Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2008(23): 3787-3792
DOI: 10.1055/s-0028-1083230
DOI: 10.1055/s-0028-1083230
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New YorkBismuth(III)-Catalyzed Rapid Synthesis of 2,3-Disubstituted Quinoxalines in Water
Further Information
Received
26 June 2008
Publication Date:
14 November 2008 (online)
Publication History
Publication Date:
14 November 2008 (online)

Abstract
A variety of 2,3-disubstituted quinoxalines are readily prepared in high yields under extremely mild conditions by cyclocondensation of arene-1,2-diamines with 1,2-dicarbonyls using a catalytic amount of bismuth(III) triflate. The reactions of 2,3-diaminopyridine with 1,2-dicarbonyls produce pyrido[2,3-b]pyrazine derivatives under similar conditions.
Key words
bismuth(III) compounds - 1,2-dicarbonyls - vicinal-diamines - quinoxalines
- 1a
He W.Meyers MR.Hanney B.Sapada A.Blider G.Galzeinski H.Amin D.Needle S.Page K.Jayyosi Z.Perrone H. Bioorg. Med. Chem. Lett. 2003, 13: 3097 - 1b
Kim YB.Kim YH.Park JY.Kim SK. Bioorg. Med. Chem. Lett. 2004, 14: 541 - 2
Sakata G.Makino K.Kuraswa Y. Heterocycles 1988, 27: 2481 ; and references cited therein - 3a
Dell A.William DH.Morris HR.Smith GA.Feeney J.Roberts GCK. J. Am. Chem. Soc. 1975, 97: 2497 - 3b
Bailly C.Echepare S.Gago F.Waring M. Anti-Cancer Drug Des. 1999, 15: 291 - 3c
Sato S.Shiratori O.Katagiri K. J. Antibiot. 1967, 20: 270 - 4a
Katoh A.Yoshida T.Ohkanda J. Heterocycles 2000, 52: 911 - 4b
Thomas KRJ.Velusamy M.Lin JT.Chuen CH.Tao YT. Chem. Mater. 2005, 17: 1860 - 4c
Dailey S.Feast WJ.Peace RJ.Sage IC.Till S.Wood EL. J. Mater. Chem. 2001, 11: 2238 - 5a
Sessler JL.Maeda H.Mizuno T.Lynch VM.Furuta H. J. Am. Chem. Soc. 2002, 124: 13474 - 5b
Crossley MJ.Johnston LA. Chem. Commun. 2002, 1122 - 5c
Yamaguchi T.Matsumoto S.Watanabe K. Tetrahedron Lett. 1998, 39: 8311 - 6a
Brown DJ. Quinoxalines: Supplement 11, In The Chemistry Heterocyclic Compounds Vol. 61:Taylor EC.Wipf P. John Wiley & Sons; New Jersey: 2004. - 6b
Bhosale RS.Sarda SR.Andhapure SS.Jadhav WN.Bhusare SR.Pawar RP. Tetrahedron Lett. 2005, 46: 7183 - 6c
More SV.Sastry MNV.Wang Ch.Yao CF. Tetrahedron Lett. 2005, 46: 6345 - 6d
Huang T.-k.Wang R.Shi L.Lu X.-x. Catal. Commun. 2008, 9: 1143 - 7a
Raw SA.Wilfred CD.Taylor RJK. Org. Biomol. Chem. 2004, 2: 788 - 7b
Kim SY.Park KH.Chung YK. Chem. Commun. 2005, 1321 - 7c
Robinson RS.Taylor RJK. Synlett 2005, 1003 - 7d
Cho CS.Renb WX.Shim SC. Tetrahedron Lett. 2007, 48: 4665 - 8a
Singh SK.Gupta P.Duggineni S.Kundu B. Synlett 2003, 2147 - 8b
Antoniotti S.Dunach E. Tetrahedron Lett. 2002, 43: 3971 - 8c
Das B.Lu KV.Suneel K.Majhi A. Tetrahedron Lett. 2007, 48: 5371 - 9a
Barluenga J.Aznar F.Liz R.Cabal M.-P. Synthesis 1985, 313 - 9b
Raw SA.Wilfred CD.Taylor RJK. Chem. Commun. 2003, 2286 - 9c
Cohen Y.Meyer AY.Rabinovitz M. J. Am. Chem. Soc. 1986, 108: 7039 - 9d
Xekoukoulotakis NP.Hadjiantoniou M.Maroulis AJ. Tetrahedron Lett. 2000, 41: 10299 - 9e
More SV.Sastry MNV.Yao CF. Green Chem. 2006, 8: 91 - 9f
Zhao Z.Wisnoski DD.Wolkenberg SE.Leister WH.Wang Y.Lindsley CW. Tetrahedron Lett. 2004, 45: 4873 - 9g
Goswami S.Adak AK. Tetrahedron Lett. 2005, 46: 221 - 10a
Mohsenzadesh F.Aghapoor K.Darabai HR. J. Braz. Chem. Soc. 2007, 18: 297 - 10b
Cho CS.Oh SG. J. Mol. Catal. A: Chem. 2007, 276: 205 - 10c
Popp FD. J. Heterocycl. Chem. 1972, 9: 1399 - 10d
Takekuma S.-i.Katayama S.Takekuma H. Chem. Lett. 2000, 614 - 10e
Sarkis GY.Al-Badri HT. J. Heterocycl. Chem. 1980, 17: 813 - 11a
Grieco PA. Organic Synthesis in Water Blackie Academic and Professional; London: 1998. - 11b
Li CJ.Chan TH. Organic Reactions in Aqueous Media John Wiley and Sons; New York: 1997. p.159 - 12a
Imamoto T. Lanthanides in Organic Synthesis Academic Press; London: 1994. - 12b
Molander GA. Chem. Rev. 1992, 92: 29 - 13a
Kobayashi SK. Synlett 1994, 689 - 13b
Kobayashi SK. J. Synth. Org. Chem., Jpn. 1995, 53: 370 - 13c
Kobayashi S. Eur. J. Org. Chem. 1999, 15 - 14a
Leonard MN.Wieland LC.Mohan RS. Tetrahedron 2002, 58: 8373 - 14b
Gaspard-Iloughmane H.Le Roux C. Eur. J. Org. Chem. 2004, 2517 - 15
Repichet S.Zwick A.Vendier L.Le Roux C.Dubac J. Tetrahedron Lett. 2002, 43: 993 - 16a
Ollevier T.Lavie-Compin G. Tetrahedron Lett. 2004, 45: 49 - 16b
Ollevier T.Nadeau E.Guay-Bégin AA. Tetrahedron Lett. 2006, 47: 8351 - 16c
Frank W.Reiss GJ.Schneider J. Angew. Chem., Int. Ed. Engl. 1995, 34: 2416