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Synthesis 2011(22): 3649-3660
DOI: 10.1055/s-0030-1260259
DOI: 10.1055/s-0030-1260259
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Thiohydantoins: Selective N- and S-Functionalization for Liebeskind-Srogl Reaction Study
Weitere Informationen
Received
25 July 2011
Publikationsdatum:
10. Oktober 2011 (online)
Publikationsverlauf
Publikationsdatum:
10. Oktober 2011 (online)
![](https://www.thieme-connect.de/media/synthesis/201122/lookinside/thumbnails/10.1055-s-0030-1260259-1.jpg)
Abstract
Thiohydantoins formed by the Schlack-Kumpf protocol were selectively functionalized at the nitrogen, sulfur, or carbon atom to test the Liebeskind-Srogl reaction possibilities.
Key words
heterocycles - palladium - cross-coupling - amino acids - sulfur
-
1a
Ware E. Chem. Rev. 1950, 46: 403 -
1b
Edman P.Begg G. Eur. J. Biochem. 1967, 1: 80 -
2a
Duggan BM.Laslett RL.Wilshire JFK. Aust. J. Chem. 1996, 49: 541 -
2b
Johnson TB.Nicolet BH. J. Am. Chem. Soc. 1911, 33: 1973 -
2c
Thielemann H. Z. Chem. 1978, 18: 174 -
2d
Villemin D.Ricard M. Synth. Commun. 1987, 17: 283 -
2e
Marton J.Enisz J.Hosztafi S.Timar T. J. Agric. Food Chem. 1993, 41: 148 -
2f
Davis RA.Aalbersberg W.Meo S.Moreira da Rocha R.Ireland CM. Tetrahedron 2002, 58: 3263 -
3a
Bentarzi Y.Nedjar-Kolli B.Plas A.Chalard P.Troin Y. ARKIVOC 2010, (x): 328 -
3b
Jullian M.Hernandez A.Maurras A.Puget K.Amblard M.Martinez J.Subra G. Tetrahedron Lett. 2009, 50: 260 -
3c
Lanman BA.Overman LE. Heterocycles 2006, 70: 557 - 4
Wang ZD.Sheikh SO.Zhang Y. Molecules 2006, 11: 739 -
5a
Yoshino H.Sato H.Shiraishi T.Tachibana K.Emura T.Honma A.Ishikura N.Tsunenari T.Watanabe M.Nishimoto A.Nakamura R.Nakagawa T.Ohta M.Takata N.Furumoto K.Kimura K.Kawata H. Bioorg. Med. Chem. 2010, 18: 8150 -
5b
Thanusu J.Kanagarajan V.Gopalakrishnan M. Bioorg. Med. Chem. Lett. 2010, 20: 713 -
5c
Raghuvanshi DS.Singh KN. Phosphorus, Sulfur Silicon Relat. Elem. 2010, 185: 2243 - 6
Wang X.-J.Zhang L.Xu Y.Krishnamurthy D.Varsolona R.Nummy L.Shen S.Frutos RP.Byrne D.Chung JC. Tetrahedron Lett. 2005, 46: 273 - 7
Rajamaki S.Innitzer A.Falciani C.Tintori C.Christ F.Witvrouw M.Debyser Z.Massa S.Botta M. Bioorg. Med. Chem. Lett. 2009, 19: 3615 -
8a
Gasch C.Illangua JM.Merino-Montiel P.Fuentes J. Tetrahedron 2009, 65: 4149 -
8b
Aguilar-Moncayo M.Ortiz Mellet C.Garcia Fernandez JM.Garcia-Moreno MI. J. Org. Chem. 2009, 74: 3595 -
8c
Fuentes J.Salameh BAB.Angeles Pradera M.Fernández de Córdoba FJ.Gasch C. Tetrahedron 2006, 62: 97 -
9a
Kumar R.Chauhan PMS. Tetrahedron Lett. 2008, 49: 5475 -
9b
Gao F.Zhang G.Zhang S.Cheng Y.Shi Z.Li Y.Gao J. Tetrahedron 2007, 63: 3973 -
9c
El-Barbary AA.El-Ezz AZA.Sharaf AM.Nielsen C. Phosphorus, Sulfur Silicon Relat. Elem. 2007, 182: 1621 -
9d
Boulos L.Yakout E.-S.Arsanious M. Phosphorus, Sulfur Silicon Relat. Elem. 2006, 181: 1615 -
9e
Chérouvrier J.-R.Carreaux F.Bazureau JP. Molecules 2004, 9: 867 - 10
Reyes S.Burgess K. J. Org. Chem. 2006, 71: 2507 - 11
Lee S.Rosazza JPN. Org. Lett. 2004, 6: 365 - 12
Girniene J.Tatibouët A.Šačkus A.Yang J.Holman GD.Rollin P. Carbohydr. Res. 2003, 338: 711 -
13a
Prokopcov H.Kappe CO. Angew. Chem. Int. Ed. 2008, 47: 2 -
13b
Dandepally SR.Williams AL. Tetrahedron Lett. 2010, 51: 5753 -
13c
Musaev DG.Liebeskind LS. Organometallics 2009, 28: 4639 -
14a
Silva S.Tardy S.Routier S.Suzenet F.Tatibouët A.Rauter AP.Rollin P. Tetrahedron Lett. 2008, 49: 5583 -
14b
Silva S.Sylla B.Suzenet F.Tatibouët A.Rauter AP.Rollin P. Org. Lett. 2008, 10: 853 -
14c
Leconte N.Pellegatti L.Tatibouët A.Suzenet F.Rollin P.Guillaumet G. Synthesis 2007, 857 - 15
Ates-Alagoz Z.Altanlar N.Buyukbingol E. J. Heterocycl. Chem. 2009, 46: 1375 - 16
Marton J.Enisz J.Hosztafi S.Timar T. J. Agric. Food Chem. 1993, 41: 148 - 17
Jakse R.Kroselj V.Recnik S.Sorsak G.Svete J.Stanovnik B.Grdadolnik SG. Z. Naturforsch., B 2002, 57: 453 - 18
Oumouch S.Bourotte M.Schmitt M.Bourguignon JJ. Synthesis 2005, 25 - 19
Arshad N.Hashim J.Kappe CO. J. Org. Chem. 2009, 74: 5118 -
20a
Savarin C.Srogl J.Liebeskind LS. Org. Lett. 2001, 3: 91 -
20b
Zhang S.Zhang D.Liebeskind LS. J. Org. Chem. 1997, 62: 2312 - 21
Swan JM. Aust. J. Chem. 1952, 4: 711 - 22
Wolfe DM.Schreiner PR. Synthesis 2007, 2002