Synthesis of new triazolo[1,5-b][2,4]benzodiazepines via tandem cyclization of o-(azidomethyl)benzoates with cyanoacetamides

被引：2
作者：
Yakovenko, Georgiy G. [1 ]
Yagodkina, Marta S. [1 ]
Bol'but, Andriy V. [1 ,2 ]
Shishkina, Svitlana V. [3 ,4 ]
Vovk, Mykhailo V. [1 ]
机构：
[1] Natl Acad Sci Ukraine, Inst Organ Chem, 5 Murmanska Str, UA-02660 Kiev, Ukraine
[2] RPA Enamine, 78 Chervonotkatska Str, UA-02660 Kiev, Ukraine
[3] Natl Acad Sci Ukraine, STC Inst Single Crystals, 60 Nauky Ave, UA-61001 Kharkov, Ukraine
[4] VM Karasin Kharkiv Natl Univ, Dept Inorgan Chem, 4 Svobody Sq, UA-61122 Kharkov, Ukraine
来源：
MONATSHEFTE FUR CHEMIE | 2017年 / 148卷 / 06期
关键词：
Heterocycles; NMR spectroscopy; Crystal structure; Annelation; X-ray structure determination; BIOLOGICAL EVALUATION; RECEPTOR ANTAGONISTS; BENZODIAZEPINES; DERIVATIVES; INHIBITORS; ANXIETY; TRANSFORMATIONS; 1,4-DIAZEPINES; DISORDERS; ESTAZOLAM;
D O I：
10.1007/s00706-016-1905-5
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Based on the tandem anionic cyclization of o-(azidomethyl)benzoates with 2-cyanoacetamides, an efficient synthetic route to the hitherto unknown heterocyclic system, triazolo[1,5-b][2,4]benzodiazepine, has been developed. The optimum reaction conditions have been found which provide 59-74% yields of target compounds. Their structural determination has been performed by the IR, LCMS, and NMR spectral methods as well as by X-ray diffraction analysis.
引用
收藏
页码：1035 / 1041
页数：7
相关论文
共 56 条
  • [1] Synthesis of N-substituted γ-methylene γ-lactams
    Adhikari, R
    Jones, DA
    Liepa, AJ
    Nearn, RH
    [J]. AUSTRALIAN JOURNAL OF CHEMISTRY, 2005, 58 (12) : 882 - 890
  • [2] A new modular and flexible approach to [1,2,3]triazolo[1,5-a][1,4]benzodiazepines
    Alajarin, Mateo
    Cabrera, Jose
    Pastor, Aurelia
    Villalgordo, Jose M.
    [J]. TETRAHEDRON LETTERS, 2007, 48 (20) : 3495 - 3499
  • [3] Ligands to the (IRAP)/AT4 receptor encompassing a 4-hydroxydiphenylmethane scaffold replacing Tyr2
    Andersson, Hanna
    Demaegdt, Heidi
    Vauquelin, Georges
    Lindeberg, Gunnar
    Karlen, Anders
    Hallberg, Mathias
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2008, 16 (14) : 6924 - 6935
  • [4] Synthesis of DNA-Interactive Pyrrolo[2,1-c][1,4]benzodiazepines (PBDs)
    Antonow, Dyeison
    Thurston, David E.
    [J]. CHEMICAL REVIEWS, 2011, 111 (04) : 2815 - 2864
  • [5] New Insight into the Central Benzodiazepine Receptor-Ligand Interactions: Design, Synthesis, Biological Evaluation, and Molecular Modeling of 3-Substituted 6-Phenyl-4H-imidazo[1,5-a][1,4]benzodiazepines and Related Compounds
    Anzini, Maurizio
    Valenti, Salvatore
    Braile, Carlo
    Cappelli, Andrea
    Vomero, Salvatore
    Acaro, Stefano
    Ortuso, Francesco
    Marinelli, Luciana
    Limongelli, Vittorio
    Novellino, Ettore
    Betti, Laura
    Giannaccini, Gino
    Lucacchini, Antonio
    Daniele, Simona
    Martini, Claudia
    Ghelardini, Carla
    Mannelli, Lorenzo Di Cesare
    Giorgi, Gianluca
    Mascia, Maria Paola
    Biggio, Giovanni
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2011, 54 (16) : 5694 - 5711
  • [6] 1,5-Benzothiazepine, a versatile pharmacophore: A review
    Bariwal, Jitender B.
    Upadhyay, Kuldip D.
    Manvar, Atul T.
    Trivedi, Jalpa C.
    Singh, Jyoti S.
    Jain, Kishor S.
    Shah, Anarmik K.
    [J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2008, 43 (11) : 2279 - 2290
  • [7] Enols of substituted cyanomalonamides
    Basheer, Ahmad
    Yamataka, Hiroshi
    Ammal, Salai Cheettu
    Rappoport, Zvi
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (14) : 5297 - 5312
  • [8] Docking of 1,4-Benzodiazepines in the α1/α2 GABAA Receptor Modulator Site
    Berezhnoy, D.
    Gibbs, T. T.
    Farb, D. H.
    [J]. MOLECULAR PHARMACOLOGY, 2009, 76 (02) : 440 - 450
  • [9] Substituted 1,2,3-triazolo[1,5-a]quinazolines: synthesis and binding to benzodiazepine and adenosine receptors
    Bertelli, L
    Biagi, G
    Giorgi, I
    Livi, O
    Manera, C
    Scartoni, V
    Lucacchini, A
    Giannaccini, G
    Barili, PL
    [J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2000, 35 (03) : 333 - 341
  • [10] CHOLECYSTOKININ ANTAGONISTS - SYNTHESIS AND BIOLOGICAL EVALUATION OF 4-SUBSTITUTED 4H-[1,2,4]TRIAZOLO[4,3-A][1,4]BENZODIAZEPINES
    BOCK, MG
    DIPARDO, RM
    EVANS, BE
    RITTLE, KE
    VEBER, DF
    FREIDINGER, RM
    CHANG, RSL
    LOTTI, VJ
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1988, 31 (01) : 176 - 181
123456