Phenyl isothiocyanate reacts with 2-cyanoacetohydrazide (1) to yield the corresponding 1-cyanoacetyl-4-phenylthiosemicarbazide (3), via acid hydrolysis of the intermediate 2 whereas cyclization of 3 gave the 1,2,4-triazoles 4, 1,3,4-thiadiazoles 7 and 1,3,4-thiadiazine-5-ones 9; compound 4a was reacted with phenyl isothiocyanate, dicyandiamide, sulfanylacetic acid and benzaldehyde to afford 11, 13, 14 and 15, respectively.
References
1.
DoboszM., RekasJ., and PachutaA., Acta Pol. Pharm., 1989, 46, 40.
2.
DoboszM., PachutaA., and RekasJ., Acta Pol. Pharm., 1993, 50, 225.
3.
BrucatoA., CoppolaA., GianguzzaS., and ProvenzanoP. M., Boll-Soc. Ital. Biol. Sper., 1978, 54, 1051.
4.
CoffenD. L., and FryerR. I., US Pat., 3849434, 1974.
5.
ShirokiM., TaharaT., and ArakiK., Jpn. Pat., 75100096, 1975.
6.
PovelitsaF. D., and GuralA. G., Antibiotiki (Moscow), 1973, 18, 71.
7.
MirI., and SiddiquiM. T., Tetrahedron, 1970, 26, 5235.
8.
GascoA., MortariniV., and ReynaudE., Farmaco Ed. Sci., 1973, 28, 624.
9.
HamodaY., MatsunoT., IshiiT., ImaiK., and ManoM., Jpn. Pat., 7563119, 1975.
10.
De MarinisR. M., HooverJ. R. E., DunnG. L., ActorP., UriJ. V., and WeisbachJ. A., J. Antibiot., 1975, 28, 463.
11.
MekheimerR., J. Chem. Res. (S), 1994, 304.
12.
MekheimerR., Bul. Soc. Chim. Fr., 1994, 131, 279.
13.
ShakerR. M., Die Pharm., 1996, 148.
14.
MekheimerR., ShakerR. M., SadekK. U., and OttoH. H., Heterocycl. Commun., 1997, 3, 217.
15.
ShakerR. M., and Abdel-LatifF. F., J. Chem. Res. (S), 1997, 294.
16.
MoharebR. M., and SherifS. M., Sulfur Lett., 1992, 15(1), 91.
17.
ElmoghayarM. R. H., GhaliE. A., RamizM. M. M., and ElnagdiM. H., Liebigs Ann. Chem., 1985, 1962.
18.
KatritzkyA. R., BorowieckaJ., FanW.-Q., and BranniganL. H., J. Heterocycl. Chém., 1991, 28, 1139.
19.
MariaD., and AnnaP.-S., Acta Pol. Pharm., 1995, 52, 103.
