Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2012(6): 927-933
DOI: 10.1055/s-0031-1289692
DOI: 10.1055/s-0031-1289692
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Iodine-Mediated Intramolecular Oxidative Cyclization of 2-(Styrylthio)anilines: Synthesis of 2-Substituted Benzothiazoles
Further Information
Received
23 November 2011
Publication Date:
06 February 2012 (online)
Publication History
Publication Date:
06 February 2012 (online)
Abstract
A novel metal-free iodine-mediated intramolecular oxidative cyclization protocol is presented, which allows for the preparation of various 2-substituted benzothiazoles.
Key words
iodine - oxidation - cyclization - 2-(styrylthio)aniline - benzothiazole
- Supporting Information for this article is available online:
- Supporting Information
- For selected recent papers, see:
-
1a
Wang M.Gao MZ.Mock BH.Miller KD.Sledge GW.Hutchins GD.Zheng QH. Bioorg. Med. Chem. 2006, 14: 8599 -
1b
Lion CJ.Matthews CS.Wells G.Bradshaw TD.Stevens MFG.Westwell AD. Bioorg. Med. Chem. Lett. 2006, 16: 5005 -
1c
Mortimer CG.Wells G.Crochard JP.Stone EL.Bradshaw TD.Stevens MFG.Westwell AD. J. Med. Chem. 2006, 49: 179 -
1d
Kamal A.Khan M.Naseer A.Reddy KS.Srikanth YVV.Sridhar B. Chem. Biol. Drug Des. 2008, 71: 78 -
1e
Kok SHL.Gambari R.Chui CH.Yuen MCW.Lin E.Wong RSM.Lau FY.Cheng GYM.Lam WS.Chan SH.Lam KH.Cheng CH.Lai PBS.Yu MWY.Cheung F.Tang JCO.Chan ASC. Bioorg. Med. Chem. 2008, 16: 3626 -
1f
Liu C.Lin J.Pitt S.Zhang RF.Sack JS.Kiefer SE.Kish K.Doweyko AM.Zhang H.Marathe PH.Trzaskos J.Mckinnon M.Dodd JH.Barrish JC.Schieven GL.Leftheris K. Bioorg. Med. Chem. Lett. 2008, 18: 1874 -
1g
Henriksen G.Hauser AI.Westwell AD.Yousefi BH.Schwaiger M.Drzezga A.Wester HJ. J. Med. Chem. 2007, 50: 1087 - For cyclocondensation-dehydration process, see:
-
2a
Mu XJ.Zou JP.Zeng RS.Wu JC. Tetrahedron Lett. 2005, 46: 4345 -
2b
Bose DS.Idrees M. J. Org. Chem. 2006, 71: 8261 -
2c
Hioki H.Matsushita K.Kubo M.Harada K.Kodama M.Fukuyama Y. Tetrahedron 2007, 63: 11315 -
2d
Boger DE. J. Org. Chem. 1978, 43: 2296 -
2e
Terashima M.Ishii M.Kanaoka Y. Synthesis 1982, 484 -
2f
Ben-Alloum A.Bakkas S.Soufiaoui M. Tetrahedron Lett. 1997, 38: 6395 -
2g
Ben-Alloum A.Bakkas S.Soufiaoui M. Tetrahedron Lett. 1997, 38: 6395 -
2h
Ryabukhin SV.Plaskon AS.Volochnyuk DM.Tolmachev AA. Synthesis 2006, 3715 -
2i
Kawashita Y.Ueba C.Hayashi M. Tetrahedron Lett. 2006, 47: 4231 -
2j
Li Y.Wang YL.Wang JY. Chem. Lett. 2006, 35: 460 -
2k
Bahrami K.Khodaei MM.Naali F. J. Org. Chem. 2008, 73: 6835 -
2l
Chen YX.Qian LF.Zhang W.Han B. Angew. Chem. Int. Ed. 2008, 47: 9330 -
2m
Metzger JV. In Comprehensive Heterocyclic Chemistry Vol. 6:Katritzsky AR.Rees CW. Pergamon Press; Oxford: 1984. p.322 - For N-(2-haloaryl)thioamides as substrates, with Pd:
