Synthesis of Azaheterocyclic Cymantrene Derivatives
- Authors: Potkin V.I.1, Petkevich S.K.1, Kletskov A.V.1, Kolesnik I.A.1, Dikusar E.A.1, Rozentsveig I.B.2, Levkovskaya G.G.2, Nasirova D.K.3, Borisova K.K.3, Zubkov F.I.3
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Affiliations:
- Institute of Physical Organic Chemistry
- Favorskii Irkutsk Institute of Chemistry, Siberian Branch
- Peoples’ Friendship University of Russia
- Issue: Vol 54, No 3 (2018)
- Pages: 452-462
- Section: Article
- URL: https://bakhtiniada.ru/1070-4280/article/view/217347
- DOI: https://doi.org/10.1134/S1070428018030132
- ID: 217347
Cite item
Abstract
The reduction of acetylcymantrene with sodium tetrahydridoborate gave cymantrenylethanol which was acylated with 4,5-dichloroisothiazole- and 5-(4-methylphenyl)isoxazole-3-carbonyl chlorides to obtain esters containing a 1,2-thia(oxa)zole fragment. The condensation of acetylcymantrene with 5-arylisoxazole-3- carbaldehydes, (5-arylisoxazol-3-yl)methoxybenzaldehydes (Ar = Ph, 4-Tol), and 4,5-dichloroisothiazole-3- carbaldehyde afforded the corresponding (E)-3-(azol-3-yl)-1-cymantrenylprop-2-en-1-ones. The resulting α,β- unsaturated ketones reacted with semicarbazide hydrochloride and thiosemicarbazide to produce substituted 4,5-dihydro-1H-pyrazole-1-carboxamides and -1-carbothioamides, and their reaction with hydroxylamine hydrochloride led to the formation of 4,5-dihydroisoxazoles containing cymantrene and 1,2-azole fragments. Heterocyclization of azolylcymantrenylpropenones with guanidine gave 2-aminopyrimidine derivatives, and dihydropyrimidine-2-thiones were obtained by their reaction with thiourea.
About the authors
V. I. Potkin
Institute of Physical Organic Chemistry
Author for correspondence.
Email: potkin@ifoch.bas-net.by
Belarus, ul. Surganova 13, Minsk, 220072
S. K. Petkevich
Institute of Physical Organic Chemistry
Email: potkin@ifoch.bas-net.by
Belarus, ul. Surganova 13, Minsk, 220072
A. V. Kletskov
Institute of Physical Organic Chemistry
Email: potkin@ifoch.bas-net.by
Belarus, ul. Surganova 13, Minsk, 220072
I. A. Kolesnik
Institute of Physical Organic Chemistry
Email: potkin@ifoch.bas-net.by
Belarus, ul. Surganova 13, Minsk, 220072
E. A. Dikusar
Institute of Physical Organic Chemistry
Email: potkin@ifoch.bas-net.by
Belarus, ul. Surganova 13, Minsk, 220072
I. B. Rozentsveig
Favorskii Irkutsk Institute of Chemistry, Siberian Branch
Email: potkin@ifoch.bas-net.by
Russian Federation, ul. Favorskogo 1, Irkutsk, 664033
G. G. Levkovskaya
Favorskii Irkutsk Institute of Chemistry, Siberian Branch
Email: potkin@ifoch.bas-net.by
Russian Federation, ul. Favorskogo 1, Irkutsk, 664033
D. K. Nasirova
Peoples’ Friendship University of Russia
Email: potkin@ifoch.bas-net.by
Russian Federation, ul. Miklukho-Maklaya 6, Moscow, 117198
K. K. Borisova
Peoples’ Friendship University of Russia
Email: potkin@ifoch.bas-net.by
Russian Federation, ul. Miklukho-Maklaya 6, Moscow, 117198
F. I. Zubkov
Peoples’ Friendship University of Russia
Email: potkin@ifoch.bas-net.by
Russian Federation, ul. Miklukho-Maklaya 6, Moscow, 117198
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