RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
Synthesis 2008(24): 3974-3980
DOI: 10.1055/s-0028-1083245
DOI: 10.1055/s-0028-1083245
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Copper(I) Iodide Catalyzed Domino Process to Quinazolin-4(3H)-ones
Weitere Informationen
Received
22 August 2008
Publikationsdatum:
01. Dezember 2008 (online)
Publikationsverlauf
Publikationsdatum:
01. Dezember 2008 (online)
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
- 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
References
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].