Synthesis of Novel 1,4-Benzoquinone-Containing
1,2,3-Triazoles: An Entry Into a New Library

Fatih Algi; Metin Balci

doi:10.1055/s-0028-1088017

PAPER

Synthesis of Novel 1,4-Benzoquinone-Containing 1,2,3-Triazoles: An Entry Into a New Library

Fatih Algi*^a,b, Metin Balci*^a
^a Department of Chemistry, Middle East Technical University, 06531 Ankara, Turkey
Fax: +90(312)2101280; e-Mail: mbalci@metu.edu.tr;
^b Laboratory of Organic Materials (LOM), Çanakkale Onsekiz Mart University, 17100 Çanakkale, Turkey
e-Mail: falgi@comu.edu.tr;

Abstract

All articles of this category

Abstract

A heretofore unexplored library of 1,4-benzoquinone-containing 1,2,3-triazoles was prepared by the application of a highly regioselective copper(I)-catalyzed process. Furthermore, the utilization of this novel triazole-1,4-benzoquinone system as an interesting class of extended, branched molecules for the construction of new supramolecular architectures is presented.

Key words

benzoquinones - azides - triazoles - copper(I) catalysis - regioselectivity

Full Text

References

<A NAME="RP13108SS-1A">1a</A> Dehne H. In Houben-Weyl Vol. E8d: Schumann E. Thieme; Stuttgart: 1994. p.305-405

<A NAME="RP13108SS-1B">1b</A> Wamhoff H. In Comprehensive Heterocyclic Chemistry Vol. 5: Katritzky AR. Rees CW. Pergamon; Oxford: 1984. p.669-732

For triazole activity studies, see:

<A NAME="RP13108SS-2A">2a</A> Alvarez R. Velazquez S. San F. Aquaro S. De C. Perno CF. Karlesson A. Balzarini J. Camarasa MJ. J. Med. Chem. 1994, 37: 4185

<A NAME="RP13108SS-2B">2b</A> Genin MJ. Allwine DA. Anderson DJ. Barbachyne MR. Emmert DE. Garmon SA. Graber DR. Grega KC. Hester JB. Hutchinson DK. Morris J. Reischer RJ. Ford CW. Zurence GE. Hamel JC. Schaadt RD. Stapertand D. Yagi BH. J. Med. Chem. 2000, 43: 953

<A NAME="RP13108SS-2C">2c</A> Brockunier LL. Parmee ER. Ok HO. Candelore MR. Casciere MA. Colwell LF. Deng L. Feeney WP. Forest MJ. Hom GJ. MacIntyre DE. Tota L. Wyvratt MJ. Fisher MH. Weber AE. Bioorg. Med. Chem. Lett. 2000, 10: 2111

<A NAME="RP13108SS-3A">3a</A> For recent reviews on organic azides, see: Brase S. Gil C. Knepper K. Zimmermann V. Angew. Chem. Int. Ed. 2005, 44: 5188

<A NAME="RP13108SS-3B">3b</A> Sha C. Mohanakrishnan AK. In The Chemistry of Heterocyclic Compounds Vol. 59: Padwa A. Pearson WH. John Wiley & Sons; Hoboken: 2002. p.623-679

For the synthesis and/or applications of 1,5-triazoles, see:

<A NAME="RP13108SS-4A">4a</A> Krasinski A. Fokin VV. Sharpless KB. Org. Lett. 2004, 6: 1237

<A NAME="RP13108SS-4B">4b</A> Zhang L. Chen X. Xue P. Sun HHY. Williams ID. Sharpless KB. Fokin VV. Jia G. J. Am. Chem. Soc. 2005, 127: 15998

<A NAME="RP13108SS-4C">4c</A> Liu D. Gao W. Dai Q. Zhang X. Org. Lett. 2005, 7: 4907

<A NAME="RP13108SS-5A">5a</A> Garanti L. Molteni G. Tetrahedron Lett. 2003, 44: 1133

<A NAME="RP13108SS-5B">5b</A> Katritzky AR. Singh SK. J. Org. Chem. 2002, 67: 9077

