Synthesis of tetrafunctionalized pentiptycenequinones for construction of cyclic dimers with a cylindrical shape by boronate ester formation

被引：13

作者：

Akine, Shigehisa ^{[1
]}

Kusama, Daisuke ^{[2
]}

Takatsuki, Yuri ^{[1
,2
]}

Nabeshima, Tatsuya ^{[2
]}

机构：

[1] Kanazawa Univ, Grad Sch Nat Sci & Technol, Kanazawa, Ishikawa 9201192, Japan

[2] Univ Tsukuba, Fac Pure & Appl Sci, Tsukuba, Ibaraki 3058571, Japan

来源：

TETRAHEDRON LETTERS | 2015年 / 56卷 / 34期

关键词：

Iptycene; Boronate; Macrocycle; Belt-like structure; Quinone; TRIPTYCENE; COMPLEXATION; IPTYCENES; QUINONES; BINDING; BELTS;

D O I：

10.1016/j.tetlet.2015.06.070

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

New tetrasubstituted pentiptycenequinone derivatives 1 and 2 having two sets of dial moieties in a syn orientation were synthesized from the corresponding 2,3-disubstituted anthracene derivatives. The semicircular scaffold of these molecules is expected to be useful to create a belt-like structure having an aromatic Indeed, the reaction of 1 with 1,4-phenylenediboronic acid or 4,4'-biphenyldiboronic acid quantitatively gave a 2:2 macrocyclic product via boronate ester formation. The efficient formation of these cyclic structures can be explained by favorable intramolecular cyclization at the final step. (C) 2015 Elsevier Ltd. All rights reserved.

引用

页码：4880 / 4884

页数：5

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