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Synthesis, Structure, and Some Transformations of Novel 1,5‐methanonaphtho[1,2‐ g ][1,3,5]oxadiazocine Derivatives
Author(s) -
Kulakov Ivan V.,
Ogurtsova Dia.,
Seilkhanov Tulegen M.,
Gatilov Yuriy V.,
Fisyuk Alexander S.
Publication year - 2018
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.3119
Subject(s) - chemistry , thiourea , acetone , carbon 13 nmr , solvent , proton nmr , medicinal chemistry , organic chemistry
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‐1 H ‐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.