FEATURES OF THE REACTIONS OF β-ARYL(HETERYL)-α-NITROACRYLATES
was heated for 3 h. Then the solvent was evaporated in
ACKNOWLEDGMENTS
1407
a Petri dish. The residue was treated with ethanol.
Yield 0.03 g (38%), mp 108–110°C (ethanol). For both
samples the melting point depression was not
observed.
This work was supported by the Government of St.
Petersburg (diploma no. 11036).
REFERENCES
1. Perekalin, V.V., Lipina, E.S., Berestovitskaya, V.M.,
and Efremov, D.A., Nitroalkenes. Conjgated Nitro
Compounds, London: John Wiley and Sons, 1994.
2-(4-N,N-Dimethylaminophenyl)benzothiazole
(XXIII). To a solution of 0.26 g (1 mmol) of ethyl 3-
(4-N,N-dimethylaminophenyl)-2-nitropropenoate III in
10 ml of anhydrous methanol was added 0.13 g
(1 mmol) of o-aminothiophenol. The reaction mixture
was kept at room temperature for 1 day. Then the
solvent was removed on a rotary evaporator, and the
residue was treated with diethyl ether. Yield 0.07 g
(29%), mp 150–152°C (ethanol) {mp 154–156°C [29]}.
2. Ono, N., The Nitro Group in Organic Synthesis, New
York: Wiley-VCH, 2001, 372 p.
3. Perekalin, V.V. and Temp, A.A., USSR Author’s
Certificte no. 209465, 1968; Bull. Izobret., 1968, no. 5,
p. 33.
4. Zen, S. and Umezawa, S., Bull. Chem. Soc. Japan,
1963, vol. 36, no. 9, p. 1146.
2-(4-Nitrophenyl)benzothiazole (XXIV). a. To a
suspension of 0.27 g (1 mmol) of ethyl 2-nitro-3-(4-
nitrophphenyl)propenoate IV in 5 ml of the anhydrous
methanol was added 0.13 g (1 mmol) of o-amino-
thiophenol. The reaction mixture was kept at 16–18°C
for 1 h. Then the solution was poured into the crushed
ice, and the resulting yellow precipitate was filtered
off. Yield 0.06 g (21%), mp 240–242°C (benzene)
{mp 240–242°C [30]}.
5. Aboskalova, N.I., Gaukhberg, R.D., Zhitnyuk, T.M.,
Polyanskaya, A.S., Perekalin, V.V., and Samarina, I.B.,
Book of Abstracts, XXXI Gertsenovskikh chtenii
“Metody sinteza, stroenie
i
khimicheskie prev-
rashcheniya nitrosoedinenii” (XXXI Herzen Meeting
“Methods of Synthesis, Structure, and Chemical
Transformations of Nitro Compounds”), Leningrad,
1978, p. 86.
6. Aboskalova, N.I., Berestovitskaya, V.M., Bakhareva, S.V.,
and Fel’gendler, A.V., Chem. Heterocyclic Chem.,
2002, no. 10, p. 1291.
b. To a solution of 0.27 g (1 mmol) of ethyl 2-nitro-
3-(4-nitrophenyl)propenoate IV in 7 ml of acetic acid
was added 0.13 g (1 mmol) of o-aminothiophenol. The
reaction mixture was kept at 16–18°C for 2 days. Then
0.08 g of yellow crystals was filtered off. Additionally
0.07 g of the crystals of XXIV was isolated from the
mother liquor. The overall yield is 0.15 g (59%), mp
244–246°C (benzene). For both samples the melting
point depression was not observed.
7. Aboskalova, N.I., Smirnova, N.N., Kataeva, O.N.,
Baichurin, R.I., Fel’gendler, A.V., Berkova, G.A., and
Berestovitskaya, V.M., Russ. J. Gen. Chem., 2008,
vol. 78, no. 9, p. 1479.
8. Azarifar, D., Pirhayati, M., Maleki, B., Sanginabadi, M.,
and Yami, R.N., J. Serb. Chem. Soc., 2010, vol. 75,
no. 9, p. 1181.
9. Zhang, L.-J., Xia, J., Zhou, Y.-Q., Wang, H., and
Wang, S.-W., Synth. Commun., 2012, vol. 42, no. 3,
p. 328.
2-(2-Furyl)benzothiazole (XXV). The freshly
prepared crystalline compound XX was kept for
2 weeks at room temperature at 16–18°C. The solid
gradually becomes oily. The resulting mixture was
treated with ethanol. mp 94–96°C (ethanol) {mp 98°C
[31]}.
10. Das Sharma, S. and Konwar, D., Synth. Commun., 2009,
vol. 39, no. 6, p. 980.
11. Ma, H., Wang, Y., Li J., and Wang, J., Heterocycles,
2007, vol. 71, no. 1., p. 135.
12. Reddy, L.S., Reddy, N.C.G., Reddy, T.R., Lingappa, Y.,
and Monah, R.B., J. Korean Chem. Soc., 2011, vol. 55,
no. 2, p. 304.
2-(2-Thienyl)benzothiazole (XXVI). To a solution
of 0.46 g (2 mmol) of ethyl 2-nitro-3-(2-thienyl)
propenoate VI in 10 ml of the anhydrous methanol was
added 0.25 g (2 mmol) of o-aminothiophenol. The
reaction mixture was kept at room temperature at 16–
18°C for 3 days. Then the solvent was evaporated on a
rotary evaporator, and the residue was treated with
ethanol. Yield 0.12 g (26%), mp 89–91°C (ethanol)
{mp 91–93°C [30]}. Found N, %: 6.02. C11H7NS2.
Calculated N, %: 6.45.
13. Bahrami, K., Khobaei, M.M., and Nejati, A., Green
Chem., 2010, vol. 12, no. 7, p. 1237.
14. Wan, J.-P., Gan, S.-F., Wu, J.-M., and Pan, Y., Green
Chem., 2009, vol. 11, no. 10, p. 1633.
15. Smith, J.G. and Ho, I., Tetrahedron Lett., 1971, vol. 12,
no. 38, p. 3541.
16. Baichurin, R.I., Aboskalova, N.I., and Berestovitskaya, V.M.,
Russ. J. Org. Chem., 2010, vol. 46, no. 10, p. 1590.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 82 No. 8 2012