Reaction of Salt 1 with Cyanoacetic Acid Hydrazide (2c) in Absolute Ethanol. A mixture of salt 1
4.08 g, 0.012 mol) and hydrazide 2c (2.37 g, 0.024 mol) was heated for 50 h in absolute ethanol (15 ml).
(
Solvent was distilled off and the residue was dissolved in water (10-12 ml) and extracted with toluene
3 × 15 ml). The toluene solution was dried using MgSO , solvent was distilled off, and the residue was
(
4
separated on a column (toluene–acetone, 4:1) to give compound 7c (0.85 g, 27%), compound 5 (0.28 g,12%),
and compound 6 (0.32 g, 13%). Distillation of solvent from the aqueous solution and preparative separation on a
column (toluene–acetone, 1:1) gave compound 8 (0.31 g, 16%). Mass spectrum of compound 8, m/z (I , %): 163
rel
(
100), 124 (10), 108 (16), 93 (11), 81 (10), 67 (9), 53 (7).
Reaction of Salt 1 with Hydrazide 2c in Water. A mixture of the salt 1 (4.08 g, 0.012 mol) and
hydrazide 2c (2.37 g, 0.024 mol) in water (15 ml) was heated for 25 h. After treatment by the method for
compounds 1 and 2b in ethanol the toluene solution gave compound 5 (0.21 g, 8%) and compound 7c (0.4 g,
1
3%) and the aqueous gave compound 9 (0.93 g, 40%) and compound 8 (0.07 g, 4%).
Reaction of Salt 1 with 4,6-Dimethyl-2-pyrimidinylacetic Acid Hydrazide (2e) in Absolute Ethanol.
A mixture of salt 1 (1.34 g, 0.004 mol) and hydrazide 2e (1.44 g, 0.008 mol) in absolute ethanol (7 ml) was
heated for 30 h at ~100°C. Solvent was distilled off and the residue was separated preparatively on a column
(
1
toluene–acetone, 1:1) to give compound 7e (0.35 g, 26%), compound 5 (0.12 g, 15%), compound 6 (0.09 g,
1%), and compound 8 (0.07 g, 11%). Mass spectrum of 2e, m/z (I , %): 339 (64), 294 (44), 293 (100), 267
rel
(
12), 266 (15), 112 (13), 42 (14), 28 (18), 18 (37).
Reaction of Salt 1 with Phenylacetic Acid Hydrazide (2d) in Absolute Ethanol. A solution of salt 1
2.04 g, 0.006 mol) and hydrazide 2d (1.8 g, 0.012 mol) in absolute ethanol (10 ml) was heated for 20 h.
(
Treatment similar to that of compounds 1 and 2e in absolute ethanol gave compound 7d (0.39 g, 21%),
compound 5 (0.14 g, 12%), compound 6 (0.12 g, 10%), and compound 8 (0.18 g, 18%).
Reaction of Salt 1 with Acetic Acid Hydrazide (2f) in Absolute Ethanol. A mixture of salt 1 (1.02 g,
0
.003 mol) and hydrazide 2f (0.44 g, 0.006 mol) in absolute ethanol (8 ml) was heated for 27 h at ~100°C.
Solvent was distilled off and the residue was successively washed with hexane and chloroform. Solvent was
removed from the hexane extract and the residue was separated on a column (hexane–acetone, 4:1) to give
compound 7f (0.7 g, 10%), compound 5 (0.09 g, 15%), and compound 6 (0.55 g, 9%). Distillation of solvent
from the chloroform extract and column chromatography of the residue (toluene–acetone, 2:1) gave compound 8
(
0.15 g, 31%).
Reaction of Salt 1 with Hydrazide 2f in Water. A solution of the iodide 1 (1.34 g, 0.004 mol) and
hydrazide 2f (0.66 g, 0.008 mol) in water (10 ml) was heated for 40 h, extracted with hexane and chloroform,
and worked up as for compounds 1 and 2f in absolute ethanol to give compound 5 (0.07 g, 9%) from the hexane
solution and compounds 8 (0.1 g, 15%) and 9 (0.39 g, 50%) from the chloroform solution.
Reaction of Salt 1 with Formic Acid Hydrazide 2g in Absolute Ethanol. A mixture of salt 1 (1.02 g,
0
.003 mol) and hydrazide 2g (0.44 g, 0.006 mol) in absolute ethanol (8 ml) was heated for 30 h at ~100°C.
Solvent was distilled off and the residue was washed with chloroform and preparatively separated on a column
hexane–acetone, 3:1) to give compound 5 (0.1 g, 13%), compound 6 (0.18 g, 22%), and compound 8 (0.32 g,
9%).
(
4
This work was carried out with the financial support of the Armenian National fund for Science and
Advanced Technology and the fund for US Civil Research and Development (NFSAT RA-US CRDF, grant
N CH 090-02 / 12040) and also within the scope of the Science Theme 0543 of the Armenian Republic Science
and Production Ministry.
The authors thank Professor Alan Katritzky (University of Florida, USA) for support and collaboration.
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