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
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
收藏
页码:71 / 78
页数:8
相关论文
共 50 条
  • [31] Discovery of N-[4-(1H-Pyrazolo[3,4-b]pyrazin-6-yl)-phenyl]sulfonamides as Highly Active and Selective SGK1 Inhibitors
    Halland, Nis
    Schmidt, Friedemann
    Weiss, Tilo
    Saas, Joachim
    Li, Ziyu
    Czech, Joerg
    Dreyer, Matthias
    Hofmeister, Armin
    Mertsch, Katharina
    Dietz, Uwe
    Struebing, Carsten
    Nazare, Marc
    ACS MEDICINAL CHEMISTRY LETTERS, 2015, 6 (01): : 73 - 78
  • [32] 4-(4-Methoxyphenyl)-3-methyl-1-phenyl-1,7-dihydro-5H-furo[3,4-b] pyrazolo[4,3-e]pyridin-5-one
    Wang, Qian
    Tu, Shu-Jiang
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2007, 63 : O1672 - O1673
  • [33] 3-methyl-1,4-diphenyl-1H,5H,7H-furo[3,4-b]pyrazolo[4,3-e]pyridin-5-one
    Chen, Dong-Qin
    Tu, Shu-Jiang
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2007, 63 : O1777 - O1778
  • [34] A Novel and Practical Synthesis of 5-Fluoro-1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridine-3-carbonitrile, a Key Intermediate of Vericiguat
    Bi, Siju
    Diao, Wenshuang
    Tian, Ting
    Zhou, Ting
    Lin, Kuaile
    Zhou, Weicheng
    ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2023, 27 (04) : 755 - 762
  • [35] UNEXPECTED FORMATION AND CRYSTAL-STRUCTURE OF A SPIRO[INDENE-1,7'(6'H)-PYRROLO[3,4-B] PYRIDIN]-5'-ONE
    BAHAJAJ, AA
    HITCHINGS, GJ
    MOORE, MH
    VERNON, JM
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (09): : 1211 - 1214
  • [36] SYNTHESES OF SUBSTITUTED PYRAZOLO[3,4-B]QUINOLINES, 3,4-DIHYDRO-4-OXOPYRIMIDO[4',5'-4,5]THEINO[2,3-B]QUINOLINE AND PYRIDO[1',2'-1,2]PYRIMIDO[4,5-B]QUINOLINE
    NEELIMA
    BHAT, B
    BHADURI, AP
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1986, 23 (03) : 925 - 928
  • [37] Quinoxalines.: Part 12:: Synthesis and structural study of 1-(thiazol-2-yl)-1H-pyrazolo[3,4-b]quinoxalines -: the dehydrogenative cyclization with hydroxylamine hydrochloride
    Sarodnick, G
    Heydenreich, M
    Linker, T
    Kleinpeter, E
    TETRAHEDRON, 2003, 59 (33) : 6311 - 6321
  • [38] Identification of amides derived from 1H-pyrazolo [3,4-b]pyridine-5-carboxylic acid as potent inhibitors of human nicotinamide phosphoribosyltransferase (NAMPT)
    Zheng, Xiaozhang
    Bair, Kenneth W.
    Bauer, Paul
    Baumeister, Timm
    Bowman, Krista K.
    Buckmelter, Alexandre J.
    Caligiuri, Maureen
    Clodfelter, Karl H.
    Feng, Yezhen
    Han, Bingsong
    Ho, Yen-Ching
    Kley, Nikolai
    Li, Hong
    Liang, Xiaorong
    Liederer, Bianca M.
    Lin, Jian
    Ly, Justin
    O'Brien, Thomas
    Oeh, Jason
    Oh, Angela
    Reynolds, Dominic J.
    Sampath, Deepak
    Sharma, Geeta
    Skelton, Nicholas
    Smith, Chase C.
    Tremayne, Jarrod
    Wang, Leslie
    Wang, Weiru
    Wang, Zhongguo
    Wu, Hongxing
    Wu, Jiansheng
    Xiao, Yang
    Yang, Guangxing
    Yuen, Po-Wai
    Zak, Mark
    Dragovich, Peter S.
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2013, 23 (20) : 5488 - 5497
  • [39] A monoclinic polymorph of 3,7,7-trimethyl-1-phenyl-5,6,7,8-tetrahydro-1H-pyrazolo [3,4-b]quinolin-5-one
    Mera, J
    Quiroga, J
    Cobo, J
    Low, JN
    Glidewell, C
    ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY, 2005, 61 : O442 - O444
  • [40] Palladium mediated regioselective intramolecular Heck reaction: synthesis of 1,3,4-trisubstituted pyrazolo[3,4-b]pyridines, 3H-pyrazolo[3,4-c]-isoquinolines and 3H-pyrazolo[4,3-f][1,7]-naphthyridines
    Prakash, Rashmi
    Shekarrao, Kommuri
    Saikia, Pallabi
    Gogoi, Sanjib
    Boruah, Romesh C.
    RSC ADVANCES, 2015, 5 (27): : 21099 - 21102