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Future Medicinal Chemistry Volume 1, 2009 - Issue 5
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Research Article

Gallium (III) Triflate-Catalyzed Synthesis of Heterocycles: Quinoxalines, 1,5-Benzodiazepines and Their Fluorinated Derivatives

G K Surya PrakashDonald P. and Katherine B. Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California, 837 Bloom Walk, Los Angeles, CA90089-91661, USACorrespondence[email protected]
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,
Habiba VaghooDonald P. and Katherine B. Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California, 837 Bloom Walk, Los Angeles, CA90089-91661, USAView further author information
,
Arthi VenkatDonald P. and Katherine B. Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California, 837 Bloom Walk, Los Angeles, CA90089-91661, USAView further author information
,
Chiradeep PanjaDonald P. and Katherine B. Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California, 837 Bloom Walk, Los Angeles, CA90089-91661, USAView further author information
,
Sujith ChackoDonald P. and Katherine B. Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California, 837 Bloom Walk, Los Angeles, CA90089-91661, USAView further author information
,
Thomas MathewDonald P. and Katherine B. Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California, 837 Bloom Walk, Los Angeles, CA90089-91661, USAView further author information
&
George A OlahDonald P. and Katherine B. Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California, 837 Bloom Walk, Los Angeles, CA90089-91661, USAView further author information
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Pages 909-920 | Published online: 19 Aug 2009

