Abstract
Thiophenes may be converted to substituted arenes by oxidative cycloaddition to alkynes or by oxidative cycloaddition to alkenes with subsequent oxidative SO-extrusion. Cyano- and acetylamino-groups do not interfere in the reaction and are stable under the reaction conditions. This transformation can be used as a novel route to non-natural aryl-containing amino acids.
References
1.
For a typical recent review, see:
Gelmi M.L.
, and
Pocar D.
, Org. Prep. Proc. Int. , 2003 , 35 , 141 .
2.
Chen L.
,
Tilley J. W.
,
Huang T.-N.
,
Miklowski D.
,
Trilles R.
,
Guthrie R. W.
,
Luk K.
,
Hanglow A.
,
Rowan K.
,
Schwinge V.
, and
Wolitzky B.
, Biol. Med. Chem. Lett. , 2000 , 10 , 725 .
3.
Meiwes J.
,
Schudok M.
, and
Kretschmar G. C.
, Tetrahedron Asymmetry , 1997 , 8 , 527 .
4.
Fleming S.A.
, Tetrahedron , 1995 , 51 , 12479 .
5.
Kayser B.
,
Altman J.
, and
Beck W.
, Tetrahedron , 1997 , 53 , 2475 .
6.
Naperstkow A.M.
,
Macaulay J. B.
,
Newlands M. J.
, and
Fallis A. G.
, Tetrahedron Lett. , 1989 , 30 , 5077 .
7.
Li Y.Q.
,
Thiemann T.
,
Sawada T.
, and
Tashiro M.
, J. Chem. Soc., Perkin Trans. 1 , 1994 , 2323 .
8.
Thiemann T.
,
Li Y. Q.
,
Mataka S.
, and
Tashiro M.
, J. Chem. Res. (S) , 1995 , 384 ; (M ), 1995, 2364.
9.
Cieplak A.S.
, J. Am. Chem. Soc. , 1981 , 103 , 4540 .
10.
For a review, see:
Cieplak A.S.
, Chem. Rev. , 1999 , 9 , 1265 .
