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

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

Journal

Journal of Heterocyclic Chemistry
ISSN: 0022-152X

Output data

Year: 2018, Volume: 55, Number: 4, Pages: 923-928 Pages count : 6 DOI: 10.1002/jhet.3119

Authors

Kulakov Ivan V. ¹ , Ogurtsova Diana N. ¹ , Seilkhanov Tulegen M. ² , Gatilov Yuriy V. ^3,4 , Fisyuk Alexander S. ^1,5

Affiliations

1	(Данные Web of science) Omsk FM Dostoevsky State Univ, Dept Organ Chem, 55a Mira Ave, Omsk 644077, Russia
2	(Данные Web of science) Sh Ualikhanov Kokshetau State Univ, 76 Abaya St, Kokshetau 020000, Kazakhstan
3	(Данные Web of science) Russian Acad Sci, Siberian Branch, NN Vorozhtsov Novosibirsk Inst Organ Chem, 9 Akad Lavrientieva Ave, Novosibirsk 630090, Russia
4	(Данные Web of science) Novosibirsk State Univ, 2 Pirogov St, Novosibirsk 630090, Russia
5	(Данные Web of science) Omsk State Tech Univ, Lab New Organ Mat, 11 Mira Ave, Omsk 644050, Russia

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 a-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.

Kulakov I.V. , Ogurtsova D.N. , Seilkhanov T.M. , Gatilov Y.V. , Fisyuk A.S.
Synthesis, Structure, and Some Transformations of Novel 1,5-methanonaphtho[1,2-g][1,3,5]oxadiazocine Derivatives
Journal of Heterocyclic Chemistry. 2018. V.55. N4. P.923-928. DOI: 10.1002/jhet.3119 WOS Scopus РИНЦ OpenAlex

Published online:	Feb 9, 2018
Published print:	Apr 1, 2018

Web of science:	WOS:000430179800017
Scopus:	2-s2.0-85041721298
Elibrary:	35485462
OpenAlex:	W2791105809

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