Patent GB-1087582-A (GB)
Title: Improvements in or relating to cycloalkenes and the manufacture thereof
IPC: C07C35/52
Filed: 1964-12-07
Abstract: Novel compounds of general formula <FORM:1087582/C4-C5/1> wherein R1, R2 and R3 are H, (C1- 8) alkyl or (C2- 8) alkenyl but all may not be H simultaneously, and n is 1 or 2, are prepared either by dehydration of an alkanol of formula <FORM:1087582/C4-C5/2> or by reaction of a ketone of formula <FORM:1087582/C4-C5/3> with a Grignard reagent of formula <FORM:1087582/C4-C5/4>ALSO:Novel compounds of general formula <FORM:1087582/C2/1> wherein R1 is H (C1- 8) alkyl, -CF3 (C2- 8) alkenyl, (C2- 8) alkenyloxy, halogen, (C1- 8) alkylmercapto, -NR4R5 or -A-N.R4R5 where R4 and R5 are (C1- 8) alkyl or -NR4R5 is a 5 to 7 membered saturated heterocyclic radical, and A is (C1-C6) alkylene; R2 is H or at least one substituent selected from (C1- 8) alkyl, -CF3 (C2- 8) alkenyl, (C2- 8 alkenyloxy, halogen, (C1- 8) alkylmercapto or -NR4R5; R3 is H or at least one substituent selected from -OH, -CF3, (C1- 8) alkyl, (C2- 8) alkenyl, (C1- 8) alkoxy, (C2- 8) alkenyloxy, halogen, (C1- 8) alkylmercapto or -NR4R5, but R1, R2 and R3 may not all be H simultaneously, and n is 1 or 2, and acid addition and quaternary salts of the basic compounds, are prepared either by dehydration of a compound of formula <FORM:1087582/C2/2> or by reaction of a compound of formula <FORM:1087582/C2/3> with a Grignard reagent of formula <FORM:1087582/C2/4> The ketones of the second general formula above are prepared by cyclization of either of the acids of formulae  <FORM:1087582/C2/5> <FORM:1087582/C2/6> The carboxylic acids of the last two formulae above are prepared either by reaction of an optionally substituted benzyl halide and an optionally substituted phenyl acetic acid or by reduction of a compound of formula  <FORM:1087582/C2/7> The keto-acids of the last formula above are prepared by hydrolysis of the corresponding nitriles.  The keto-nitriles of general formula <FORM:1087582/C2/8> are prepared by reaction of hydrogen cyanide and a chalcone of formula <FORM:1087582/C2/9> which is prepared by condensation of the appropriate acetophenone and benzaldehyde.  Substituted halobenzenes Halogen C6H4AN R4 R5 are prepared by reduction of the corresponding amides which are prepared by reaction of the halo acid with HNR4R5. Pharmaceutical compositions in conventional forms for oral or parenteral administration comprise an above novel compound and a solid or liquid pharmaceutical carrier or excipient.ALSO:Pesticidal formulations for use against rodents and other small animals and birds comprise a bait and/or attractant and a compound of general formula <FORM:1087582/A5-A6/1> wherein R1 is H, -CF3, (C1-8) alkyl, (C2-8) alkenyl, (C2-8) alkenyloxy, halogen, (C1-8) alkylmercapto, -NR4 R5 or -A-NR4R5 where R4 and R5 are (C1-8) alkyl or -NR4R5 is a 5 to 7 membered saturated heterocyclic radical and A is (C1-C6) alkylene; R2 is H or at least one substituent selected from (C1-8) alkyl, -CF3, (C2-8) alkenyl, (C2-8) alkenyloxy, halogen, (C1-8) alkylmercapto or -NR4R5, R3 is H or at least one substituent selected from OH, CF3, (C1-8) alkyl, (C2-8) alkenyl, (C1-8) alkoxy, (C2-8) alkenyloxy, halogen, (C1-8) alkylmercapto, or -NR4R5, but R1, R2 and R3 may not all be H, and n is 1 or 2, and acid addition and quaternary salts of basic compounds thereof.