Abstract
An efficient synthetic method is reported in which 2-arylbenzoxazoles have been prepared in good to excellent yields under mild reaction conditions by the palladium-catalysed carbonylation of diaryliodonium salts with o-aminophenols followed by dehydrative cyclisation.
References
1.
Campbell M.M.
, Comprehensive Organic Chemisity , ed by
Sammes P.G.
; Pergamon Press , Oxford , 1979 , vol. 4 , p. 962 .
2.
(a)
Elderfield R.C.
, Ed. In Heterocyclic Compounds ; John Wiley & Sons : New York , 1957 , Vol. 5 . p 422 .
3.
Yalcin I.
,
Sener E.
,
Ozden T.
,
Ozden S.
, and
Akin A.
, Eur. J. Med. Chem. , 1990 , 25 , 705 .
4.
Fomum Z.T.
,
Landor P. D.
,
Landor S. R.
, and
Mpango G. B.
, Tetrahedron Lett. , 1975 , 16 , 1101 .
5.
So Y.-H.
, and
DeCaire R.
, Synth. Commun. , 1998 , 28 , 4123 .
6.
(a)
Stephens F.F.
, and
Bower J. D.
, J. Chem. Soc. , 1949 , 2971 .
7.
Stephens F.F.
, and
Bower J. D.
, J. Chem. Soc. , 1950 , 1723 .
8.
(a)
Nakagava K.
,
Onoue H.
, and
Sugita J.
, Chem. Pharm. Bull. (Japan), 1964 , 12 , 1135 . CA : 1965, 62 , 541.
9.
George M.V.
, and
Balachandran K. S.
, Chem. Rev. , 1975 , 75 , 491 .
10.
Bhathnagar I.
, and
George M. V.
, Tetrahedron , 1968 , 24 , 1293 .
11.
Srivastava R.G.
, and
Venkataramani P. S.
, Synth. Commun. , 1988 , 18 , 1537 .
12.
Varma R.S.
,
Saini R. K.
, and
Prakash O.
, Tetrahedron Lett. , 1997 , 38 , 2621 .
13.
Speier G.
, J. Mol. Catal. , 1987 , 41 , 253 .
14.
Grellmann K.H.
, and
Tauer Erich
, J. Am. Chem. Soc. , 1973 , 95 , 3104 .
15.
Perry R.J.
,
Wilson B. D.
, and
Miller R. J.
, J. Org. Chem. , 1992 , 57 , 2883 .
16.
Hideg K.
, and
Hankovszky H. O.
, Tetrahedron Lett. , 1965 , 6 , 2365
17.
Parrini Valerio
, Ann. Chim. (Rome), 1957 , 47 , 1347 .
18.
Horner Leopold
, and
Steppan Hartmut
, Ann. , 1957 , 606 , 24 . CA: 52 , 286b.
19.
Somayajulu V.V.
, and
Subba Rao N. V.
, Proc. Indian Acad. Sci. Sect. A, 1964 , 59 (6 ), 396 ; CA: 1965, 62 , 1639g.
20.
Siegrist A.E.
, Helv. Chim. Acta. , 1967 , 50 (3 ), 906 .
21.
Belyaev E. Yu.
,
Kondrat'eva L. E.
,
Shakhov N. A.
, Khim. Geterosikl. Soedin. , 1972 , (1 ), 10 .
22.
Hein D.W.
,
Alheim R. J.
, and
Leavitt J. J.
, J. Am. Chem. Soc. , 1957 , 79 , 427 .