1) Nukus Filial, Tashkent SAU, Nukus, 742009, ul. Kh. Abdambetova; 2) Complex Institute of Natural Sciences,
Karakalpak Division, Academy of Sciences of the Republic of Uzbekistan, Nukus, 742006, pr. Berdakha, 41. Translated from
Khimiya Prirodnykh Soedinenii, No. 6, pp. 446-447, November-December, 2004. Original article submitted May 26, 2003.
0009-3130/04/4006-0541
©
2004 Springer Science + Business Media, Inc.
541
1 - 4
NH
2
NH
2
OH
R
1
R
2
R
3
NNH
Het
5 - 8
5c, d, f, g,
Het = A;
6d, g,
Het = B;
7g,
Het = C;
8a, e, f, g, h,
Het = D
a:
R
1
= R
2
= R
3
= H;
c:
R
1
= R
3
=H, R
2
= CH
3
d:
R
1
= R
3
= H, R
2
= OMe;
e:
R
1
= R
3
= H, R
2
= Cl
f:
R
1
= R
2
= H, R
3
= Cl;
g:
R
1
= R
2
= H, R
3
= F
h:
R
1
= R
2
= Cl, R
3
= H
Het:
A =
O
O
Cl
O
O
Br
B =
C =
O
O
HOOC
O
O
Het
R
3
R
2
R
1
OH
O
Chemistry of Natural Compounds, Vol. 40, No. 6, 2004
SYNTHETIC ANALOGS OF NATURAL FLAVOLIGNANS.
XII.
*
SYNTHESIS OF 3,5-DIARYLSUBSTITUTED PYRAZOLINES BASED
ON 1,3-BENZODIOXANE AND 1,4-BENZODIOXANE CHALCONE ANALOGS
A. Aitmambetov,
1
Z. Yu. Ibragimova,
2
and A. Tokhtybaeva
2
UDC 547.814.5
3,5-Diarylsubstituted pyrazolines were synthesized by reaction of 1,3-benzodioxane and 1,4-benzodioxane
chalcone analogs with hydrazine hydrate. The structures of the products were confirmed by PMR
spectroscopy.
Key words:
chalcones, properties, hydrazine, pyrazoline.
2
′
-Hydroxychalcones, which have structures similar to many natural pigments containing polyhydroxy-
and polymethoxychalcones and related flavones and flavonols, are some of the most interesting derivatives of
β
-phenylacrylophenones. Chalcones are known to be convenient synthons for various heterocyclic compounds.
Pyrazoline derivatives possess various biological activity. Compounds characterized by antispasmodic, bactericidal,
fungicidal, antiestrogen, and therapeutic activity and monoamineoxidase inhibitors have been found among them [1].
In order to prepare new bioactive compounds, we studied the reaction of 1,3-benzodioxane and 1,4-benzodioxane
analogs of chalcone with hydrazine hydrate. Reaction of hydrazine hydrate with 1-4 [2-4] in alcohol at the boiling point of the
reaction mixture produced a pyrazoline ring to form 3-(2-hydroxyphenyl)-5-hetarylpyrazolines 5-8 [5].
______
*For part XI, see [6].