 1452 - 17
Lin S.Yang L. Tetrahedron Lett. 2005, 46: 4315 - 18
Gogoi P.Konwar D. Tetrahedron Lett. 2006, 47: 79 -
19a
Stang PJ.Zhdankin VV. Chem. Rev. 1996, 1123 -
19b
Togo H.Harda Y.Yokoyama M. J. Org. Chem. 2000, 65: 926 -
19c
Ohno M.Oguri I.Eguchi S. J. Org. Chem. 1999, 64: 8995 -
19d
Adam W.Hajra S.Herderich M.Saha-Moeller CR. Org. Lett. 2000, 2: 2773 -
19e
Braun NA.Ousmer M.Bray JD.Bouchu D.Peters K.Peters E.-M.Ciufolini MA. J. Org. Chem. 2000, 65: 4397 -
19f
Chen DW.Chen ZC. Tetrahedron Lett. 1994, 35: 7637 -
19g
Varma RS.Saini RK.Prakash O. Tetrahedron Lett. 1997, 38: 2621 - 20
Ramsden CA.Rose HL. J. Chem. Soc., Perkin Trans. 1 1997, 2319 - 21
Jung MH.Park JM.Lee IYC.Ahn M. J. Heterocycl. Chem. 2003, 40: 37 - 22
Abdelkrim BA. Tetrahedron Lett. 2003, 44: 5935 - 23
Speier G. J. Org. Chem. 1986, 51: 218 - 24
Bougrin K.Loupy A.Soufiaoui M. Tetrahedron 1998, 54: 8055 - 25
Cohen VI. J. Heterocycl. Chem. 1979, 16: 13 - 26
Perry RJ.Wilson BD. J. Org. Chem. 1993, 58: 7016 - 27
George B.Papadopoulos EP. J. Org. Chem. 1977, 42: 441