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Synthesis 2015; 47(17): 2680-2689
DOI: 10.1055/s-0034-1380678
DOI: 10.1055/s-0034-1380678
paper
A Combined Experimental and Theoretical Study of the Ammonium Bifluoride Catalyzed Regioselective Synthesis of Quinoxalines and Pyrido[2,3-b]pyrazines
Further Information
Publication History
Received: 09 February 2015
Accepted after revision: 02 April 2015
Publication Date:
19 May 2015 (online)
Abstract
Ammonium bifluoride was efficiently used at a 0.5 mol% loading to catalyze the cyclocondensation of 1,2-arylenediamines with 1,2-dicarbonyl compounds at room temperature in methanol–water to give quinoxalines or pyrido[2,3-b]pyrazines in excellent yields. Importantly, 2,8-disubstituted quinoxalines and 3-substituted pyrido[2,3-b]pyrazines were regioselectively formed by the reaction of arylglyoxals with 3-methylbenzene-1,2-diamine or pyridine-2,3-diamine, respectively. An analysis of the density functional theory reactivity indices explained the catalytic role of ammonium bifluoride.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1380678. Included are NMR spectra of the compounds 3c, 5e, 5f, 5j, 5g, 5h, 5i, 6j, 6h, and 6i.
- Supporting Information
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References
- 1 Ajani OO. Eur. J. Med. Chem. 2014; 85: 688
- 2 Sonawane ND, Rangnekar DW. J. Heterocycl. Chem. 2002; 39: 303
- 3 Thomas KR. J, Velusamy M, Lin JT, Chuen C.-H, Tao Y.-T. Chem. Mater. 2005; 17: 1860
- 4 Dailey S, Feast WJ, Peace RJ, Sage IC, Till S, Wood EL. J. Mater. Chem. 2001; 11: 2238
- 5 Brown DJ. In: The Chemistry of Heterocyclic Compounds . Vol. 61, Suppl. II. Taylor EC, Wipf P. Wiley Interscience; Hoboken: 2004
- 6a Saifina DF, Mamedov VA. Russ. Chem. Rev. 2010; 79: 351
- 6b Mamedov VA, Zhukova NA. Prog. Heterocycl. Chem. 2012; 24: 55
- 7 Nageswar YV. D, Reddy KH. V, Ramesh K, Murthy SN. Org. Prep. Proced. Int. 2013; 45: 1
- 8 Wang S, Miller W, Milton J, Vicker N, Stewart A, Charlton P, Mistry P, Hardick D, Denny WA. Bioorg. Med. Chem. Lett. 2002; 12: 415
- 9a Darabi HR, Aghapoor K, Mohsenzadeh F, Jalali MR, Talebian S, Ebadi-Nia L, Khatamifar E, Aghaee A. Bull. Korean Chem. Soc. 2011; 32: 213
- 9b Khalafy J, Marjani AP, Haghipour M. Curr. Chem. Lett. 2013; 2: 21
- 9c Aghapoor K, Mohsenzadeh F, Shakeri A, Darabi HR, Ghassemzadeh M, Neumüller B. J. Organomet. Chem. 2013; 743: 170
- 9d Lassagne F, Chevallier F, Mongin F. Synth. Commun. 2014; 44: 141
- 10a Camps F, Chamorro E, Gasol V, Guerrero A. J. Org. Chem. 1989; 54: 4294
- 10b Kim K.-Y, Kim BC, Lee HB, Shin H. J. Org. Chem. 2008; 73: 8106
- 11 Ooi T, Doda K, Maruoka K. J. Am. Chem. Soc. 2003; 125: 2054
- 12 Lu H, Zhang F.-M, Pan J.-L, Chen T, Li Y.-F. J. Org. Chem. 2014; 79: 546
- 13 Darabi HR, Tahoori F, Aghapoor K, Taala F, Mohsenzadeh F. J. Braz. Chem. Soc. 2008; 19: 1646
- 14 Cai J.-J, Zou J.-P, Pan X.-Q, Zhang W. Tetrahedron Lett. 2008; 49: 7386
- 15a Geerlings P, De Proft F, Langenaeker W. Chem. Rev. 2003; 103: 1793
- 15b Ess DH, Jones GO, Houk KN. Adv. Synth. Catal. 2006; 348: 2337
- 16 Domingo LR, Oliva M, Andrés J. J. Org. Chem. 2001; 66: 6151
- 17 Parr RG, v. Szentpály L, Liu S. J. Am. Chem. Soc. 1999; 121: 1922
- 18 Domingo LR, Aurell MJ, Pérez P, Contreras R. Tetrahedron 2002; 58: 4417
- 19 Domingo LR, Andrés J. J. Org. Chem. 2003; 68: 8662
- 20 Domingo LR, Chamorro E, Pérez P. J. Org. Chem. 2008; 73: 4615
- 21 Jaramillo P, Domingo LR, Chamorro E, Pérez P. J. Mol. Struct.: THEOCHEM 2008; 865: 68
