Synthesis of Azaheterocyclic Cymantrene Derivatives


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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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