-
3a
Couture A.Granclaudon P. Heterocycles 1984, 22: 1383 -
3b
Benedí C.Bravo F.Uriz P.Fernández E.Claver C.Castillón S. Tetrahedron Lett. 2003, 44: 6073 -
3c
Itoh T.Mase T. Org. Lett. 2007, 9: 3687 -
3d
Vera MD.Pelletier JC. J. Comb. Chem. 2007, 9: 569 - With Pd or Cu:
-
3e
Joyce LL.Evindar G.Batey RA. Chem. Commun. 2004, 446 - With Cu:
-
3f
Evindar G.Batey RA. J. Org. Chem. 2006, 71: 1802 - For N-Arylthioamides as the substrates, with Pd/Cu:
-
4a
Inamoto K.Hasegawa C.Hiroya K.Doi T. Org. Lett. 2008, 10: 5147 - With Cu:
-
4b
Ueda S.Nagasawa H. Angew. Chem. Int. Ed. 2008, 47: 6411 -
5a
Ding Q.He X.Wu J. J. Comb. Chem. 2009, 11: 587 -
5b
Pi SS.Zhang XG.Tang RY.Li JH. Synlett 2009, 3032 -
5c
Qiu J.-W.Zhang XG.Tang RY.Zhong P.Li JH. Adv. Synth. Catal. 2009, 351: 2319 -
5d
Shen G.-D.Lv X.Bao W.-L. Eur. J. Org. Chem. 2009, 5897 -
5e
Ding Q.-P.Cao B.-P.Liu X.-J.Zong Z.-Z.Peng Y.-Y. Green Chem. 2010, 12: 1607 -
5f
Guo YJ.Tang RY.Zhong P.Li JH. Tetrahedron Lett. 2010, 51: 649 -
6a
Saha D.Adak L.Ranu BC. Tetrahedron Lett. 2010, 51: 5624 -
6b
Xie K.Yang ZY.Zhou XJ.Li XJ.Wang SZ.Tan Z.An XY.Guo CC. Org. Lett. 2010, 12: 1564 -
6c
Huang JK.Chan J.Chen Y.Borths CJ.Baucom KD.Larsen RD.Faul MM. J. Am. Chem. Soc. 2010, 132: 3674 -
6d
Hachiya H.Hirano K.Satoh T.Miura M. Org. Lett. 2009, 11: 1737 -
6e
Canivet J.Yamaguchi J.Ban I.Itami K. Org. Lett. 2009, 11: 1733 -
6f
Derridj F.Roger J.Geneste F.Djebbar S.Doucet H. J. Organomet. Chem. 2009, 694: 455 -
6g
Alagille D.Baldwin RM.Tamagnan GD. Tetrahedron Lett. 2005, 46: 1349 -
7a
Banerjee AK.Laya MS.Cabrera EV. Curr. Org. Chem. 2011, 15: 1058 -
7b
Mphahlele MJ. Molecules 2009, 14: 4814 -
7c
Togo H.Iida S. Synlett 2006, 2159 -
7d
Martins da Silva F.Jones J.de Mattos MCS. Curr. Org. Synth. 2005, 2: 393 -
7e
Larock RC. In Acetylene ChemistryDiederich F.Stang PJ.Tykwinski RR. Wiley-VCH; Weinheim: 2005. p.P51-P99 - For selected recent papers on N-heterocyclization via iodocyclizations of alkynes, see:
-
8a
Zora M.Kivrak A.Yazici C. J. Org. Chem. 2011, 76: 6726 -
8b
Ali S.Zhu H.-T.Xia X.-F.Ji K.-G.Yang Y.-F.Song X.-R.Liang Y.-M. Org. Lett. 2011, 13: 2598 -
8c
Okitsu T.Sato K.Potewar TM.Wada A. J. Org. Chem. 2011, 76: 3438 -
8d
Ouyang H.-C.Tang R.-Y.Zhong P.Zhang X.-G.Li J.-H. J. Org. Chem. 2011, 76: 223 -
8e
Okitsu T.Sato K.Wada A. Org. Lett. 2010, 12: 3506 -
8f
Mehta S.Larock RC. J. Org. Chem. 2010, 75: 1652 -
8g
Worlikar SA.Neuenswander B.Lushington GH.Larock RC. J. Comb. Chem. 2009, 11: 875 -
8h
Cherry K.Duchene A.Thibonnet J.Parrain J.-L.Anselmi E.Abarbri M. Synthesis 2009, 257 -
8i
Choi J.Lee GH.Kim I. Synlett 2008, 1243 -
8j
Knight DW.Rost HC.Sharland CM.Singkhonrat J. Tetrahedron Lett. 2007, 48: 7906 -
