TRANSFORMATION OF 4-ARYL(HETERYL)-2,6-DIAMINO-3,5-DICYANO-4Í-THIOPYRANS
733
5.966.16 m (1H, =CH), 7.12 d (2Harom, J 8.88 Hz),
7.66 d (1Harom, J 8.42 Hz), 8.04 s (1Harom), 8.21 m
(2Harom), 8.22 m (2Harom), 8.35 s (1H, C3H=). Found,%:
C 60.88; H 3.22; N 6.67. C21H14Cl2N2OS. Calculated,%:
C 61.03; H 3.41; N 6.78.
2. Elnagdi, M., Harb, A.F.A., Elghandour, A.H.H., Hus-
sien,A.H.M., and Metwally, S.A.M., Gazz. Chim. Ital., 1992,
vol. 122, p. 299; Fathy, F.A.-L., Bull. Chem. Soc. Jpn., 1989,
vol. 62, p. 3768; Elnagdi, M. and Erian, A.W., Bull. Soc.
Chim.,1995, vol. 132, p. 920; Frolova, N.G., Zavyalo-
va, V.K., and Litvinov, V.P., Abstracts of Papers, 19 Vse-
rossiiskoi Konf. Org. Khim. Tekhnol. Org. Soedin. Sery
(19th Conf. on Organic Chemistry and Technology of
Organic Compounds of Sulfur), Kazan, 1995, Ch. I, p. 13;
Frolova, N.G., Zavyalova, V.K., and Litvinov, V.P., 12th
Symp. Chem. Heterocyclic Comp. and 6th Blue Danube
Symp. Heterocyclic Chem., Brno, 1996, p. 45; Frolo-
va, N.G., Zavyalova, V.K., and Litvinov, V.P., Izv. Akad.
Nauk, Ser. Khim., 1996, p. 938.
3-(4-Carbamoylmethoxy)-2-[4-(3,4-dichloro-
phenyl)thiazol-2-yl]acrylonitrile (XV) was prepared
in the same way as compound XIII using nitrile IVy and
amide VIId. Yield 3.49 g (81%), mp 213214°C. IR
1
1
spectrum, cm : 2187 (CºN), 1682 (C=O). H NMR
spectrum, d, ppm: 4.53 s (2H, CH2), 7.14 d and 8.05 d
(2H each, C6H4, J 8.56 Hz), 7.36 br.s (2H, NH2), 7.60 d
(1Harom, J 8.58 Hz), 7.98 c (1Harom), 8.25 m (3Harom and
C3H=). Found,%: C 55.70; H 2.89; N 9.64.
C20H13Cl2N3O2S. Calculated,%: C 55.83; H 3.05; N 9.77.
3. Shestopalov, A.M., Mortikov, V.Yu., Nesterov, V.N.,
Sharanin, Yu.A., Promonenkov, V.K., and Litvinov, V.P., Izv.
Akad. Nauk SSSR, Ser. Khim., 1984, p. 2409; Promonen-
kov, V.K., Sharanin, Yu.A., Goncharenko, M.P.,
Shestopalov, A.M., and Melenchuk, S.N., Abstracts of
Papers, Vsesoyuz. soveshch. Khimiya i tekhnologiya
geterokumulenov dlya proizvodstva KhSZR (All-Union
Meeting on Chemistry and Technology of Heterocou-
mulenes for Production of Chemical Preparations of Plant
Protection), Moskva, 1985, p. 57; Sharanin, Yu.A.,
Shestopalov, A.M., Litvinov, V.P., Mortikov, V.Yu.,
Rodinovskaya, L.A., Goncharenko, M.P., and Promo-
nenkov, V.K., Zh. Or. Khim., 1986, vol. 22, p. 1962; Shara-
nin, Yu.A., Shestopalov, A.M., Mortikov, V.Yu., Melen-
chuk, S.N., Promonenkov, V.K., Zolotarev, B.M., and
Litvinov, V.P., Izv. Akad. Nauk SSSR, Ser. Khim., 1986,
p. 1512; Sharanin, Yu.A., Promonenkov, V.K., Litvinov, V.P.,
Shestopalov,A.M., Mortikov, V.Yu., and Demerkov, A.S.,
Vsesoyuz. soveshch. Khimiya i tekhnologiya getero-
kumulenov dlya proizvodstva KhSZR (All-Union
Meeting on Chemistry and Technology of
Heterocoumulenes for Production of Chemical
Preparations of Plant Protection), Moskva, 1985, p. 49.