- 22 Domingo LR, Aurell MJ, Pérez P, Contreras R. J. Phys. Chem. A 2002; 106: 6871
- 23 Pérez P, Domingo LR, Duque-Noreña M, Chamorro E. J. Mol. Struct.: THEOCHEM 2009; 895: 86
- 24 Gottlieb HE, Kotlyar V, Nudelman A. J. Org. Chem. 1997; 62: 7512
- 25 Hauze DB, Petrovskaia O, Taylor B, Joullie MM, Ramotowski R, Cantu AA. J. Forensic Sci. 1998; 43: 744
- 26 Batchu H, Batra S. Eur. J. Org. Chem. 2012; 2935
- 27 Wang P, Tao W.-J, Sun X.-L, Liao S, Tang Y. J. Am. Chem. Soc. 2013; 135: 16849
- 28 Kipnis F, Ornfelt J. J. Am. Chem. Soc. 1948; 70: 3948
- 29 Kipnis F, Ornfelt J. J. Am. Chem. Soc. 1946; 68: 2734
- 30 Sato T, Ohto M. Bull. Chem. Soc. Jpn. 1955; 28: 480
- 31 Vogel AI, Furnis BS. Vogel’s Textbook of Practical Organic Chemistry . 5th ed Longman; Harlow: 1989
- 32 Altomare A, Burla MC, Camalli M, Cascarano GL, Giacovazzo C, Guagliardi A, Moliterni AG. G, Polidori G, Spagna R. J. Appl. Crystallogr. 1999; 32: 115
- 33 Sheldrick GM. Acta Crystallogr., Sect. A 2008; 64: 112
- 34 Farrugia LJ. J. Appl. Crystallogr. 2012; 45: 849
- 35 Nandi GC, Samai S, Kumar R, Singh MS. Synth. Commun. 2011; 41: 417
- 36 Raju BC, Theja ND, Kumar JA. Synth. Commun. 2009; 39: 175
- 37 Giordano C, Belli A, Casagrande F, Guglielmetti G, Citterio A. J. Org. Chem. 1981; 46: 3149
- 38 Tan J, Tang W, Sun Y, Jiang Z, Chen F, Xu L, Fan Q, Xiao J. Tetrahedron 2011; 67: 6206
- 39 Wunderlich SH, Rohbogner CJ, Unsinn A, Knochel P. Org. Process Res. Dev. 2010; 14: 339
- 40 Wu F.-W, Hou R.-S, Wang H.-M, Kang I.-J, Chen L.-C. Heterocycles 2011; 83: 2313
- 41 Lin P.-Y, Hou R.-S, Wang H.-M, Kang I.-J, Chen L.-C. J. Chin. Chem. Soc. (Weinheim, Ger.) 2009; 56: 683
- 42 Kauffmann T, Ghanem M, Otter R. Chem. Ber. 1982; 115: 459
- 43 Nguyen TB, Retailleau P, Al-Mourabit A. Org. Lett. 2013; 15: 5238
- 44 Crystallographic data for compounds 5e, 5f, 5j, 5g, 5′g, 5h, 5i, 5′i, 6j, and 6i have been deposited with the accession numbers CCDC 887677, 1034992, 1034993, 1034994, 1034995, 901747, 887678, 887679, 1034996, and 887680, respectively, and can be obtained free of charge from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK, Fax: +44(1223)336033, E-mail: deposit@ccdc.cam.ac.uk, Web site: www.ccdc.cam.ac.uk/conts/retrieving.html.
- 45a Lee C, Yang W, Parr RG. Phys. Rev. B: Condens. Matter Mater. Phys. 1988; 37: 785
- 45b Becke AD. J. Chem. Phys. 1993; 98: 5648
- 46 Hehre WJ, Radom L, Schleyer Pv. R, Pople JA. Ab Initio Molecular Orbital Theory. Wiley; New York: 1986
- 47a Reed AE, Weinstock RB, Weinhold F. J. Chem. Phys. 1985; 83: 735
- 47b Reed AE, Curtiss LA, Weinhold F. Chem. Rev. 1988; 88: 899
- 48a Parr RG, Pearson RG. J. Am. Chem. Soc. 1983; 105: 7512
- 48b Parr RG, Yang W. Density Functional Theory of Atoms and Molecules. Oxford University Press; Oxford: 1989
- 49 Kohn W, Sham LJ. Phys. Rev. A: At., Mol., Opt. Phys. 1965; 140: 1133
- 50 Domingo LR, Pérez P, Sáez JA. RSC Adv. 2013; 3: 1486
- 51 Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Li X, Hratchian HP, Izmaylov AF, Bloino J, Zheng G, Sonnenberg JL, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery JA, Peralta JE. Jr, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar SS, Tomasi J, Cossi M, Rega N, Millam JM, Klene M, Knox JE, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Martin RL, Morokuma K, Zakrzewski VG, Voth GA, Salvador P, Dannenberg JJ, Dapprich S, Daniels AD, Farkas O, Foresman JB, Ortiz JV, Cioslowski J, Fox DJ. Gaussian 09 . Gaussian, Inc; Wallingford: 2009