Abstract
An efficient procedure for the synthesis of benzoxazoles by the heteroannulation of nitriles and o-aminophenols in the presence of a catalytic amount of copper(II) trifluoromethanesulfonate, has been developed. This method represents a practical and attractive alternative for the synthesis of both 2-arylbenzoxazoles and 2-alkylbenzoxazoles.
References
1.
Don M.-J.
,
Shen C.-C.
,
Lin Y.-L.
,
Syu W.J.
,
Ding Y.-H.
, and
Sun C.-M.
, J. Nat. Prod. , 2005 , 68 , 1066 .
2.
Viirre R.D.
,
Evindar G.
, and
Batey R.A.
, J. Org. Chem. , 2008 , 73 , 345 .
3.
Deluca M.R.
, and
Kerwin S.M.
, Tetrahedron Lett. , 1997 , 38 , 199 .
4.
Sato Y.
,
Yamada M.
,
Yoshida S.
,
Soneda T.
,
Ishikawa M.
,
Nizato T.
,
Suzuki K.
, and
Konno F.
, J. Med. Chem. , 1998 , 41 , 3015 .
5.
Temis O.
,
Oren I.
,
Sener E.
,
Yalcin I.
, and
Ucarturk N.
, Farmaco , 1998 , 53 , 337 .
6.
Sato S.
,
Kajiura T.
,
Noguchi M.
,
Takehana K.
,
Kobayashi T.
, and
Tsuji T.J.
, Antibiot. , 2001 , 54 , 102 .
7.
Gong B.Q.
,
Hong F.
,
Kohm C.
,
Bonham L.
, and
Klein P.
, Bioorg. Med. Chem. Lett. , 2004 , 14 , 1455 .
8.
Chancellor D.R.
,
Davies K.E.
,
Moor O.D.
,
Dorgan C.R.
,
Johnson P.D.
,
Lambert A.G.
,
Lawrence D.
,
Lecci C.
,
Maillol C.
,
Middleton P.J.
,
Nugent G.
,
Poignant S.D.
,
Potter A.C.
,
Price P.D.
,
Pye R.J.
,
Storer R.
,
Tinsley J.M.
,
van Well R.
,
Vickers R.
,
Vile J.
,
Wilkes F.J.
,
Wilson F.X.
,
Wren S.P.
, and
Wynne G.M.
, J. Med. Chem. , 2011 , 54 , 3241 .
9.
Heathcock C.H.
, Comprehensive organic synthesis , eds
Trost B.M.
, and
Fleming I.
, Pergamon Press , New York , 1991 , Vol. 2 .
10.
Reser A.
,
Leyshon L.J.
,
Saunders D.
,
Mijovic M.V.
,
Bright A.
, and
Brogie J.
, J. Am. Chem. Soc. , 1972 , 94 , 2444 .
11.
Kanegae Y.
,
Peariso K.
, and
Martinez S.S.
, Appl. Spectrosc. , 1996 , 50 , 316 .
12.
Hölljes E.L.J.
, and
Wagner E.C.
, J. Org. Chem. , 1944 , 9 , 31 .
13.
Hein D.W.
,
Alheim R.J.
, and
Leavitt J.J.
, J. Am. Chem. Soc. , 1957 , 79 , 4273 .
14.
Pottorf R.S.
,
Chadha N.K.
,
Katkevics M.
,
Ozola V.
,
Suna E.
,
Ghane H.
,
Regberg T.
, and
Player M.R.
, Tetrahedron Lett. , 2003 , 44 , 175 .
15.
Kawashita Y.
,
Nakamichi N.
,
Kawabata H.
, and
Hayashi M.
, Org. Lett. , 2003 , 5 , 3713 .
16.
Evindar G.
, and
Batey R.A.
, J. Org. Chem. , 2006 , 71 , 1802 .
17.
Seijas J.A.
,
Vázquez-Tato M.P.
,
Carballido-Reboredo M.R.
,
Crecente-Campo J.
, and
Romar-López L.
, Synlett. , 2007 , 313 .
18.
Chen Y.X.
,
Qian L.F.
,
Zhang W.
, and
Han B.
, Angew. Chem. Int. Ed. , 2008 , 47 , 9330 .
19.
Viirre R.D.
,
Evindar G.
, and
Batey R.A.
, J. Org. Chem. , 2008 , 73 , 3452 .
20.
Bonnamour J.
, and
Bolm C.
, Org. Lett. , 2008 , 10 , 2665 .
21.
Blacker A.J.
,
Farah M.M.
,
Hall M.I.
,
Marsden S.P.
,
Saidi O.
, and
Williams J.M.J.
, Org. Lett. , 2009 , 11 , 2039 .
22.
Hassan Z.B.
, and
Khadijeh H.N.
, Eur. J. Org. Chem. , 2009 , 29 , 4926 .
23.
Qiao J.X.
,
Wang T.C.
,
Hu C.
,
Li J.Q.
,
Wexler R.R.
, and
Lam P.Y.S.
, Org. Lett. , 2011 , 13 , 1804 .
24.
Guru M.M.
,
Ali M.A.
, and
Punniyamurthy T.
, Org. Lett. , 2011 , 13 , 1194 .
25.
Guru M.M.
,
Ali M.A.
, and
Punniyamurthy T.
, J. Org. Chem. , 2011 , 76 , 5295 .
26.
Yoo W.-J.
,
Yuan H.
,
Miyamura H.
, and
Kobayashi S.
, Adv. Synth. Catal. , 2011 , 353 , 3085 .
27.
Chen C.-Y.
,
Andreani T.
, and
Li H.
, Org. Lett. , 2011 , 13 , 6300 .
28.
Peng J.
,
Zong C.
,
Ye M.
,
Chen T.
,
Gao D.
,
Wang Y.
, and
Chen C.
, Org. Biomol. Chem. , 2011 , 9 , 1225 .
29.
Xu Y.L.
,
Pan Y.M.
,
Wu Q.
,
Wang H.S.
, and
Liu P.Z.
, J. Org. Chem. , 2011 , 76 , 8472 .
30.
Kukushkin V.Y.
, and
Pombeiro A.J.L.
, Chem. Rev. , 2002 , 102 , 1771 .
31.
Yang F.-Z.
,
Xu Z.-Q.
,
Wang Z.
,
Yu Z.-K.
, and
Wang R.
, Chem. Eur. J. , 2011 , 17 , 6321 .
32.
Roger J.
,
Verrier C.
,
Le Goff R.
,
Hoarau C.
, and
Doucet H.
, ChemSusChem. , 2009 , 2 , 951 .
33.
Besselievre F.
,
Piguel S.
,
Mahuteau-Betzer F.
, and
Grierson D.S.
, Org. Lett. , 2008 , 10 , 4029 .
34.
Xing R.-G.
,
Li Y.-N.
,
Liu Q.
,
Meng Q.-Y.
,
Li J.
,
Shen X.-X.
,
Liu Zh.-G.
,
Zhou B.
,
Yao X.-J.
, and
Liu Z.-L.
, Eur. J. Org. Chem. , 2010 , 6627 .
35.
Ackermann L.
,
Barfuesser S.
,
Kornhaass C.
,
Kapdi A.R.
, Org. Lett. , 2011 , 13 , 3082 .
36.
Peng J.-S.
,
Zong C.-J.
,
Ye M.
,
Chen T.-H.
,
Gao D.-W.
,
Wang Y.-F.
, and
Chen C.-X.
, Org. Biomol. Chem. , 2011 , 9 , 1225 .