Abstract
An efficient synthesis of substituted quinazolin-4(3H )-ones by a one-pot ligand-free CuI-catalyzed
coupling/condensative cyclization under mild conditions
is described. Our study provides an alternative strategy for the
preparation of biologically active quinazolin-4(3H )-ones.
Key words
quinazolin-4(3H )-ones - one-pot - ligand-free - copper(I) iodide - coupling/condensative
cyclization
References
1
Shcherbakova I.
Balandrin MF.
Fox J.
Ghatak A.
Heaton WL.
Conklin RL.
Bioorg. Med. Chem.
Lett.
2005,
15:
1557
2a
Jonson M.
Li A.-R.
Liu J.
Fu Z.
Zhu L.
Miao S.
Wang X.
Xu Q.
Huang A.
Marcus A.
Xu F.
Ebsworth K.
Sablan E.
Danao J.
Kumer J.
Dairaghi D.
Lawrence C.
Sullivan T.
Tonn G.
Schall T.
Collins T.
Medina J.
Bioorg. Med. Chem. Lett.
2007,
17:
3339
2b
Walser TC.
Rifat S.
Ma X.
Kundu N.
Ward C.
Goloubeva O.
Johnson MG.
Medina JC.
Collins TL.
Fulton AM.
Cancer Res.
2006,
66:
7701
3a
Skelton LA.
Ormerod MG.
Titley J.
Kimbell R.
Brunton LA.
Jackman AL.
Br. J. Cancer
1999,
79:
1692
3b
Bavetsias V.
Skelton LA.
Yafai F.
Mitchell F.
Wilson SC.
Allan B.
Jackman AL.
J.
Med. Chem.
2002,
45:
3692
4
Rudolph J.
Esler WP.
O’Connor S.
Coish PDG.
Wickens PL.
Brands M.
Bierer DE.
Bloomquist BT.
Bondar G.
Chen L.
Chuang C.-Y.
Claus TH.
Fathi Z.
Fu W.
Khire UR.
Kristie JA.
Liu X.-G.
Lowe DB.
McClure AC.
Michaels M.
Ortis AA.
Ramsden PD.
Schoenleber RW.
Shelekhin TE.
Vakalopoulos A.
Tang W.
Wang L.
Yi L.
Gardell SJ.
Livingston JN.
Sweet LJ.
Bullock WH.
J.
Med. Chem.
2007,
50:
5202
5
Jiao RH.
Xu S.
Liu JY.
Ge HM.
Ding H.
Xu C.
Zhu HL.
Tan RX.
Org. Lett.
2006,
8:
5709
For selected examples of recent
syntheses of rutaecarpine, see:
6a
Mohanta PK.
Kim K.
Tetrahedron
Lett.
2002,
43:
3993
6b
Mhaske SB.
Argade NP.
Tetrahedron
2004,
60:
3417
6c
Harayama T.
Hori A.
Serban G.
Morikami Y.
Matsumoto T.
Abe H.
Takeuchi Y.
Tetrahedron
2004,
60:
10645
6d
Chavan SP.
Sivappa R.
Tetrahedron Lett.
2004,
45:
997
6e
Zhang C.
De C K.
Mal R.
Seidel D.
J. Am. Chem. Soc.
2008,
130:
416 ; and references cited therein
7
Chandregowda V.
Rao Gudapati V.
Reddy Goukanapalli C.
Org. Process Res. Dev.
2007,
11:
813
For examples, see:
8a
Gungor T.
Chen Y.
Golla R.
Ma Z.
Corte JR.
Northrop JP.
Bin B.
Dickson JK.
Stouch T.
Zhou R.
Iohnson SE.
Seethala R.
Feyen JHM.
J.
Med. Chem.
2006,
49:
2440
8b
Vinodkumar R.
Chari MA.
Dubey PK.
J.
Heterocycl. Chem.
2007,
44:
1537
8c
Jatav V.
Mishra P.
Kashaw S.
Stables JP.
Eur. J. Med. Chem.
2008,
43:
135
8d
Liu J.
Lee J.
Dalton AM.
Bi G.
Yu L.
Baldino CM.
McElory E.
Brown M.
Tetrahedron Lett.
2005,
46:
1241
For examples, see:
9a
Snider BB.
Zeng H.
J. Org. Chem.
2003,
68:
545
9b
Skibo EB.
Huang X.
Martinez R.
Lemus RH.
Craigo WA.
Dorr RT.
J.
Med. Chem.
2002,
45:
5543
9c
Kende AS.
Fan J.
Chen Z.
Org.
Lett.
2003,
5:
3205
9d
Jeong JU.
Chen X.
Rahman A.
Yamashita DS.
Luengo JI.
Org. Lett.
2004,
6:
1013
9e
Twin H.
Batey RA.
Org. Lett.
2004,
6:
4913
9f
Walker SJ.
Hart DJ.
Tetrahedron
Lett.
2007,
48:
6214
9g
Fuwa H.
Kobayashi T.
Tokitoh T.
Torii Y.
Natsugari H.
Synlett
2004,
2497
9h
Kshirsagar UA.
Mhaske SB.
Argade NP.
Tetrahedron Lett.
2007,
48:
3243
9i
Fuwa H.
Kobayashi T.
Tokitoh T.
Torii Y.
Natsugari H.
Tetrahedron
2005,
61:
4297
9j
Alexandre F.
Berecibar A.
Besson T.
Tetrahedron
Lett.
2002,
43:
3911
For recent studies on the synthesis
of N-heterocycles through Ullmann-type couplings, see:
10a
Zou B.
Yuan Q.
Ma D.
Org.
Lett.
2007,
9:
4291
10b
Zou B.
Yuan Q.
Ma D.
Angew.
Chem. Int. Ed.
2007,
46:
2598
10c
Lu B.
Ma D.
Org. Lett.
2006,
8:
6115
10d
Evindar G.
Batey RA.
Org. Lett.
2003,
5:
133
10e
Altenhoff G.
Glorius F.
Adv. Synth. Catal.
2004,
346:
1661
10f
Klapars A.
Parris S.
Anderson KW.
Buchwald SL.
J. Am. Chem. Soc.
2004,
126:
3529
10g
Yang T.
Lin C.
Fu H.
Jiang Y.
Zhao Y.
Org. Lett.
2005,
7:
4781
10h
Evindar G.
Batey RA.
J. Org. Chem.
2006,
71:
1802
10i
Martin R.
Rodríguez R.
Buchwald SL.
Angew. Chem. Int. Ed.
2006,
45:
7079
10j
Rivero MR.
Buchwald SL.
Org.
Lett.
2007,
9:
973
10k
Yuan X.
Xu X.
Zhou X.
Yuan J.
Mai L.
Li Y.
J. Org.
Chem.
2007,
72:
1510
11a
Guillaume M.
Org. Process Res. Dev.
2006,
10:
1227
11b
Ma D.
Cai Q.
Zhang H.
Org.
Lett.
2003,
5:
2453
12 CCDC # 701749 contains the
supplementary crystallographic data for this paper. These data can
be obtained free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html [or
from the Cambridge Crystallographic Data Centre, 12, Union Road,
Cambridge CB2 1EZ, UK; fax: +44(1223)336033; E-mail: deposit@ccdc.cam.ac.uk].