Bibliography

  • Katritzky AR , ReesCW. Comprehensive Heterocyclic Chemistry (Volume 3). Pergamon, Oxford, UK (1984).
  • Cheeseman GWH , RF Cookson. In: The Chemistry of Heterocyclic Compounds (Volume 35). Weissberge A, Taylor EC (Eds). J Wiley and Sons, NY, USA (1979).
  • Lindsley CW , ZhaoZ, LeisterWHet al. Allosteric akt (PKB) inhibitors: discovery and sar of isozyme selective inhibitors. Bioorg. Med. Chem. Lett. 15, 761–764 (2005).
  • Hui X , DesrivotJ, BoriesCet al. Synthesis and antiprotozoal activity of some new synthetic substituted quinoxalines. Bioorg. Med. Chem Lett. 16, 815–820 (2006).
  • Kim YB , KimYH, ParkJY, KimSK. Synthesis and biological activity of new quinoxaline antibiotics of echinomycin analogues.Bioorg. Med. Chem. Lett.14, 541–544 (2004).
  • He W , MeyersMR, HanneyBet al. Potent quinoxaline-based inhibitors of pdgf receptor tyrosine kinase activity. Part 2: the synthesis and biological activities of RPR127963, an orally bioavailable inhibitor. Bioorg. Med. Chem. Lett. 13, 3097–3100 (2003).
  • Gilbert DE , Van Der Marel GA, Van Boom JH, Feigon J. Unstable hoogsteen base pairs adjacent to echinomycin binding sites within a DNA duplex. Proc. Natl. Acad. Sci. USA89, 3006–3010 (1988).
  • Dietrich B , DiederichsenU. Synthesis of cyclopeptidic analogues of triostin A with quinoxalines or nucleobases as chromophores.Eur. J. Org. Chem.2005(1), 147–153 (2004).
  • Dirlam JP , PresslitzJE, WilliamsBJ. Synthesis and antibacterial activity of some 3-[(alkylthio)methyl]quinoxaline-1-oxide derivatives.J. Med. Chem.26, 1122–1126 (1983).
  • Catarzi D , ColottaV, VaranoFet al. synthesis and biological evaluation of novel 9-heteroaryl substituted 7-chloro-4,5-dihydro-4-oxo-1,2,4-triazolo[1,5-a]quinoxaline-2-carboxylates (TQX) as (R,S)-2-amino-3-(3-hydroxy-5-methylisoxazol-4-yl)propionic acid (AMPA) receptor antagonists. Chem. Pharm. Bull. 56(8), 1085–1091 (2008).
  • Jaung JY . Synthesis and halochromism of new quinoxaline fluorescent dyes.Dyes Pigments71, 245–250 (2006).
  • Sakata G , MakinoK, KarasawaY. An efficient protocol for the synthesis of quinoxaline derivatives at room temperature using molecular iodine as the catalyst.Heterocycles27, 2481–2515 (1988).
  • Nurulla I , YamaguchiI, YamamotoT. Preparation and properties of new II-conjugated polyquinoxalines with aromatic fused rings in the side chain.Polym. Bull.44, 231–238 (2000).
  • Yamamoto T , SugiyamaK, KushidaT, InoueT, KanbaraT. Preparation of new electron-accepting II-conjugated polyquinoxalines. Chemical and electrochemical reduction, electrically conducting properties, and use in light-emitting diodes.J. Am. Chem. Soc.118, 3930–3937 (1996).
  • Brown DJ . Quinoxalines: supplement II. In: The Chemistry of Heterocyclic Compounds. Taylor EC, Wipf P (Eds). John Wiley & Sons, NJ, USA (2004).
  • Bhosale RS , SardaSR, ArdhapureSS, JadhavWN, BhusareSR, PawarRP. An efficient protocol for the synthesis of quinoxaline derivatives at room temperature using molecular iodine as the catalyst.Tetrahedron Lett.46, 7183–7186 (2005).
  • Heravi MM , BakhtiariK, TehraniMH, JavadiNM, OskooieHA. Facile synthesis of quinoxaline derivatives using O-iodoxybenzoic acid (IBX) at room temperature. ArkivocXVI, 16–22 (2006).
  • Huang T , WangR, ShiL, LuX. Montmorillonite K-10. An efficient and reusable catalyst for the synthesis of quinoxaline derivatives in water.Catal. Commun.9, 1143–1147 (2008).
  • Hazarika P , GogoiP, KonwarD. Efficient and green method for the synthesis of 1,5-benzodiazepine and quinoxaline derivatives in water.Synth. Commun.37, 3447–3454 (2007).
  • More SV , SastryMNV, YaoCF. Cerium(IV) ammonium nitrate (CAN) as a catalyst in tap water: a simple, efficient and green approach to the synthesis of quinoxalines.Green Chem.8, 91–95 (2006).
  • Raw SA , WilfredCD, TaylorRJK. Tandem oxidation processes for the preparation of nitrogen-containing heteroaromatic and heterocyclic compounds.Org. Biomol. Chem.2, 788–796 (2004).
  • Venkatesh C , SinghB, MahataPK, JunjappaH. Heteroannulation of nitroketene N,S-arylaminoacetals with POCl3: a novel highly regioselective synthesis of unsymmetrical 2,3-substituted quinoxalines. Org. Lett.7, 2169–2172 (2005).
  • Takabatake T , ItoH, TakeiA, MiyazawaT, HasegawaM, MiyairiS. Synthesis of quinoxaline 1,4-dioxides from benzofuroxan proceeds not in, but on zeolite.Heterocycles60, 537–550 (2003).
  • Heravi MM , TaheriS, BakhtiariK, OskooieHA. On water. A practical and efficient synthesis of quinoxaline derivatives catalyzed by CuSO4•5H2O. Catal. Commun.8, 211–214 (2007).
