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DOI: 10.1055/s-2007-965929
Synthesis of 2-Arylbenzothiazoles by DDQ-Promoted Cyclization of Thioformanilides; A Solution-Phase Strategy for Library Synthesis
Publikationsverlauf
Publikationsdatum:
08. Februar 2007 (online)
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Abstract
Several substituted benzothiazoles were synthesized by the intramolecular cyclization of thioformanilides using 2,6-dichloro-3,5-dicyano-1,4-benzoquinone (DDQ) in dichloromethane at ambient temperature in high yields. The resulting 2-arylbenzothiazoles were separated from the reduced DDQ byproduct 4,5-dichloro-3,6-dihydroxyphthalonitrile by treatment of the reaction mixture with a strongly basic ion-exchange resin. This protocol offers a high degree of flexibility with regard to the functional groups that can be placed on the benzothiazole ring or 2-aryl moiety, which in turn generates scaffolds for parallel synthesis.
Key words
thioformanilide - solution phase - cyclization - 2,6-dichloro-3,5-dicyano-1,4-benzoquinone - benzothiazole - sulfanyl radical
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1a
DeSimone RW.Currie KS.Mitchell SA.Darrow JW.Pippin DA. Comb. Chem. High Throughput Screening 2004, 7: 473 -
1b
Horton DA.Bourne GT.Smythe ML. Chem. Rev. 2003, 103: 893 -
2a
Mathis CA.Wang Y.Holt DP.Huang G.-F.Debnath ML.Klunk WE. J. Med. Chem. 2003, 46: 2740 -
2b
Hutchinson I.Jennings SA.Vishnuvajjala BR.Westwell AD.Stevens MFG. J. Med. Chem. 2002, 45: 744 -
2c
Alagille D.Baldwin RM.Tamagnan GD. Tetrahedron Lett. 2005, 46: 1349 - 3
Stevens MFG,Wells G,Westwell AD, andPoole TD. inventors; WO 03,004,479. ; Chem. Abstr., 2003, 138, 106698 - 4
Caujolle R.Loiseau P.Payard M.Gayral P.Kerhir MN. Ann. Pharm. Fr. 1989, 47: 68 - 5
Yamamoto K.Fujita M.Tabashi K.Kawashima Y.Kato E.Oya M.Iso T.Iwao J. J. Med. Chem. 1988, 31: 919 - 6
Yoshida H.Nakao R.Nohta H.Yamaguchi M. Dyes Pigm. 2000, 47: 239 - 7
Petkov I.Deligeorgiev T.Markov P.Evstatiev M.Fakirov S. Polym. Degrad. Stab. 1991, 33: 53 - 8
Ben-Alloum A.Bakkas S.Soufiaoui M. Tetrahedron Lett. 1997, 38: 6395 -
9a
Shi D.-F.Bradshaw TD.Wrigley S.McCall CJ.Lelieveld IF.Stevens MFG. J. Med. Chem. 1996, 39: 3375 -
9b
Klunk WE,Mathis CA, andWang Y. inventors; WO 2004,083,195. - 10
Hein DW.Alheim RJ.Leavitt JJ. J. Am. Chem. Soc. 1957, 79: 427 -
11a
Paul S.Gupta M.Gupta R. Synth. Commun. 2002, 32: 3541 -
11b
Kamila S.Koh B.Biehl ER. J. Heterocycl. Chem. 2006, 43: 1609 - 12
Shirinian VZ.Melkova SYu.Belen’kii LI.Krayushkin MM.Zelinsky ND. Russ. Chem. Bull. 2000, 49: 1859 - 13
Zhong WH.Zhang YM.Chen XY. J. Indian Chem. Soc. 2001, 78: 316 -
14a
Huang S.Connolly PJ. Tetrahedron Lett. 2004, 45: 9373 -
14b
Roe A.Tucker WP. J. Heterocycl. Chem. 1965, 2: 148 - 15
Stanetty P.Krumpark B. J. Org. Chem. 1996, 61: 5130 -
16a
Ares JJ. Synth. Commun. 1991, 21: 625 -
16b
Majo VJ.Prabhakaran J.Mann JJ.Kumar JSD. Tetrahedron Lett. 2003, 44: 8535 - 17
Tale RH. Org. Lett. 2002, 4: 1641 - 18
Nair V.Augustine A. Org. Lett. 2003, 5: 543 -
19a
Buckle DR. Encyclopedia of Reagents for Organic Synthesis Vol. 3:Paquette LA. John Wiley & Sons; Chichester: 1995. p.1699 -
19b
Bharate B. Synlett 2006, 496 -
19c
Zhang Y.Li C.-J. J. Am. Chem. Soc. 2006, 128: 4242 -
20a
Bose DS.Idrees Md. J. Org. Chem. 2006, 71: 8261 -
20b
Bose DS.Kumar RK. Tetrahedron Lett. 2006, 47: 813 -
20c
Bose DS.Fatima L.Rajender S. Synthesis 2006, 1863 -
20d
Bose DS.Idrees Md. J. Heterocycl. Chem. 2007, 44: 211 -
20e
Bose DS.Narsimha Reddy AV. Tetrahedron Lett. 2003, 44: 3543 -
21a
Thompson LA.Ellman JA. Chem. Rev. 1996, 96: 555 -
21b
Balkenhohl R.Bussche-Hunnefeld CVD.Lansky A.Zechel C. Angew. Chem. Int. Ed. 1996, 35: 2288 -
21c
Baldino CM. J. Comb. Chem. 2000, 2: 89 - 22
Thomsen I.Clausen K.Scheibye S.Lawesson S.-O. Org. Synth. Coll. Vol. VII John Wiley & Sons; London: 1990. p.372 - 23
Bowman WR.Heaney H.Jordan BM. Tetrahedron 1991, 47: 10119 - 24
Bookser BC.Zhu S. J. Comb. Chem. 2001, 3: 205 - 26
Deegan TL.Gooding OW.Baudart S.Porco JA. Tetrahedron Lett. 1997, 38: 4973
References
The material loss, as indicated by crude yields in Table [1] , was mainly due to the binding of the product to the resin. In order to keep the same method as used in the final library synthesis, we did not use excessive solvent, which was limited by the volume of the collection plate, to wash the resin to improve the yields