8k
Hessian KO.Flynn BL. Org. Lett. 2006, 8: 243 -
8l
Yao T.Yue D.Larock RC. J. Org. Chem. 2005, 70: 9985 -
8m
Yue D.Larock RC. Org. Lett. 2004, 6: 1037 - For selected recent papers on O-heterocyclization via iodocyclizations of alkynes, see:
-
9a
Cho C.-H.Larock RC. ACS Comb. Sci. 2011, 13: 272 -
9b
Raffa G.Belot S.Balme G.Monteiro N. Org. Biomol. Chem. 2011, 9: 1474 -
9c
Chen Z.-W.Huang G.Jiang H.-F.Huang H.-W.Pan X.-Y. J. Org. Chem. 2011, 76: 1134 -
9d
Verma AK.Rustagi V.Aggarwal T.Singh AP. J. Org. Chem. 2010, 75: 7691 -
9e
Mancuso R.Mehta S.Gabriele B.Salerno G.Jenks WS.Larock RC. J. Org. Chem. 2010, 75: 897 -
9f
Roy S.Roy S.Neuenswander B.Hill D.Larock RC. J. Comb. Chem. 2009, 11: 1128 -
9g
Okitsu T.Nakazawa D.Taniguchi R.Wada A. Org. Lett. 2008, 10: 4967 -
9h
Waldo JP.Mehta S.Neuenswander B.Lushington GH.Larock RC. J. Comb. Chem. 2008, 10: 658 -
9i
Arimitsu S.Jacobsen JM.Hammond GB.
J. Org. Chem. 2008, 73: 2886 -
9j
Aillaud I.Bossharth E.Conreaux D.Desbordes P.Monteiro N.Balme G. Org. Lett. 2006, 8: 1113 - For selected recent papers on the iodocyclizations of alkenes, see:
-
10a
Mohapatra DK.Bhimireddy E.Krishnarao PS.Das PP.Yadav JS. Org. Lett. 2011, 13: 744 -
10b
Miyagawa T.Nagai K.Yamada A.Sugihara Y.Fukuda T.Fukuda T.Uchida R.Tomoda H.Omura S.Nagamitsu T. Org. Lett. 2011, 13: 1158 -
10c
Davies D.Fletcher MD.Franken H.Hollinshead J.Kaehm K.Murphy PJ.Nash R.Potter DM. Tetrahedron Lett. 2010, 51: 6825 -
10d
Pradal A.Nasr A.Toullec PY.Michelet V. Org. Lett. 2010, 12: 5222 -
10e
Chen J.Lu L.Ma SM. Tetrahedron 2008, 64: 8899 -
10f
Sakakura A.Ukai A.Ishihara K. Nature 2007, 445: 900 -
10g
Amjad M.Knight DW. Tetrahedron Lett. 2006, 47: 2825 -
11a
Downer-Riley NK.Jackson YA. Tetrahedron 2007, 63: 10276 -
11b
Il’inykh ES.Kim DG. Chem. Heterocycl. Compd. 2011, 47: 636 -
11c
Creeke PI.Mellor JM. Tetrahedron Lett. 1989, 30: 4435 - 12
Wang ZL.Tang RY.Luo PS.Deng CL.Zhong P.Li JH. Tetrahedron 2008, 64: 10670 - Further investigation demonstrated that by loading bases like NaHCO3 and K2CO3 (2 equiv), or lowering the amount of iodine (0.5 equiv), the reactivity of substrate 1i did not increase and only trace product was observed. For relative references, see:
-
13a
Huang Q.-H.Hunter JA.Larock RC. Org. Lett. 2001, 3: 2973 -
13b
Zhang XX.Campo MA.Yao T.-L.Larock RC. Org. Lett. 2005, 7: 763 - 14
Takashi N.Hideki Y.Koichiro O. Org. Lett. 2007, 9: 2373 - 15
Tekiner-Gulbas B.Filak L.Vasko GA.Egyed O.Yalcin I. Heterocycles 2008, 75: 2005 - 16
Nutaitis CF.Swartz BD. Org. Prep. Proced. Int. 2005, 37: 507 - 17
Hamer FM. J. Chem. Soc. 1956, 1480 - 18
Kendall JD, andDuffin GF. inventors; Patent GB 829832. ; Chem. Abstr. 1960, 54, 91775 - 19
Cossey HD.Judd J.Stephens FF. J. Chem. Soc. 1965, 954