Synthesis, Inhaltsverzeichnis PSP © Georg Thieme Verlag Stuttgart ˙ New York A Practical Method for O-Acylation of N-Hydroxythiazole-2(3H)-thiones Christine Schur, Andreas Groß, Jens Hartung*Fachbereich Chemie, Organische Chemie, Technische Universität Kaiserslautern, Erwin-Schrödinger-Straße, 67663 Kaiserslautern, GermanyFax: +49(631)2053921; e-Mail: hartung@chemie.uni-kl.de; Artikel empfehlen Abstract Artikel einzeln kaufen Alle Artikel dieser Rubrik Abstract O-Acylation of 4- and 4,5-substituted N-hydroxythiazole-2(3H)-thiones occurred in solutions of acetone upon treatment with solid K2CO3 and a variety of neat acyl chlorides (primary, secondary, and tertiary alkyl, aryl; 60-87% yield; ∼10 g scale). Key words anhydride - acyl chloride - carbon radical - thiazolethione - thiohydroxamic acid Volltext Referenzen References 1 Barton DHR. Crich D. Motherwell WB. J. Chem. Soc., Chem. Commun. 1983, 939 2 Motherwell WB. Imboden C. In Radicals in Organic Synthesis Vol. 1: Renaud P. Sibi MP. Wiley-VCH; Weinheim: 2001. p.109-134 3 Crich D. Quintero L. Chem. Rev. 1989, 89: 1413 4 Shaw E. J. Am. Chem. Soc. 1949, 71: 67 5 Schneiders N. Gottwald T. Hartung J. Eur. J. Org. Chem. 2009, 799 6 Barton DHR. Blundell P. Jaszberenyi JCs. J. Am. Chem. Soc. 1991, 113: 6937 7 Theodorakis EA. Xiang X. Lee M. Gibson T. Tetrahedron Lett. 1998, 39: 3383 8 Castagnino E. Cangiotti M. Tongiani S. Ottaviani MF. J. Controlled Release 2005, 108: 215 9 Barton DHR. Parekh SI. In Half a Century of Free Radical Chemistry Cambridge University Press; Cambridge: 1993. Chap. 5. p.46-90 10 Garner P. Anderson JT. Dey S. J. Org. Chem. 1998, 63: 5732 11 Hartung J. Schur C. Kempter I. Altermann S. Stapf G. Bergsträßer U. Gottwald T. Heubes M. Tetrahedron 2009, 65: 7527 12 Barton DHR. Crich D. Kretschmar G. J. Chem. Soc., Perkin Trans. 1 1986, 39 13 Hartung J. Schwarz M. Svoboda I. Fueß H. Duarte M.-T. Eur. J. Org. Chem. 1999, 1275 14 Hartung J. Schwarz M. Synlett 2000, 371 15 Hartung J. Schwarz M. Org. Synth. Coll. Vol. 10 Wiley; New York: 2004. p.437-441 16 Gross A. Schneiders N. Daniel K. Gottwald T. Hartung J. Tetrahedron 2008, 64: 10882 17 Hartung J. Altermann S. Svoboda I. Fuess H. Acta Crystallogr., Sect. E 2005, 61: o1738 18 Chimiak A. Pryzchodzen W. Rachon J. Heteroat. Chem. 2002, 13: 169 19 Barton DHR. Lacher B. Zard SZ. Tetrahedron 1987, 43: 4321 20 Giese B. Stellmach J. Chem. Ber. 1980, 113: 3294 21 Perrin D. D. Armarego W. L. F. Perrin D. R. Purification of Laboratory Chemicals 2nd ed.. Pergamon Press; Oxford: 1980. 22 Midgley G. Thomas CB. J. Chem. Soc., Perkin Trans. 2 1987, 1103 23 Wang M.-X. Feng . G Q. J. Org. Chem. 2003, 68: 621