4. Dyachenko, V.D., Krivokolysko, S.G., Nesterov, V.N., and
Litvinov, V.P., Khim. Geterotsikl. Soedin., 1997, p. 1677;
Dyachenko, V.D., Krivokolysko, S.G., and Litvinov, V.P.,
Khim. Geterotsikl. Soedin., 1996, p. 1099; Sharanin, Yu.A.,
Promonenkov, V.K., Litvinov, V.P., and Shestopalov,A.M.,
Abstracts of Papers, Vsesoyuzn. konf. Khimiya i
tekhnologiya piridinsoderzhashchikh pestitsidov
(Chemistry and Technology of Contaning Pyridines
Pesticides), Chernogolovka, 1988, p. 116; Elnagdi, M.H.,
Ghozian, S.A.S., Abdelrazek, F.M., and Selim, M.A.,
J. Chem. Res., C, 1991, p. 116; Promonenkov, V.K.,
Otochevannaya, S.V., Zavyalova, V.K., Litvinov, V.P., and
Sharanin, Yu.A., Abstracts of Papers, Vsesoyuzn. konf.
3-(4-Benzyloxyphenyl)-2-[4-(4-biphenyl)thiazol-
2-yl]acrylonitrile (XVI) was prepared in the same way
as compound XIII using chloride VIIb and nitrile IVz2.
1
Yield 3.72 g (79%), mp 158159°C. IR spectrum, cm :
1
2185 (CºN). H NMR spectrum, d, ppm: 5.24 s (2H,
CH2), 7.24 d (2Harom, J 8.15 Hz), 7.327.63 m (8Harom),
7.697.75 m (4Harom), 7.78 s (1H, H5thiazole), 8.05 d
(2Harom, J 8.19 Hz), 8.14 d (2Harom, J 7.99 Hz), 8.27 s
(1H, C3H=). Found,%: C 78.95; H 4.60; N 6.13.
C31H22N2OS. Calculated,%: C 79.12; H 4.71; N 5.95.
3-(4-Benzyloxyphenyl)-2-[4-cyclopropylthiazol-2-
yl]acrylonitrile (XVII) was prepared in the same way
as compound XIII using chloride VIIb and nitrile IVz.
1
Yield 3.19 g (89%), mp 113115°C. IR spectrum, cm :
1
2189 (CºN). H NMR spectrum, d, ppm: 0.95 m (4H,
2CH2), 2.08 m (1H, H1cyclopropane), 5.19 s (2H, CH2O),
7.12 d and 7.95 d (2H each, C6H4, J 8.94 Hz), 7.17 s
(1H, H5thiazole), 7.317.46 m (5H, Ph), 8.02 s (1H, C3H=).
Found,%: C 73.59; H 4.88; N 8.01. C22H18N2OS.
Calculated,%: C 73.72; H 5.06; N 7.82.
3-(4-Benzyloxyphenyl)-2-[4-(4-chlorophenyl)-
thiazol-2-yl]acrylonitrile (XVIII) was prepared in the
same way as compound XIII using chloride VIIb and
nitrile IVx. Yield 3.26 g (76%), mp 221223°C. IR
1
spectrum, cm : 2193 (CºN). 1H NMR spectrum, d, ppm:
4.28 s (2H, CH2), 6.94 d (2Harom, J 8.11 Hz), 7.51 d
(2Harom, J 8.72 Hz), 7.67 d (2Harom, J 7.69 Hz), 7.85
8.11 m (7Harom), 8.19 s (1H, H5thiazol), 8.22 s (1H, C3H=).
Found,%: C 69.84; H 3.91; N 6.39. C25H17ClN2OS.
Calculated,%: C 70.00; H 4.00; N 6.53.
REFERENCES
1. Matrosova, S.V., Zavyalova, V.K., Litvinov, V.P., and
Sharanin, Yu.A., Izv. Akad. Nauk SSSR, Ser. Khim., 1991,
p. 1643.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 42 No. 5 2006