Novel synthesis of oxa[9]helicenes by Lawesson's reagent-mediated cyclization of helical quinone derivatives

被引：29

作者：

Salim, Mohammad ^{[1
,2
]}

Akutsu, Akira ^{[1
]}

Kimura, Takao ^{[1
]}

Minabe, Masahiro ^{[1
]}

Karikomi, Michinori ^{[1
]}

机构：

[1] Utsunomiya Univ, Dept Mat & Environm Chem, Grad Sch Engn, Utsunomiya, Tochigi 3218585, Japan

[2] Shahjalal Univ Sci & Technol, Dept Chem, Sch Phys Sci, Sylhet 3114, Bangladesh

来源：

TETRAHEDRON LETTERS | 2011年 / 52卷 / 35期

关键词：

Helicene; Quinone; Lawesson's reagent; Oxahelicene; THIAHELICENES; HELICENES;

D O I：

10.1016/j.tetlet.2011.06.033

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

New oxa[9]helicenes which possess one furan ring have been readily prepared by reactive helical quinone with Lawesson's reagent or phosphorus pentasulfide in good yields. The versatility of this protocol has been demonstrated with various substituted helical quinones. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：4518 / 4520

页数：3

共 25 条

[1] Chiral recognition in noncovalent bonding interactions between helicenes: right-handed helix favors right-handed helix over left-handed helix [J].

Amemiya, Ryo ;

Yamaguchi, Masahiko .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2008, 6 (01) :26-35

[2] A concise synthesis of functionalized 7-oxa-[5]-helicenes [J].

Areephong, J ;

Ruangsupapichart, N ;

Thongpanchang, T .

TETRAHEDRON LETTERS, 2004, 45 (15) :3067-3070

[3]

Ashitaka H., 1993, Nonlinear Optics, Principles, Materials, Phenomena and Devices, V4, P281

[4] Electrochemical activity of thiahelicenes: Structure effects and electrooligomerization ability [J].

Bossi, Alberto ;

Falciola, Luigi ;

Graiff, Claudia ;

Maiorana, Stefano ;

Rigamonti, Clara ;

Tiripicchio, Antonio ;

Licandro, Emanuela ;

Mussini, Patrizia Romana .

ELECTROCHIMICA ACTA, 2009, 54 (22) :5083-5097

[5] C2-symmetric dibenzosuberane-based helicenes as potential chirochromic optical switches [J].

Chen, CT ;

Chou, YC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (32) :7662-7672

[6]

CPLLINS SK, 2006, ORG BIOMOL CHEM, V4, P2518

[7] Application of the Russig-Laatsch reaction to synthesize a bis[5]helicene chiral pocket for asymmetric catalysis [J].

Dreher, SD ;

Katz, TJ ;

Lam, KC ;

Rheingold, AL .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (03) :815-822

[8] Novel synthesis of a unique helical quinone derivative by coupling reaction of 2-hydroxybenzo[c]phenanthrene [J].

Karikomi, M ;

Yamada, M ;

Ogawa, Y ;

Houjou, H ;

Seki, K ;

Hiratani, K ;

Haga, K ;

Uyehara, T .

TETRAHEDRON LETTERS, 2005, 46 (35) :5867-5869

[9] Enantioselective synthesis induced by tetrathia-[7]-helicenes in conjunction with asymmetric autocatalysis [J].

Kawasaki, Tsuneomi ;

Suzuki, Kenta ;

Licandro, Emanuela ;

Bossi, Alberto ;

Maiorana, Stefano ;

Soai, Kenso .

TETRAHEDRON-ASYMMETRY, 2006, 17 (14) :2050-2053

[10] Synthesis, crystal structure and properties of thiaheterohelicenes containing phenolic hydroxy functions [J].

Kitahara, Y ;

Tanaka, K .

CHEMICAL COMMUNICATIONS, 2002, (09) :932-933

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