2(5H)-furanone in the Vilsmeier - Haak reaction. Synthesis of β-substituted furans. Molecular structures of 3-dimethylaminomethylene-5-formyl-2(3H)-furanone and dimethylammonium 3,5-di(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidenemethyl)-2-furanolate

被引：0

作者：

Krapivin G.D. ^{[1
]}

Kozhina N.D. ^{[1
]}

Chernousenko L.A. ^{[1
]}

Zavodnik V.E. ^{[1
]}

机构：

[1] Kuban State Technological University

来源：

Chemistry of Heterocyclic Compounds | 1999年 / 35卷 / 1期

关键词：

Potassium; Hydrolysis; Organic Chemistry; Molecular Structure; Diffraction Analysis;

D O I：

10.1007/BF02251656

中图分类号：

学科分类号：

摘要：

The reaction of 2(5H)-furanone with the Vilsmeier - Haak - Arnold reagent and subsequent addition of concentrated aqueous HClO4 to the reaction mixture give (3-dimethylaminomethylen-2-oxo-3H-5-ßtranyl)melhylenimmonium perchlorate, whose hydrolysis under various conditions leads to 3-dimethylaminomethylene-5-formyl-2(3H)-furanone or to the potassium salt of 5-hydroxy-2,4-furandicarbaldehyde. The reaction of these products with CH-acids was studied. The structures of the key compounds of this work have been proved by the method of X-ray diffraction analysis. ©1999 KluwerAcademic/Plenum.

引用

页码：23 / 32

页数：9

共 15 条

[1] Kozhina N.D., Krapivin G.D., Zavodnik V.E., Gratsza T., Vegh D., Chernousenko L.A., Badovskaya L.A., Khim. Geterotsikl. Soedin., 1, (1995)
[2] Sorotskaya L.N., Badovskaya L.A., Kaklyugina T.Ya., Belen'kii L.I., Ignatenko A.V., Krutoshikova A., Pantseva L.A., Zh. Org. Khim., 25, (1989)
[3] Muzychenko G.F., Glukhovtsev V.G., Badovskaya L.A., Kozhina N.D., Ignatenko A.V., Kravchenko O.B., Nikitin G.I., Zh. Org. Khim., 17, (1981)
[4] Yoshii E., Koizumi N., Kitatsuji E., Heterocycles, 4, (1976)
[5] Vilsmeier A., Haak A., Ber., 60, (1927)
[6] Kira M.A., Nofal Z.M., Gadolla K.Z., Tetrahedron Lett., 48, (1970)
[7] Kiyomi K., Ichino M., J. Org. Chem., 37, (1972)
[8] Kitaigorodskii A.I., Zorkii P.M., Bel'skii V.K., Structure of Organic Compounds (Structural Data 1971-1973) [in Russian], (1982)
[9] Krapivin G.D., Val'ter N.I., Zavodnik V.E., Kaklyugina T.Ya., Kul'nevich V.G., Khim. Geterotsikl. Soedin., 3, (1994)
[10] Gordon A., Ford R., Chemist's Handbook [Russian Translation], (1976)

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