Synthesis of Coumarin/Phenanthridine-Fused Heterocycles and Their Photochemical and Thermochromic Properties

被引：51

作者：

Chen, Jiun-Jia ^{[1
]}

Li, Kuan-Ting ^{[1
]}

Yang, Ding-Yah ^{[1
]}

机构：

[1] Tunghai Univ, Dept Chem, Taichung 40704, Taiwan

来源：

ORGANIC LETTERS | 2011年 / 13卷 / 07期

关键词：

COUMARINS; DNA; DERIVATIVES; DYES;

D O I：

10.1021/ol200117b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Four coumarin and phenanthridine-fused heterocycles were efficiently synthesized using base-mediated annulation of N-alkylquinolinium iodide and coumarin as a key step. One compound is found to be sensitive to light and changes color upon UV irradiation; the others are sensitive to heat and possess negative thermochromic properties. A novel light- and heat-sensitive molecular skeleton is introduced.

引用

收藏

页码：1658 / 1661

页数：4

相关论文

共 27 条

[1]

Alba FJ, 2001, ELECTROPHORESIS, V22, P399, DOI 10.1002/1522-2683(200102)22:3<399::AID-ELPS399>3.0.CO

[2]

2-D

[3]

ALDOSHIN SM, 1991, IZV AN SSR K, P1808

[4] Molecular determinants for DNA minor groove recognition: Design of a bis-guanidinium derivative of ethidium that is highly selective for AT-rich DNA sequences [J].

Bailly, C ;

Arafa, RK ;

Tanious, FA ;

Laine, W ;

Tardy, C ;

Lansiaux, A ;

Colson, P ;

Boykin, DW ;

Wilson, WD .

BIOCHEMISTRY, 2005, 44 (06) :1941-1952

[5] Coumarins derivatives as dual inhibitors of acetylcholinesterase and monoamine oxidase [J].

Brühlmann, C ;

Ooms, F ;

Carrupt, PA ;

Testa, B ;

Catto, M ;

Leonetti, F ;

Altomare, C ;

Carotti, A .

JOURNAL OF MEDICINAL CHEMISTRY, 2001, 44 (19) :3195-3198

[6] Structure, reactivity, and application of some triketone derivatives [J].

Chen, You-Sheng ;

Kuo, Pei-Yu ;

Shie, Tien-Lan ;

Yang, Ding-Yah .

TETRAHEDRON, 2006, 62 (40) :9410-9416

[7] Synthesis of coumarins, 4-hydroxycoumarins, and 4-hydroxyquinolinones by tellurium-triggered cyclizations [J].

Dittmer, DC ;

Li, Q ;

Avilov, DV .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (12) :4682-4686

[8] REACTIONS OF 5-METHYLPHENANTHRIDINIUM IODIDE WITH NUCLEOPHILES AND REACTION-PRODUCTS CONVERSION [J].

DOSTAL, J ;

POTACEK, M ;

NECHVATAL, M .

COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1993, 58 (02) :395-403

[9] Oligothiophene-containing coumarin dyes for efficient dye-sensitized solar cells [J].

Hara, K ;

Wang, ZS ;

Sato, T ;

Furube, A ;

Katoh, R ;

Sugihara, H ;

Dan-Oh, Y ;

Kasada, C ;

Shinpo, A ;

Suga, S .

JOURNAL OF PHYSICAL CHEMISTRY B, 2005, 109 (32) :15476-15482

[10] Toward safer methodologies for the synthesis of polyheterocyclic systems:: intramolecular arylation of arenes under Mizoroki-Heck reaction conditions [J].

Hernández, S ;

SanMartin, R ;

Tellitu, I ;

Domínguez, E .

ORGANIC LETTERS, 2003, 5 (07) :1095-1098