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DOI: 10.1055/s-0030-1260147
Synthesis of Quinoxaline Analogues
Publication History
Publication Date:
01 August 2011 (online)
Abstract
Substituted tricyclic or tetracyclic quinoxalines, tricyclic pyridoquinoxalines and bis-quinoxalines were synthesized in high yields starting from cyclic ketones by the α-bromination of cyclic ketones with N-bromosuccinimide (NBS) followed by condensation of the resulting α-bromo ketones with 1,2-diaminobenzene, 3,4-diaminopyridine, or 3,3′-diaminobenzidine.
Key words
condensation - halogenation - tandem reactions - heterocycles - arenes
- Supporting Information for this article is available online:
- Supporting Information
-
1a
Comprehensive Heterocyclic Chemistry II
Vol.
6:
Sato N.Katritzky AR.Rees CW.Scriven EFV. Pergamon Press; Oxford: 1996. p.233 -
1b
Seitz LE.Suling WJ.Reynolds RC. J. Med. Chem. 2002, 45: 5604 -
1c
Kamal A.Reddy KL.Devaiah V.Shankaraiah N.Rao MV. Mini-Rev. Med. Chem. 2006, 6: 71 -
1d
Chen Q.Bryant VC.Lopez H.Kelly DL.Luo X.Natarajan A. Bioorg. Med. Chem. Lett. 2011, 21: 1903 -
1e
You L.Cho EJ.Leavitt J.Ma L.-C.Montelione GT.Anslyn EV.Krug RM.Ellington A.Robertus JD. Bioorg. Med. Chem. Lett. 2011, 21: 3007 -
2a
Porter AEA. Comprehensive Heterocyclic Chemistry Pergamon; Oxford: 1984. -
2b
Brown DJ. The Chemistry of Heterocyclic Compounds John Wiley & Sons; New Jersey: 2004. - 3 For Bi(0), see:
Antoniotti S.Dunach E. Tetrahedron Lett. 2002, 43: 3971 - For PEG400, see:
-
4a
Cho CS.Ren WX.Shim SC. Tetrahedron Lett. 2007, 48: 4665 -
4b
Padmavathy K.Nagendrappa G.Geetha KV. Tetrahedron Lett. 2011, 52: 544 - For green chemistry, see:
-
5a
Huang T.Zhang Q.Chen J.Gao W.Ding J.Wu H. J. Chem. Res. 2009, 12: 761 -
5b
More SV.Sastry MNV.Yao C.-F. Green Chem. 2006, 8: 91 -
5c
Sarkis GY.Al-Azawe S. J. Chem. Eng. Data 1973, 18: 102 - For solid-phase chemistry, see:
-
6a
Wu Z.Ede NJ. Tetrahedron Lett. 2001, 42: 8115 -
6b
Singh SK.Gupta P.Duggineni S.Kundu B. Synlett 2003, 2147 -
6c
Das B.Venkateswarlu K.Suneel K.Majhi A. Tetrahedron Lett. 2007, 48: 5371 -
6d For solid-phase extraction,
see:
Kowalski JA.Leonard SF.Lee GE. J. Comb. Chem. 2006, 8: 774 - For microwave irradiation, see:
-
7a
Zhao Z.Wisnoski DD.Wolkenberg SE.Leister WH.Wang Y.Lindsley CW. Tetrahedron Lett. 2004, 45: 4873 -
7b
Xekoukoulotakis NP.Hadjiantoniou-Maroulis CP.Maroulis AJ. Tetrahedron Lett. 2000, 41: 10299 -
7c
Kim SY.Park KH.Chung YK. Chem. Commun. 2005, 1321 -
8a
Kim SY.Park KH.Chung YK. Chem. Commun. 2005, 1321 -
8b
Jeena V.Robinson RS. Beilstein J. Org. Chem. 2009, 5: 24 -
8c
Shaabani A.Maleki A. Chem. Pharm. Bull. 2008, 56: 79 -
8d
Slusarczyk M.de Borggraeve WM.Toppet S.Hoornaert GJ. Eur. J. Org. Chem. 2007, 2987 - For iodine, see:
-
9a
Bhosale RS.Sarda SR.Ardhapure SS.Jadhav WN.Bhusare SR.Pawar RP. Tetrahedron Lett. 2005, 46: 7183 -
9b
More SV.Sastry MNV.Wang C.-C.Yao C.-F. Tetrahedron Lett. 2005, 46: 6345 - 10 For sulfamic acid, see:
Darabi HR.Mohandessi S.Aghapoor K.Mohsenzadeh F. Catal. Commun. 2007, 8: 389 - 11 For Ni nanoparticles, see:
Kumar A.Kumar S.Saxena A.De A.Mozumdar S. Catal. Commun. 2008, 9: 778. - Tandem oxidation processes:
-
12a For Pd(OAc)2:
Robinson RS.Taylor RJK. Synlett 2005, 1003 -
12b For [RuCl2(PPh3)3]:
Cho CS.Oh SG. Tetrahedron Lett. 2006, 47: 5633 -
12c For HgI2:
Kotharkar SA.Shinde DB. Bull. Korean Chem. Soc. 2006, 27: 1466 -
12d For CuCl2:
Cho CS.Oh SG. J. Mol. Catal. A: Chem. 2007, 205 -
12e For [Ga(OTf)3]:
Cai JJ.Zou JP.Pan XQ.Zhang W. Tetrahedron Lett. 2008, 49: 7386 -
12f For MnO2:
Raw SA.Wilfred CD.Taylor RJK. Chem. Commun. 2003, 2286 -
13a
Venkatesh C.Singh B.Mahata PK.Ila H.Junjappa H. Org. Lett. 2005, 7: 2169 -
13b
da Silva MJ.Pinto MCFR.de Simone CA.Soares JG.Reys JRM.Filho JDS.Harrison WTA.Carvalho CEM.Goulart MOF.Júnior ENS.Pinto AV. Tetrahedron Lett. 2011, 52: 2415 -
14a
Veisi H.Ghorbani-Vaghei R. Tetrahedron 2010, 66: 7445 -
14b
Qi C.Jiang H.Huang L.Chen Z.Chen H. Synthesis 2011, 387 - 15
Kuo C.-W.More SV.Yao C.-F. Tetrahedron Lett. 2006, 47: 8523 - 16
Chang M.-Y.Lee T.-W.Lin C.-H. Tetrahedron 2011, 67: 4892 -
17a
Emoto T.Kubosaki N.Yamagiwa Y.Kamikawa TA. Tetrahedron Lett. 2000, 41: 355 -
17b
de Andrade-Neto VF.Goulart MOF.da Silva Filho JF.da Silva MJ.Pinto MCFR.Pinto AV.Zalis MG.Carvalho LH.Krettli AU. Bioorg. Med. Chem. Lett. 2004, 14: 1145 - 18
Makgatho ME.Anderson R.O’Sullivan JF.Egan TJ.Freese JA.Cornelius N.van Rensburg CEJ. Drug Dev. Res. 2000, 50: 195 - 19
Wang WY.Preville P.Morin N.Mounir S.Cai WZ.Siddiqui MA. Bioorg. Med. Chem. Lett. 2000, 10: 1151
References
CCDC 807121 (3b), 810169 (3h), 818140 (3m), and 818141 (3o) contain the supplementary crystallographic data for this paper. This data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html [or from the CCDC, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44(1223)336033; e-mail: deposit@ccdc.cam.ac.uk].