tailieunhanh - Regioselective synthesis of bicyclic 1,3,5-triazepine system starting from tetrachloro-2-aza-1,3-butadienes

Readily available tetrachloro-2-aza-1,3-butadienes enter into directed cyclocondensation reaction with N-phenyl-1,2-cyclopentanediamine which leads to regioselective cyclopentane annulation by the 1,3,5-triazepine. | Regioselective synthesis of bicyclic 1 3 5-triazepine system starting from tetrachloro-2-aza-1 3-butadienes Current Chemistry Letters 6 2017 49 54 Contents lists available at GrowingScience Current Chemistry Letters homepage Regioselective synthesis of bicyclic 1 3 5-triazepine system starting from tetrachloro-2-aza-1 3-butadienes Bohdan A. Demydchuka Eduard B. Rusanovb Julia A. Rusanovac and Volodymyr S. Brovaretsa a Institute of Bioorganic Chemistry and Petrochemistry National Academy of Sciences of Ukraine Murmanska str. 1 02094 Kyiv Ukraine b Institute of Organic Chemistry National Academy of Sciences of Ukraine Murmanska str. 5 02094 Kyiv Ukraine c Department of Chemistry Taras Shevchenko National University Volodymyrska Str. 64 13 Kyiv 01601 Ukraine CHRONICLE ABSTRACT Article history Readily available tetrachloro-2-aza-1 3-butadienes enter into directed cyclocondensation Received August 21 2016 reaction with N-phenyl-1 2-cyclopentanediamine which leads to regioselective cyclopentane Received in revised form annulation by the 1 3 5-triazepine. The formation of the 1 3 5-triazepine derivatives was October 24 2016 confirmed proved by 1H- and 13C-NMR spectral study elemental analysis and in one case Accepted 15 February 2017 single-crystal x-ray crystallographic study. Available online 15 February 2017 Keywords Tetrachloro-2-aza-1 3-butadienes N-phenyl-1 2cyclopentanediamine 1 3 5-triazepine regioselective annulation 2017 Growing Science Ltd. All rights reserved. 1. Introduction 1 3 5-Triazepines and their derivatives are found to be associated with various biological activities antibacterial antiviral psychotropic activity 1 2 CCK2 receptor antagonists 3 phospholipase A2 inhibitors 4 HIV capsid assembly However information about hydrogenated 1 3 5- triazepine derivatives is very limited. Thus due to the difficulty of such structures obtaining 6 7- dihydro-1Н-1 3 5-triazepines are presented by only two The .