Abstract.
A variety of biologically important quinoxaline derivatives has been efficiently synthesized in excellent yields under extremely mild conditions using PEG-600 and water. This inexpensive, non-toxic, eco-friendly and readily available system efficiently condensed several aromatic as well as aliphatic 1,2-diketones with aromatic and aliphatic 1,2-diamines to afford the products in excellent yield. Polyethylene glycol (PEG) can be recovered and recycled.
Article PDF
Avoid common mistakes on your manuscript.
References
(a) He W, Meyers M R, Hanney B, Sapada A, Blider G, Galzeinski H, Amin D, Needle S, Page K, Jayyosi Z and Perrone H 2004 Bioorg. Med. Chem. Lett. 13 3097; (b) Kim Y B, Kim Y H, Park J Y and Kim S K 2004 Bioorg. Med. Chem. Lett. 14 541; (c) Gazit A, App H, McMohan G, Chen J, Levitzki A and Bohmer F 1996 J. Med. Chem. 39 2170
(a) Jaso A, Zarranz B, Aldana I and Monge A 2005 J. Med. Chem. 48 2019; (b) Seitz L E, Suling W J and Reynolds R C 2002 J. Med. Chem. 45 5604; (c) Sakata G, Makino K, and Kuraswa Y 1988 Heterocycles 27 2481
Jonathan L S, Hiromitsu M, Toshihisa M, Vincent M L and Hiroyuki F J 2002 Chem. Commun. 8 862
(a) Jonathan L S, Hiromitsu M, Toshihisa M, Vincent M L and Hiroyuki F 2002 J. Am. Chem. Soc. 124 13474; (b) Peter P C, Gang Z, Grace A M, Carlos H and Linda M G T 2004 Org. Lett. 6 33
Sascha O and Rudiger F 2004 Synlett. 9 1509
(a) Dailey S, Feast J W, Peace R J, Saga R C, Till S and Wood E L 2001 J. Mater. Chem. 11 2238; (b) O’Brien D, Weaver M S, Lidzey D G and Bradley D C 1996 Appl. Phys. Lett. 69 881
Brock E D, Lewis D M, Yousaf T I and Harper H H 1999 (The Procter and Gamble Company, USA) WO 9951688
Dickeson J E and Summers L A 1970 Aust. J. Chem. 23 1023
Amouyal E, Homsi A, Chambron J-C and Sauvage J-P 1990 Dalton Trans. 6 1841
Bolger J, Gourdon A, Ishow E and Launay J-P 1995 Chem. Commun. 17 1799
(a) Gupta N, Grover N, Neyhart G A, Liang W, Singh P and Thorp H H 1992 Angew. Chem. 31 1048; (b) Chetna P R, Rao R, Roy M and Patra A K 2009 Inorg. Chem. Acta 362 4692; (c) Miranda F S, Signori A M, Vicente J, Souza B, Priebe J P, Szpoganicz B, Goncalves N S and Neves A 2008 Tetrahedron 64 5410
(a) Zhang L and Li B J 2009 Lumin. 129 1304; (b) Bolger J, Gourdon A, Ishow E and Launay J-P 1996 Inorg. Chem. 35 2937; (c) Thomas K R, Marappan V, Jiann T L, Chang-Hao C and Yu-ai T 2005 Chem. Mater. 17 1860
(a) VOGEL’s Textbook of practical organic chemistry, 5th ed.; 1989, p. 1190; (b) Brown D J 2004 In the chemistry of heterocyclic compounds, quinoxalines supplements II (eds) E C Taylor and P Wipf (New Jersey; John Wiley and sons); (c) Yadav J S, Subba Reddy B V, Premalatha K and Shankar K 2008 Synthesis 23 3787; (d) Bhosale R S, Sarda S R, Jadhav W N, Bhusare S R, Ardhapure S S and Pawar R P 2005 Tetrahedron Lett. 46 7183; (e) More S V, Sastry M N V, Wang C and Yao C F 2005 Tetrahedron Lett. 46 6345
(a) Zemin W and Nicholas J E 2001 Tetrahedron Lett. 42 8115; (b) Orazio A A, Lucia D C, Paolino F, Fabio M and Stefania S 2003 Synlett. 8 1183; (c) Sanjay K S, Priya G, Srinivas D and Bijoy K 2003 Synlett. 14 2147; (d) More S V, Sastry M N V and Yao C F 2006 Green Chem. 8 91
(a) Raw S A, Wilfred C D and Taylor R J K 2003 Chem. Commun. 18 2286; (b) Kim S Y, Park K H and Chung Y K 2005 Chem. Commun. 10 1321
(a) Das B, Venkateswarlu K, Suneel K and Majhi A 2007 Tetrahedron Lett. 48 5371; (b) Madhav B, Murthy S N, Reddy V P, Rao K R and Nageshwar Y V D 2009 Tetrahedron Lett. 50 6025
Cho C S, Ren W X and Shim S C 2007 Tetrahedron Lett. 48 4665
Antoniotti S and Dunach E 2002 Tetrahedron Lett. 43 3971
Anil Kumar M, Stephen Babu M F, Srinivasulu K, Kiran Y B and Suresh Reddy C 2007 J Mol. Catal. A Chem. 265 268
(a) Bandgar B P, Bettigeri S V and Phopse J 2004 Org. Lett. 6 2105; (b) Bandgar B P, Bandgar S B, Korbad B L and Sawant S S 2007 Tetrahedron Lett. 48 1287; (c) Bandgar B P, Korbad B L, Patil S A, Bandgar S B, Chavan H V and Hote B S 2008 Aust. J. Chem. 61 700; (d) Bandgar B P, Patil S A, Korbad B L, Bandgar S B and Hote B S 2008 Aust. J. Chem. 61 552; (e) Bandgar B P, More P E, Kamble V T and Totre J V 2007 Arkivoc 48 1287; (f) Bandgar B P, Patil A V and Kamble V T 2007 Arkivoc 16 252
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
CHAVAN, H.V., ADSUL, L.K. & BANDGAR, B.P. Polyethylene glycol in water: A simple, efficient and green protocol for the synthesis of quinoxalines. J Chem Sci 123, 477–483 (2011). https://doi.org/10.1007/s12039-011-0081-8
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s12039-011-0081-8