Expeditious Synthesis of Papilionaceous
Molecules Containing Oligobenzofurans

Wen-Yu Chai; Er-Qun Yang; Yu-Long Zhang; An-Le Xie; Xiao-Ping Cao

doi:10.1055/s-0031-1290066

PAPER

Expeditious Synthesis of Papilionaceous Molecules Containing Oligobenzofurans

Wen-Yu Chai, Er-Qun Yang, Yu-Long Zhang, An-Le Xie, Xiao-Ping Cao*
State Key Laboratory of Applied Organic Chemistry and College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, 730000, P. R. of China
Fax: +86(931)8912582; e-Mail: caoxp@lzu.edu.cn;

Abstract

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Abstract

An efficient synthetic route to construct particular papilionaceous molecules containing oligobenzofurans is described. The key steps involved composing the backbone of the molecules by the Sonogashira cross-coupling reaction, followed by closing the benzofuran ring under alkaline conditions, and further aromatic cyclization of a multi-benzofuranyl precursor using ferric chloride as the oxidative reagent. Basic optical studies (UV-Vis, fluorescence, and fluorescence quantum yield) have been carried out on the synthesized molecules.

Key words

expeditious synthesis - papilionaceous molecule - oligobenzofurans - ferric chloride - oxidative aromatic cyclization

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References

<A NAME="RH85011SS-1A">1a</A> Zeni G. Larock RC. Chem. Rev. 2004, 104: 2285

<A NAME="RH85011SS-1B">1b</A> Keay BA. Comprehensive Heterocyclic Chemistry II Vol. 2: Katritzky AR. Rees CW. Scriven EFV. Pergamon; Oxford: 1996. p.395

<A NAME="RH85011SS-1C">1c</A> Cagniant P. Cagniant D. In Advances in Heterocyclic Chemistry Vol. 18: Katritzky AR. Boulton AJ. Academic Press; New York: 1975. p.337

<A NAME="RH85011SS-1D">1d</A> Nicolaou KC. Pfefferkorn JA. Roecker AJ. Cao GQ. Barluenga S. Mitchell HJ.
J. Am. Chem. Soc. 2000, 122: 9939

<A NAME="RH85011SS-2A">2a</A> Bird CW. In Progress in Heterocyclic Chemistry Vol. 5: Suschitzky H. Scriven EFV. Pergamon; Oxford: 1993. p.129

<A NAME="RH85011SS-2B">2b</A> Ono M. Kawashima H. Nonaka A. Kawai T. Haratake M. Mori H. Kung MP. Kung HF. Saji H. Nakayama M. J. Med. Chem. 2006, 49: 2725

<A NAME="RH85011SS-2C">2c</A> Chambers JJ. Kurrasch-Orbaugh DM. Parker MA. Nichols DE. J. Med. Chem. 2001, 44: 1003

<A NAME="RH85011SS-3">3</A> Saadeh H. Goodson T. Yu L. Macromolecules 1997, 30: 4608

<A NAME="RH85011SS-4A">4a</A> Hou XL. Cheung HY. Hon TY. Kwan PL. Lo TH. Tong SY. Wong HNC. Tetrahedron 1998, 54: 1955

<A NAME="RH85011SS-4B">4b</A> Duan X.-H. Liu X.-Y. Guo L.-N. Liao M.-C. Liu W.-M. Liang Y.-M. J. Org. Chem. 2005, 70: 6980

<A NAME="RH85011SS-4C">4c</A> Yao T. Zhang X. Larock RC. J. Am. Chem. Soc. 2004, 126: 11164

<A NAME="RH85011SS-5A">5a</A> Zhang H. Ferreira EM. Stoltz BM. Angew. Chem. Int. Ed. 2004, 43: 6144

<A NAME="RH85011SS-5B">5b</A> Hosokawa T. Maeda K. Koga K. Moritani I. Tetrahedron Lett. 1973, 14: 739

<A NAME="RH85011SS-5C">5c</A> Hosokawa T. Ohkata H. Moritani I. Bull. Chem. Soc. Jpn. 1975, 48: 1533

<A NAME="RH85011SS-5D">5d</A> Hosokawa T. Murahashi S.-I. Acc. Chem. Res. 1990, 23: 49

<A NAME="RH85011SS-6">6</A> Castro AMM. Chem. Rev. 2004, 104: 2939

<A NAME="RH85011SS-7A">7a</A> Arcadi A. Cacchi S. Rosario MD. Fabrizi G. Marinelli F. J. Org. Chem. 1996, 61: 9280

<A NAME="RH85011SS-7B">7b</A> Katritzky AR. Fali CN. Li J. J. Org. Chem. 1997, 62: 8205

<A NAME="RH85011SS-7C">7c</A> Larock RC. Yum EK. Doty MJ. Sham KKC. J. Org. Chem. 1995, 60: 3270

<A NAME="RH85011SS-7D">7d</A> Bishop BC. Cottrell IF. Hands D. Synthesis 1997, 1315

<A NAME="RH85011SS-7E">7e</A> Inoue M. Carson MW. Frontier AJ. Danishefsky SJ. J. Am. Chem. Soc. 2001, 123: 1878

<A NAME="RH85011SS-8A">8a</A> Hughes CC. Trauner D. Angew. Chem. Int. Ed. 2002, 41: 1569

<A NAME="RH85011SS-8B">8b</A> Wang Q. Huang Q. Chen B. Lu J. Wang H. She X. Pan X. Angew. Chem. Int. Ed. 2006, 45: 3651

<A NAME="RH85011SS-9">9</A> Iskra J. Stavber S. Zupan M. Synthesis 2004, 1869

<A NAME="RH85011SS-10">10</A> Mattern DL. J. Org. Chem. 1984, 49: 3051

<A NAME="RH85011SS-11">11</A> Zhai L. Shukla R. Rathore R. Org. Lett. 2009, 11: 3474

<A NAME="RH85011SS-12A">12a</A> Iyoda M. Adv. Synth. Catal. 2009, 351: 984

<A NAME="RH85011SS-12B">12b</A> Ohmae T. Nishinaga T. Wu M. Iyoda M. J. Am. Chem. Soc. 2010, 132: 1066

<A NAME="RH85011SS-12C">12c</A> Miyake Y. Wu M. Rahman MJ. Kuwatani Y. Iyoda M. J. Org. Chem. 2006, 71: 6110

<A NAME="RH85011SS-13A">13a</A> Rempala P. Kroulík J. King BT. J. Org. Chem. 2006, 71: 5067

<A NAME="RH85011SS-13B">13b</A> Wu J. Pisula W. Müllen K. Chem. Rev. 2007, 107: 718

<A NAME="RH85011SS-13C">13c</A> King PT. Kroulík J. Robertson CR. Rempala P. Hilton CL. Korinek JD. Gortari LM. J. Org. Chem. 2007, 72: 2279

<A NAME="RH85011SS-13D">13d</A> Zhou Y. Liu W.-J. Zhang W. Cao X.-Y. Zhou Q.-F. Ma Y. Pei J. J. Org. Chem. 2006, 71: 6822

<A NAME="RH85011SS-14">14</A> Wang T. Li Z.-Y. Xie A.-L. Yao X.-J. Cao X.-P. Kuck D. J. Org. Chem. 2011, 76: 3231

<A NAME="RH85011SS-15">15</A> Feng X. Wu J. Enkelmann V. Müllen K. Org. Lett. 2006, 8: 1145

<A NAME="RH85011SS-16">16</A> Shi Z.-F. Wang L.-J. Wang H. Cao X.-P. Zhang H.-L. Org. Lett. 2007, 9: 595

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