Synthesis, Structure, and Some Transformations of Novel 1,5-methanonaphtho[1,2-g][1,3,5]oxadiazocine Derivatives

Ivan V. Kulakov, Diana N. Ogurtsova, Tulegen M. Seilkhanov, Yuriy V. Gatilov, Alexander S. Fisyuk

Research output: Contribution to journalArticlepeer-review

Abstract

Biginelli reaction of thiourea, 2-hydroxy-1-naphthaldehyde, and acetoacetic ester (or benzoyl acetone) under solvent-free conditions and MW irradiation gave novel 3-thioxo-2,3,4,5-tetrahydro-1H-1,5-methanonaphtho[1,2-g][1,3,5]oxadiazocine derivatives. Subsequent reaction of the obtained compounds with α-chloroacetamide led to 5-methyl-5H,13H-5,13-methanonaphtho[1,2-g] thiazolo[2,3-d][1,3,5]oxadiazocin-1(2H)-ones, which were converted to the Z-isomers of 2-arylylidene-5H,13H-5,13-methanonaphtho[1,2-g]thiazolo[2,3-d][1,3,5]oxadiazocin-1(2H)-one derivatives by reaction with arylaldehydes. The structures of the products were characterized by 1H NMR, 13C NMR spectra, and X-ray analysis.

Original languageEnglish
Pages (from-to)923-928
Number of pages6
JournalJournal of Heterocyclic Chemistry
Volume55
Issue number4
DOIs
Publication statusPublished - 1 Apr 2018

Keywords

  • MITOTIC KINESIN INHIBITORS
  • SPINDLE BIPOLARITY
  • MONASTROL

Fingerprint Dive into the research topics of 'Synthesis, Structure, and Some Transformations of Novel 1,5-methanonaphtho[1,2-g][1,3,5]oxadiazocine Derivatives'. Together they form a unique fingerprint.

Cite this