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Synthesis 2005(18): 3059-3062
DOI: 10.1055/s-2005-918419
DOI: 10.1055/s-2005-918419
PAPER
© Georg Thieme Verlag Stuttgart · New York
A Convenient Route to Biologically Important Quinazolines Using N-Arylamino-1,3-diazabuta-1,3-dienes
Further Information
Received
11 April 2005
Publication Date:
06 October 2005 (online)
Publication History
Publication Date:
06 October 2005 (online)

Abstract
A potential and convenient protocol for the synthesis of 4-arylquinazolines and 4-aminoquinazolines by electrocyclisation of N-arylamino-1,3-diazabuta-1,3-dienes is described.
Key words
quinazolines - electrocyclisation - N-arylamino-1,3-diazabuta-1,3-dienes - intramolecular H-bonding - amino-substituted quinazolines
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1a
Brown DJ. Quinazoline: The Chemistry of Heterocyclic Compounds Vol 55: John Wiley and Sons; Chichester UK: 1996. Supplement I. -
1b
Jones P.Chambers M. Tetrahedron 2003, 58: 9973 -
1c
Webb TR.Lvovskiy D.Kim SA.Ji X.Melman M.Lindeu J.Jacobson KA. Bioorg. Med. Chem. 2003, 11: 77 -
1d
Michael JP. Nat. Prod. Rep. 2002, 742 -
1e
Frère S.Thiéry V.Bailly C.Besson T. Tetrahedron 2003, 59: 773 -
2a
Billimmoria AD.Cava MP. J. Org. Chem. 1994, 59: 6772 -
2b
Blackman A.Hambley TM.Picker R.Taylor WC.Thirasana N. Tetrahedron Lett. 1987, 28: 5561 - 3
Kunes J.Bazant J.Pour M.Waisser K.Slosarek M.Janota J. Farmaco 2000, 55: 725 - 4
El-Sherbeny MA.Gineinah MM.Nasr MN.El-Shafeih FS. Arzneim.-Forsch. 2003, 53: 206 - 5
Khalil AA.Abdel-Hamid SG.Al-Obaid AM.El-Subbag HI. Arch. Pharm. (Weinheim, Ger.) 2003, 336: 95 - 6
Malecki N.Caroto P.Rigo B.Goossens JF.Houssin R.Bailly C.Henichart JP. Bioorg. Med. Chem. 2004, 12: 641 - 7
Bertelli L.Biagi G.Giorgi I.Livi O.Manera C.Scartoni V.Lucacchini A.Giannaccini G.Barili PL. Eur. J. Med. Chem. 2000, 35: 333 -
8a
Orfi L.Waczek F.Pato J.Varga I.Hegymegi-Barakonyi B.Houghten RA.Keri G. Curr. Med. Chem. 2004, 11: 2549 -
8b
Fry DW.Kraker AJ.McMichael A.Ambroso LA.Nelson JM.Leopold WR.Connors RW.Bridges AJ. Science 1994, 265: 1093 - 9
Oishi A.Yasumoto M.Goto M.Tsuchiya T.Shibuya I.Taguchi Y. Heterocycles 1994, 38: 2073 - 10
Shi D.Wang J.Shi C.Rong L.Zhuang Q.Hu H. Synlett 2004, 1098 -
11a
Rossi E.Stradi R.Visentin P. Tetrahedron 1990, 46: 3581 -
11b
Rossi E.Stradi R.Clenantano G.Strada A. Tetrahedron Lett. 1990, 31: 903 - 12
Kumar V.Sharma AK.Mahajan MP. Synth. Commun. 2004, 34: 49 - 13
Kumar V.Mohan C.Gupta M.Mahajan MP. Tetrahedron 2004, 61: 3533 - 14
Bedi PM.Kumar V.Mahajan MP. Bioorg. Med. Chem. Lett. 2004, 14: 5211 - 15
Goel RK.Kumar V.Mahajan MP. Bioorg. Med. Chem. Lett., in press -
16a
Jayakumar S.Ishar MPS.Mahajan MP. Tetrahedron 2002, 58: 379 -
16b
Mazumdar SN.Ibnusaud I.Mahajan MP. Tetrahedron Lett. 1987, 28: 2641 -
16c
Mazumdar SN.Mahajan MP. Tetrahedron 1991, 47: 1473 -
16d
Mazumdar SN.Mukherjee S.Sharma AK.Sengupta D.Mahajan MP. Tetrahedron 1994, 50: 7579 -
16e
Mukherjee S.Mazumdar SN.Sharma AK.Mahajan MP. Heterocycles 1998, 47: 933 -
16f
Dey PD.Sharma AK.Bharatam PV.Mahajan MP. Tetrahedron 1997, 53: 13829 - 17
Dey S.Ramachandra M.Pastan I.Gottesman MM.Ambudkar SV. Proc. Natl. Acad. Sci. U.S.A. 1997, 94: 10594 -
18a
Sharma AK.Mahajan MP. Tetrahedron Lett. 1986, 27: 5875 -
18b
Mazumdar SN.Mahajan MP. Synthesis 1990, 417 -
18c
Dey PD.Sharma AK.Bhartam PV.Mahajan MP. Tetrahedron 1997, 53: 13829 -
18d
Dey PD.Sharma AK.Rai SN.Mahajan MP. Tetrahedron 1995, 51: 7459