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
  • [41] Development of a Scalable Synthesis for the Potent Kinase Inhibitor BMS-986236; 1-(5-(4-(3-Hydroxy-3-methylbutyl)-1H-1,2,3-triazol-1-yl)-4-(isopropylamino)pyridin-2-yl)-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile
    Arunachalam, Pirama Nayagam
    Kuppusamy, Prakasam
    Ganesan, Sivakumar
    Krishnamoorthy, Suresh
    Nimje, Roshan Y.
    Jarugu, Lokesh Babu
    Chikkananjaiah, Nanjundaswamy Kanikahalli
    Reddy, China Anki
    Anjanappa, Prakash
    Botlagunta, Murali
    Vanteru, Sridhar
    Maddala, Nageswararao
    Shankar, Muniyappa
    Nair, Satheesh
    Hynes, John, Jr.
    Santella, Joseph B., III
    Carter, Percy H.
    Rampulla, Richard
    Vetrichelvan, Muthalagu
    Gupta, Anuradha
    Gupta, Arun Kumar
    Mathur, Arvind
    ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2019, 23 (05) : 912 - 918
  • [42] SYNTHESIS AND BIOLOGICAL-ACTIVITY OF SOME BASIC-SUBSTITUTED 4,9-DIHYDRO-3-METHYL-4-OXO-1H(2H)-PYRAZOLO[3,4-B]QUINOLINES
    RADL, S
    ZIKAN, V
    COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1988, 53 (08) : 1812 - 1819
  • [43] Synthesis, biological evaluation and modeling of hybrids from tetrahydro-1 H -pyrazolo[3,4-b ]quinolines as dual cholinestrase and COX-2 inhibitors
    Mroueh, Mohamed
    Faour, Wissam H.
    Shebaby, Wassim N.
    Daher, Costantine F.
    Ibrahim, Tamer M.
    Ragab, Hanan M.
    BIOORGANIC CHEMISTRY, 2020, 100
  • [44] (Z)-Ethyl 2-cyano-2-{2-[5,6-dimethyl-4-(thiophen-2-yl)-1H-pyrazolo[3,4-b]pyridin-3-yl]hydrazinylidene}acetate
    Fun, Hoong-Kun
    Hemamalini, Madhukar
    Abdel-Aziz, Hatem A.
    Aboul-Fadl, Tarek
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2011, 67 : O2145 - U1509
  • [45] SILICA SULFURIC ACID AS A SOLID ACID CATALYZED SYNTHESIS OF 4,5,6,7-TETRAHYDRO-2H-PYRAZOLO[3,4-b]PYRIDINE-5-CARBONITRILES AND 1,4-DIARYL-4,5-DIHYDRO-3-METHYL-1H-PYRAZOLO[3,4-b]PYRIDINE-6(7H)-ONES
    Mahdavinia, Gholam Hossein
    Rahmati, Abbas
    REVUE ROUMAINE DE CHIMIE, 2015, 60 (11-12) : 1025 - 1032
  • [46] 4-(4-Fluorophenyl)-3-methyl-6-oxo-1-phenyl-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile
    Wang, J
    Zhu, SL
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2006, 62 : O47 - O48
  • [47] 3′-Methyl-2-oxo-1′,5′-diphenyl-1′,7′-dihydrospiro[indoline-3,4′-pyrazolo[3,4-b]pyridine]-6′-carboxylic Acid
    Romo, Pablo E.
    Insuasty, Braulio
    Quiroga, Jairo
    Abonia, Rodrigo
    MOLBANK, 2021, 2021 (02)
  • [48] Unexpected formation of 4,5-dihydro-1H-pyrazolo[3,4-b]pyridine derivatives as a potent antitubercular agent and its evaluation by green chemistry metrics
    Jamale, D. K.
    Vibhute, S. S.
    Undare, S. S.
    Valekar, N. J.
    Patil, K. T.
    Warekar, P. P.
    Patil, P. T.
    Kolekar, G. B.
    Anbhule, P. V.
    SYNTHETIC COMMUNICATIONS, 2018, 48 (21) : 2750 - 2760
  • [49] Synthesis, Antibacterial and Antioxidant Evaluation of Novel 1-(5,7-Dichloro-1,3-benzoxazol-2-yl)-1H-pyrazolo[3,4-b]quinoline Derivatives
    Jayanna, N. D.
    Vagdevi, H. M.
    Dharshan, J. C.
    Kekuda, T. R. Prashith
    JOURNAL OF CHEMISTRY, 2013, 2013
  • [50] Synthesis and Crystal Structure of 3,7,7-Trimethyl-1-phenyl-4-(3-nitrophenyl)-4,5,6,7,8,9-hexahydro-1H-pyrazolo[3,4-b]quinoline-5(6H)-one
    XU Jia-Ning TU Shu-Jiang② JIANG Hong ZHANG Jin-Peng ZHU Xiao-Tong WANG Qian(Department of Chemistry
    Chinese Journal of Structural Chemistry, 2005, (02) : 209 - 213