reactions of 1-aryl-2-bromo-3,4,4-trichlorobut-3-en-1-ones with some nucleophilic reagents文档.pdf

ISSN 1070-4280, Russian Journal of Organic Chemistry, 2007, Vol. 43, No. 11, pp. 1622–1627. © Pleiades Publishing, Ltd., 2007. Original Russian Text © V.I. Potkin, S.K. Petkevich, P.V. Kurman, 2007, published in Zhurnal Organicheskoi Khimii, 2007, Vol. 43, No. 11, pp. 1626–1632. Reactions of 1-Aryl-2-bromo-3,4,4-trichlorobut-3-en-1-ones with Some Nucleophilic Reagents V. I. Potkin, S. K. Petkevich, and P. V. Kurman Institute of Physical Organic Chemistry, National Academy of Sciences of Belarus, ul. Surganova 13, Minsk, 220072 Belarus e-mail: potkin@ifoch.bas-net.by Received February 2, 2007 Abstract—Reactions of 2-bromo-1-phenyl- and 2-bromo-1-(4-methylphenyl)-3,4,4-trichlorobut-3-en-1-ones with morpholine and diethylamine are accompanied by prototropic allylic rearrangement, leading to 3-amino-1- aryl-2-bromo-4,4-dichlorobut-2-en-1-ones as mixtures of E and Z isomers. The title compounds react with hydrazine, hydroxylamine, and thiourea to give the corresponding 5-aroyl-4-methoxypyrazoles, 3-aryl-5- hydroxyiminomethyl-4-methoxyisoxazoles, and 2-amino-4-aryl-5-trichlorovinylthiazoles. DOI: 10.1134/S1070428007110061 Halogen-substituted ketones are widely used in the ment of the initial ketones into isomeric conjugated synthesis of various practically important products bromochlorovinyl ketones Ib and IIb, followed by [1–4]. Chlorovinyl ketones attract specific interest due replacement of the chlorine atom in position 3 by to their high reactivity arising from mutual effect of amino group. As a result, the corresponding 3-amino- the conjugated carbonyl and chl