Unexpected intramolecular cyclization of 4-(2-halophenyl)-1H-pyrazolo[3,4-b]quinolines: formation of 5-and 7-membered rings from one starter

被引：20

作者：

Danel, Krzysztof S. ^{[1
]}

Wisla, Anna ^{[1
]}

Uchacz, Tomasz ^{[2
]}

机构：

[1] Univ Agr, Dept Chem, Balicka St 122, PL-30149 Krakow, Poland

[2] Jagiellonian Univ, Fac Chem, PL-30060 Krakow, Poland

来源：

ARKIVOC | 2009年

基金：

美国国家卫生研究院;

关键词：

Azafluoranthene; annulation; cyclodehydrohalogenation; 1H-pyrazolo[3,4-b]quinoline; ELECTROLUMINESCENCE; DERIVATIVES; RUBICENE; PYRAZOLOQUINOLINE;

D O I：

10.3998/ark.5550190.0010.a08

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Cyclization of 4-(2-halophenyl)-1H-pyrazolo[3,4-b] quinolines 3a-b and 9a-9b provided two regioisomeric compounds: 6-phenyl-6H-5,6,7-triazadibenzo[f,h] naphtho[3,2,1-cd] azulenes 4,10 and 1,3-diphenyl-3H-indeno[1,2,3-de]pyrazolo[ 3,4-b] quinolines 2,11. All of them are considered as new building blocks for optoelectronic materials. The two-step synthesis utilized readily available starting materials.

引用

页码：71 / 78

页数：8

共 37 条

[1]

AFONSO A, 1996, Patent No. 5506236

[2] Cycloaddition of o-benzyne to benzene and the inner phase of a hemicarcerand [J].

Beno, BR ;

Sheu, CM ;

Houk, KN ;

Warmuth, R ;

Cram, DJ .

CHEMICAL COMMUNICATIONS, 1998, (03) :301-302

[3] Fullerene-like chemistry at the interior carbon atoms of an alkene-centered C26H12 geodesic polyarene [J].

Bronstein, Hindy E. ;

Scott, Lawrence T. .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (01) :88-93

[4]

Chaczatrian K., 2001, ARKIVOC, V6, P63, DOI [10.3998/ark.5550190.0002.605, DOI 10.3998/ARK.5550190.0002.605]

[5]

CHEN JP, 2004, Patent No. 20040101711

[6] Facile synthesis and X-ray structure of alkoxy-functionalized dibenzo[fg,op]naphthacenes [J].

Cheng, XH ;

Höger, S ;

Fenske, D .

ORGANIC LETTERS, 2003, 5 (15) :2587-2589

[7] 2-3-BENZORUBICENE, RUBICENE, AND THEIR DERIVATIVES [J].

CLAR, E ;

WILLICKS, W .

JOURNAL OF THE CHEMICAL SOCIETY, 1958, (MAR) :942-946

[8] AROMATIC HYDROCARBONS .66. DIPERINAPHTHYLENE-ANTHRACENES [J].

CLAR, E ;

KELLY, W ;

WRIGHT, JW .

JOURNAL OF THE CHEMICAL SOCIETY, 1954, (MAR) :1108-1111

[9] INTERFERON INDUCING ACTIVITIES OF DERIVATIVES OF 1,3-DIMETHYL-4-(3-DIMETHYLAMINOPROPYLAMINO)-1H-PYRAZOLO[3,4-B]QUINOLINE AND RELATED COMPOUNDS [J].

CRENSHAW, RR ;

LUKE, GM ;

SIMINOFF, P .

JOURNAL OF MEDICINAL CHEMISTRY, 1976, 19 (02) :262-275

[10]

CRESPI VH, 2004, Patent No. 6835952

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