Rearrangement of some chlorosubstituted 3-amino-3,4-dihydro-1-hydroxycarbostyrils in hydrogen halide acids

Autor:	James A. Rabon, Larry L. Maples, Larry D. Gage, Alvie L. Davis, Stephen F. Kelley, Tommy J. McCord
Rok vydání:	1976
Předmět:	Chemistry Organic Chemistry Halogenation Halide Chloride Medicinal chemistry Ion Hydrogen halide chemistry.chemical_compound Nucleophile Bromide medicine Organic chemistry medicine.drug
Zdroj:	Journal of Heterocyclic Chemistry. 13:1091-1094
ISSN:	1943-5193 0022-152X
DOI:	10.1002/jhet.5570130531
Popis:	The general conditions and results of rearrangement studies of the 5-, 6-, 7-, and 8-chloro-substituted 3-amino-3,4-dihydro-1-hydroxycarbostyrils in concentrated hydrochloric and hydro-bromic acids to the corresponding dihalosubstituted 3-amino-3,4-dihydrocarbostyrils have been described. The 5-, 7- and 8-chlorocarbostyrilhydroxamic acids undergo nucleophilic displacement by either chloride or bromide ion preferentially at the 6-position to form the respective 5,6-, 6,7- and 6,8-dihalolactams. However, with the 3-amino-6-chloro-3,4-dihydro-1-hydroxycarbo-styril where the 6-position is blocked, nucleophilic displacement by halide ions occurs at the 8-position to afford the 6,8-dihalolactams. The 6,8-dichloro- and 6,8-dibromolactams were also prepared by alternative halogenation procedures for purposes of comparison with the rearrangement products.
Databáze:	OpenAIRE
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