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 2010(3): 538-542
DOI: 10.1055/s-0029-1217102
DOI: 10.1055/s-0029-1217102
PSP
© Georg Thieme Verlag
Stuttgart ˙ New York
A Practical Method for O-Acylation of N-Hydroxythiazole-2(3H)-thiones
Further Information
Received
24 July 2009
Publication Date:
06 November 2009 (online)
Publication History
Publication Date:
06 November 2009 (online)
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
- 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