Abstract
A one-pot procedure was developed for the synthesis of 3-isothiocyanatopropionaldehyde and 3-isothiocyanatobutyraldehyde diethyl acetals from the corresponding α,β-unsaturated aldehydes. Reactions of 1,1-diethoxy-3-isothiocyanatobutane with aliphatic amines and hydrazines gave, respectively, substituted thioureas and thiosemicarbazides which underwent acid-catalyzed cyclization to form 6-ethoxytetrahydropyrimidine-2(1H)-thiones, 9,10-dimethoxy-2-methyl-1,2,3,6,7,11b-hexahydro-4H-pyrimido[6,1-a]isoquinoline-4-thiones, and 2-methyl-2,3,6,7,12,12b-hexahydropyrimido[1′,6′:1,2]pyrido[3,4-b]indole-4(1H)-thione.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Verma, R.P., Phosphorus, Sulfur, Silicon Relat. Elem., 2003, vol. 178, p. 365.
Ignatova, L.A., Shutalev, A.D., Shingareeva, A.G., Dymova, S.F., and Unkovskii, B.V., Khim. Geterotsikl. Soedin., 1985, p. 260.
Fisyuk, A.S., Berdovich, L.V., Temnikov, D.V., and Knyaz’kova, L.N., Khim. Geterotsikl. Soedin., 1997, p. 921.
Peretokin, A.V., Shutalev, A.D., Mergenova, V.V., Chupin, A.M., Ignatova, L.A., Malina, Yu.F., and Unkovskii, B.V., Zh. Org. Khim., 1985, vol. 21, p. 1004.
Shutalev, A.D., Pagaev, M.T., and Ignatova, L.A., Zh. Org. Khim., 1991, vol. 27, p. 1274.
Fisyuk, A.S. and Mukanov, A.Yu., Khim. Geterotsikl. Soedin., 2003, p. 307.
Author information
Authors and Affiliations
Additional information
Original Russian Text © A. S. Fisyuk, A. Yu. Mukanov, 2006, published in Zhurnal Organicheskoi Khimii, 2006, Vol. 42, No. 9, pp. 1291–1296.
Rights and permissions
About this article
Cite this article
Fisyuk, A.S., Mukanov, A.Y. Synthesis of 3-isothiocyanatopropion-and-butyraldehyde diethyl acetals and their reactions with n-nucleophiles. Russ J Org Chem 42, 1269–1274 (2006). https://doi.org/10.1134/S107042800609003X
Received:
Issue Date:
DOI: https://doi.org/10.1134/S107042800609003X