Synthesis of Heteroarylazo-substituted Calix[4]arenes

Chuan-Ming Jin; Guo-Yuan Lu; Zhen-Sheng Wang; Xiao-Zeng You; Zhong-Hua Wang; Wei Gong; Hou-Ming Wu

doi:10.1055/s-2001-14562

PAPER

Synthesis of Heteroarylazo-substituted Calix[4]arenes

Chuan-Ming Jin^a, Guo-Yuan Lu*^a, Zhen-Sheng Wang^a, Xiao-Zeng You^a, Zhong-Hua Wang^b, Wei Gong^b, Hou-Ming Wu^b
^a Department of Chemistry, State Key Laboratory of Coordination Chemistry, Nanjing University, Nanjing 210093, P. R. China
^b State Key Laboratory of Bio-organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. China
Fax: +86(25)3317761; e-Mail: nnj.lugy@jlonline.com;

Abstract

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Abstract

This paper reports a novel method for preparing heteroarylazo- substituted calix[4]arenes, in which heteroaromatic amines were diazotized with isoamyl nitrite in EtONa-EtOH under refluxing conditions. Mono(heteroarylazo)-, bis(heteroarylazo)- and tetrakis(heteroarylazo)-substituted calix[4]arenes were obtained as main product by diazo-coupling in different molar ratio to calix[4]arenes under pH 7-9 in non-aqueous solution at 0-5 °C. Based on the method, eight novel heteroarylazo-substituted calix[4]arenes have been synthesized by diazo-coupling reaction of calix[4]arene with diazonium salt solutions of 4-aminopyridine or 2-aminothiazole.

Key words

calix[4]arene - diazo coupling - isoamyl nitrite - synthesis

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References

<A NAME="RF00701SS-1">1</A> Vicens J. Bhömer V. Calixarene-A Versatile Class of Macrocyclic Compounds Kluwer; Dordrecht: 1991.

<A NAME="RF00701SS-2">2</A> Pochini A. Ungaro R. Calix[4]arenes and Related Hosts, In Comprehensive Supramolecular Chemistry Lehn J.-M. Vögtle F. Pergamon; New York: 1996. p.103-142

<A NAME="RF00701SS-3">3</A> Ikeda A. Shinkai S. Chem. Rev. 1997, 97: 1713

<A NAME="RF00701SS-4">4</A> Shinkai S. Araki K. Shibata J. Tsugawa D. Manabe O. Chem. Lett. 1989, 931

<A NAME="RF00701SS-5">5</A> Shinkai S. Araki K. Shibata J. Tsugawa D. Manabe O. J. Chem. Soc., Perkin Trans.1 1990, 3333

<A NAME="RF00701SS-6">6</A> Nomura E. Taniguchi H. Tamura S. Chem. Lett. 1989, 1125

<A NAME="RF00701SS-7">7</A> Morita Y. Agawa T. Nomura E. Taniguchi H. J. Org. Chem. 1992, 57: 3658

<A NAME="RF00701SS-8">8</A> Tyson JC. Moore JL. Hughes KD. Collard DM. Langmuir 1997, 13: 2068

<A NAME="RF00701SS-9">9</A> Yeh M.-L. Tang F.-S. Chen S.-L. Liu W.-C. Lin L.-G. J. Org. Chem. 1994, 59: 754

<A NAME="RF00701SS-10">10</A> Takamura N. Mizoguchi T. Koga K. Yamada S. Tetrahedron 1975, 31: 227

<A NAME="RF00701SS-11">11</A> Iwamoto K. Araki K. Shinkai S. Tetrahedron 1991, 47: 4325

<A NAME="RF00701SS-12">12</A> Jaime C. deMendoza J. Prados P. Nieto PM. Sanchez C. J. Org. Chem. 1991, 56: 3372

<A NAME="RF00701SS-13">13</A> Lu GY. Li Q. Liu F. Wan XB. Chin. J. Chem. 2000, 18: 207

<A NAME="RF00701SS-14">14</A> Yang XG. McBranch D. Swanson B. Li DQ. Angew. Chem., Int. Ed. Engl. 1996, 35: 538

<A NAME="RF00701SS-15">15</A> Kelderman E. Derhaeg L. Heesink GJT. Verboom W. Engbersen JFJ. VanHulst NF. Persoons A. Reinhoudt DN. Angew. Chem., Int. Ed. Engl. 1992, 31: 1075

<A NAME="RF00701SS-16">16</A> VanLoon JD. Arduini A. Coppi L. Verboom W. Pochini A. Ungaro R. Harkema S. Reinhoudt DN. J. Org. Chem. 1990, 55: 5639