  • Olah GA , FarooqO, Cheng,LX, Farnia,MAF, AklonisJJ. Cationic ring-opening polymerization of tetrahydrofuran with boron, aluminum, and gallium tristriflate.J. Appl. Polym. Sci.45, 1355 (1992).
  • Olah GA , FarooqO, FarniaSMF, OlahJA. Friedel-crafts chemistry. 11. Boron, aluminum, and gallium tris(trifluoromethanesulfonate) (triflate): effective new friedel-crafts catalysts.J. Am. Chem. Soc.110, 2560–2565 (1998).
  • Prakash GKS , YanP, TörökB, BusciI, TanakaM, OlahGA. Gallium(III) trifluormethanesulfonate: a water-tolerant, reusable lewis acid catalyst for friedel-crafts reactions.Catal. Lett.85, 1–6 (2003).
  • Prakash GKS , YanP, TorokB, OlahGA. Superacid catalyzed hydroxyalkylation of aromatics with ethyl trifluoropyruvate: a new synthetic route to Mosher’s acid analogs.Synlett4, 527–531 (2003).
  • Prakash GKS , YanP, TorokB, OlahGA. Superacidic trifluoromethanesulfonic acid-induced cycli-acyalkylation of aromatics.Catal. Lett.87, 109–112 (2003).
  • Yan P , BatamackP, PrakashGKS, OlahGA. Gallium(III) triflate-catalyzed dehydration of aldoximes.Catal. Lett.101, 141–143 (2005).
  • Yan P , BatamackP, PrakashGKS, OlahGA. Gallium (III) triflate catalyzed beckmann rearrangement.Catal. Lett.103, 165–168 (2005).
  • Deng X -M, Sun X-L, Tang Y. Highly regioselective rearrangement of 2-substituted vinylepoxides catalyzed by gallium(III) triflate. J. Org. Chem.70, 6537–6540 (2005).
  • Lacey JR , AnzalonePW, DuncanCM, HackertMJ, MohanRS. A study of epoxyolefin cyclizations catalyzed by bismuth trifluoromethanesulfonate and other metal triflates.Tetrahedron Lett.46, 8507–8511 (2005).
  • Nguyen R -V, Li C-J. An annulation toward fused bicyclolactones. J. Am. Chem. Soc.127, 17184–17185 (2005).
  • Yan P . PhD Thesis, University of Southern California, CA, USA (2004).
  • Boumizane K , Herzog-CanceMH, JonesDJ, PascalJL, PotierJ, RoziereJ. Synthesis, vibrational spectroscopy and EXAFS analysis of some divalent and trivalent trifluoromethanesulphonato complexes.Polyhedron10, 2757–2769 (1991).
  • Habiba V . PhD Thesis, University of Southern California (2008). Preliminary results. Presented at: 234th ACS National Meeting. Boston, MA, USA 19–23 August 2007.
  • Raju BC , ThejaND, KumarJA. Efficient and inexpensive synthesis of benzimidazoles and quinoxalines.Synth. Commun.39, 175–188 (2009).
  • More SV , SastryMNV, Wang C-C, Yao C-F. Molecular iodine. A powerful catalyst for the easy and efficient synthesis of quinoxalines. Tetrahedron Lett.46, 6345–6348 (2005).
  • Potewar TM , IngaleSA, SrinivasanKV. Efficient synthesis of quinoxalines in the ionic liquid 1-n-butylimidazolium tetrafluoroborate ([Hbim]BF4) at ambient temperature.Synth. Commun.38, 3601–3612 (2008).
  • Patel M , McHughRJ, CordovaBet al. Synthesis and evaluation of quinoxalinones as HIV-1 reverse transcriptase inhibitors. Bioorg. Med. Chem. Lett. 10, 1729–1731 (2000).
  • Fukushima Y , IshiiN. (Trifluoromethyl)quinoxaline compunds, their preparation, and pesticides containing them.Jpn. Kokai Tokkyo Koho38 (2004), JP 2004346016(A).
  • Prakash GKS , MathewT, PanjaC, VaghooH, VenkataramanK, OlahGA. Efficient one-pot synthesis of fluorinated benzimidazolines, benzothiazolines, benzoxazolines, and dihydrobenzoxazinones using gallium(III) triflate as a catalyst.Org. Lett.9, 179–182 (2007).
  • Prakash GKS , MathewT, PanjaC, AlconcelS, VaghooH, DoC. Gallium (III) triflate catalyzed efficient strecker reaction of ketones and their fluorinated analogs.Proc. Natl. Acad. Sci. USA104, 3703–3706 (2007).
  • Kirsch P . Modern Fluoroorganic Chemistry. Wiley-VCH, Weinheim, Germany (2004).
  • Chambers RD . Fluorine in Organic Chemistry. Blackwell, Oxford, UK (2004).
  • Cass LM , MooreKH, DallowNS, JonesAE, SissonJR, PrinceWT. The bioavailability of the novel nonnucleoside reverse transcriptase inhibitor GW420867X is unaffected by food in healthy male volunteers.J. Clin. Pharmacol.41, 528–535 (2001).
  • Grossi G , Di BraccioM, RomaGet al. 1,5-benzodiazepines: part XIII. Substituted 4H-[1,2,4]triazolo[4,3-α][1,5]benzodiazepin-5-amines and 4H-imidazo[1,2-α][1,5]benzo-diazepin-5- amines as analgesic, anti-inflammatory and/or antipyretic agents with low acute toxicity. Eur. J. Med. Chem.37, 933–944 (2002).
  • Ricaurte R , BraulioI, RodrigoA, JairoO. Preparation of some light-sensitive 2-nitrophenyl-2,3-dihydro-1H-benzodiazepines.Arkivoc.13, 67–71 (2004).
  • Saeed AAH , EbraheemEK, AbboHS. Cyclization of new β-diketone schiff bases into 1,5-benzodiazepines in acid medium.Canad. J. Spectr.30, 27–30 (1985).

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