Contrasting behaviour of NBS towards 1,4-dihydrobenzothieno[3,2-b]pyridine 5,5-dioxides and 4,5-dihydro-1H-indeno[1,2-b]pyridines

Brigita Cekavicus, Brigita Vigante, Martins Rucins, Kintija Birkmane, Marina Petrova, Sergey Belyakov, Liga Zuka, Aiva Plotniece, Karlis Pajuste, Marina Gosteva, Arkadij Sobolev

Research output: Contribution to journalArticlepeer-review

4 Citations (Scopus)


Polycyclic 1,4-dihydrobenzothieno[3,2-b]pyridine 5,5-dioxides and 4,5-dihydro-1H-indeno[1,2-b]pyridines having ester or cyano group at the position 3 of dihydropyridine ring have been synthesised. Reactivity of N-bromosuccinimide (NBS) towards polycyclic 1,4-dihydropyridine derivatives has been investigated. It has been found that 1,4-dihydrobenzothieno[3,2-b]pyridine 5,5-dioxides are easily oxidised with NBS in methanol at rt in high yields, whereas 4,5-dihydro-1H-indeno[1,2-b]pyridines in reaction with NBS in methanol are brominated at 4a position affording stable 4a-bromo-4a,5-dihydroindeno[1,2- b]pyridine-3-carboxylates or unstable 3-carbonitriles, which rapidly undergo dehydrobromination reaction leading to the corresponding 5H-indeno[1,2-b] pyridine-3-carbonitriles.

Original languageEnglish
Pages (from-to)5550-5557
Number of pages8
Issue number26
Publication statusPublished - 1 Jul 2013
Externally publishedYes


  • Bromination
  • Cyclisation
  • N-Bromosuccinimide
  • Oxidation
  • Polycyclic 1,4-dihydropyridines

Field of Science*

  • 1.4 Chemical sciences
  • 3.1 Basic medicine

Publication Type*

  • 1.1. Scientific article indexed in Web of Science and/or Scopus database


Dive into the research topics of 'Contrasting behaviour of NBS towards 1,4-dihydrobenzothieno[3,2-b]pyridine 5,5-dioxides and 4,5-dihydro-1H-indeno[1,2-b]pyridines'. Together they form a unique fingerprint.

Cite this