A Practical Method for O-Acylation of N-Hydroxythiazole-2(3H)-thiones

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).

anhydride - acyl chloride - carbon radical - thiazolethione - thiohydroxamic acid

References

<A NAME="RT14609SS-1">1</A> Barton DHR. Crich D. Motherwell WB. J. Chem. Soc., Chem. Commun.  1983,  939 

<A NAME="RT14609SS-2">2</A> Motherwell WB. Imboden C. In Radicals in Organic Synthesis   Vol. 1:  Renaud P. Sibi MP. Wiley-VCH; Weinheim: 2001.  p.109-134  

<A NAME="RT14609SS-3">3</A> Crich D. Quintero L. Chem. Rev.  1989,  89:  1413 

<A NAME="RT14609SS-4">4</A> Shaw E. J. Am. Chem. Soc.  1949,  71:  67 

<A NAME="RT14609SS-5">5</A> Schneiders N. Gottwald T. Hartung J. Eur. J. Org. Chem.  2009,  799 

<A NAME="RT14609SS-6">6</A> Barton DHR. Blundell P. Jaszberenyi JCs. J. Am. Chem. Soc.  1991,  113:  6937 

<A NAME="RT14609SS-7">7</A> Theodorakis EA. Xiang X. Lee M. Gibson T. Tetrahedron Lett.  1998,  39:  3383 

<A NAME="RT14609SS-8">8</A> Castagnino E. Cangiotti M. Tongiani S. Ottaviani MF. J. Controlled Release  2005,  108:  215 

<A NAME="RT14609SS-9">9</A> Barton DHR. Parekh SI. In Half a Century of Free Radical Chemistry   Cambridge University Press; Cambridge: 1993.  Chap. 5. p.46-90  

<A NAME="RT14609SS-10">10</A> Garner P. Anderson JT. Dey S. J. Org. Chem.  1998,  63:  5732 

<A NAME="RT14609SS-11">11</A> Hartung J. Schur C. Kempter I. Altermann S. Stapf G. Bergsträßer U. Gottwald T. Heubes M. Tetrahedron  2009,  65:  7527 

<A NAME="RT14609SS-12">12</A> Barton DHR. Crich D. Kretschmar G. J. Chem. Soc., Perkin Trans. 1  1986,  39 

<A NAME="RT14609SS-13">13</A> Hartung J. Schwarz M. Svoboda I. Fueß H. Duarte M.-T. Eur. J. Org. Chem.  1999,  1275 

<A NAME="RT14609SS-14">14</A> Hartung J. Schwarz M. Synlett  2000,  371 

<A NAME="RT14609SS-15">15</A> Hartung J. Schwarz M. Org. Synth. Coll. Vol. 10   Wiley; New York: 2004.  p.437-441  

<A NAME="RT14609SS-16">16</A> Gross A. Schneiders N. Daniel K. Gottwald T. Hartung J. Tetrahedron  2008,  64:  10882 

<A NAME="RT14609SS-17">17</A> Hartung J. Altermann S. Svoboda I. Fuess H. Acta Crystallogr., Sect. E  2005,  61:  o1738 

<A NAME="RT14609SS-18">18</A> Chimiak A. Pryzchodzen W. Rachon J. Heteroat. Chem.  2002,  13:  169 

<A NAME="RT14609SS-19">19</A> Barton DHR. Lacher B. Zard SZ. Tetrahedron  1987,  43:  4321 

<A NAME="RT14609SS-20">20</A> Giese B. Stellmach J. Chem. Ber.  1980,  113:  3294 

<A NAME="RT14609SS-21">21</A> Perrin D. D. Armarego W. L. F. Perrin D. R. Purification of Laboratory Chemicals   2nd ed.. Pergamon Press; Oxford: 1980. 

<A NAME="RT14609SS-22">22</A> Midgley G. Thomas CB. J. Chem. Soc., Perkin Trans. 2  1987,  1103 

<A NAME="RT14609SS-23">23</A> Wang M.-X. Feng . G Q. J. Org. Chem.  2003,  68:  621