<A NAME="RP13108SS-5C">5c</A> Suzuki H. Nakaya C. Matano Y. Tetrahedron Lett. 1993, 34: 1055

On copper-catalyzed synthesis and/or applications of 1,2,3-triazoles, see:

<A NAME="RP13108SS-6A">6a</A> Rostovtsev VV. Green LG. Fokin VV. Sharpless KB. Angew. Chem. Int. Ed. 2002, 41: 2596

<A NAME="RP13108SS-6B">6b</A> Tornoe CW. Christensen C. Medal M. J. Org. Chem. 2002, 67: 3057

<A NAME="RP13108SS-6C">6c</A> Jin T. Kamijo S. Yamamoto Y. Eur. J. Org. Chem. 2004, 3789

<A NAME="RP13108SS-6D">6d</A> Fazio F. Bryan MC. Blixt O. Paulson JC. Wong CH. J. Am. Chem. Soc. 2002, 124: 14397

<A NAME="RP13108SS-6E">6e</A> Wang Q. Chan RC. Hilgraf R. Fokin VV. Sharpless KB. Finn MG. J. Am. Chem. Soc. 2003, 125: 3192

<A NAME="RP13108SS-6F">6f</A> Löber S. Rodriguez-Loaiza P. Gmeiner P. Org. Lett. 2003, 5: 1753

<A NAME="RP13108SS-6G">6g</A> Perez-Balderas F. Ortega-Munoz M. Morales-Sanfrutos J. Hernandez-Mateo F. Calvo-Flores FG. Calvo-Asin JA. Isac-Garcia J. Santoyo-Gonzales F. Org. Lett. 2003, 5: 1951

<A NAME="RP13108SS-6H">6h</A> Rodinov VO. Fokin VV. Finn MG. Angew. Chem. Int. Ed. 2005, 44: 2210

<A NAME="RP13108SS-7">7</A> Balci M. Çelik M. Gültekin MS. In Science of Synthesis Vol. 28: Griesbeck AG. Thieme; Stuttgart: 2006. p.31-180

<A NAME="RP13108SS-8">8</A> O’Malley PJ. Chem. Phys. Lett. 1997, 274: 251

<A NAME="RP13108SS-9">9</A> Blanchard JS. Marcinkeviciene JA. Biochemistry 1995, 34: 6621 ; and references cited therein

For structure-activity studies of 1,4-benzoquinones, see:

<A NAME="RP13108SS-10A">10a</A> Sami SM. Iyengar BS. Tarnow SE. Remers WA. Bradner WT. Schurig JE. J. Med. Chem. 1984, 27: 701

<A NAME="RP13108SS-10B">10b</A> Shaikh IA. Johnson F. Grollman AP. J. Med. Chem. 1986, 29: 1329

<A NAME="RP13108SS-10C">10c</A> Kunz KR. Iyengar BS. Dorr RT. Alberts DS. Remers WA. J. Med. Chem. 1991, 34: 2281

<A NAME="RP13108SS-10D">10d</A> Arai H. Ashizawa T. Gomi K. Kono M. Saito H. Kasai M. J. Med. Chem. 1995, 38: 3025

<A NAME="RP13108SS-10E">10e</A> Hernick M. Flader C. Borch RF. J. Med. Chem. 2002, 45: 3540

<A NAME="RP13108SS-11A">11a</A> Martinez-Manez R. Sancenon F. Chem. Rev. 2003, 103: 4419

<A NAME="RP13108SS-11B">11b</A> Callan JF. de Silva AP. Magri DC. Tetrahedron 2005, 61: 8551

<A NAME="RP13108SS-12">12</A> Algi F. Balci M. Synth. Commun. 2006, 36: 2293

<A NAME="RP13108SS-13">13</A> Halper SR. Cohen SM. Chem. Eur. J. 2003, 9: 4661 ; and references cited therein

<A NAME="RP13108SS-14">14</A> Clark CO. Poole CP. Farach HA. J. Phys. C: Solid State Phys. 1978, 11: 769