Preparation of 3-(pyridinyl)-2-cyclohexene-1-ones

Details Preparation of 3-(pyridinyl)-2-cyclohexene-1-ones Preparation of 3-(pyridinyl)-2-cyclohexene-1-ones

1978-01-19

1978-11-28

Randolph, John D.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D21346

Patent

active

041275837

ABSTRACT:
3-(4- OR 3-Pyridinyl)-2-cyclohexen-1-ones (I) and their oxime derivatives are useful in preparing (3-aminophenyl)pyridines, in turn, useful in preparing known antibacterial agents. Also shown is the preparation of I by starting with the reaction of methyl vinyl ketone with either 1-(pyridinyl)-1-(lower-tertiary-amino)-ethylene (II) or lower-alkyl 3-(pyridinyl)-3-oxopropanoate. Also shown is the process of converting I to its oxime, acylating the oxime and heating the acylated oxime under acidic conditions to produce N-(lower-acyl)-3-(pyridinyl)-aniline (VII), and hydrolyzing VII under aqueous alkaline conditions to produce the corresponding 3-(pyridinyl)aniline.

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Ross et al., J. Org. Chem., vol. 29, pp. 2341 to 2350 (1964).
Compagnon et al., Bull. Soc. Chim. France, 1968, pp. 4132 to 4136.
Mohrle et al., Arch. Pharmaz. vol. 307, pp. 550 to 560 (1974).

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