Patent GB-913934-A (GB)
Title: Condensed heterocyclic compounds
IPC: C07D487/04
Filed: 1959-03-02
Abstract: The invention comprises compounds of the formula <FORM:0913934/IV (b)/1> or <FORM:0913934/IV (b)/2> where Q is a C2-18 divalent hydrocarbon group which (a) is free of non-aromatic unsaturation, (b) is attached to each nitrogen atom through a carbon atom which is itself attached to not more than two other carbon atoms, and (c) contains a chain of two or three carbon atoms between the two nitrogen atoms; R2 is hydrogen or C1-4 alkyl; and R1, R3, R4 and R5 are hydrocarbon groups free of non-aromatic unsaturation, or R3, R4 or R5 may be hydrogen, or one of the pairs R1R2, R1R3, R2R3 and R3R4 or both the pairs R1R2 and R3R4 may be joined together to form a cyclopentyl or cyclohexyl group which may contain one or more alkyl substituents and/or a methylene bridge which together contribute a total of not more than four additional carbon atoms; acid addition salts thereof; and their preparation by reacting one mole of a cyanoketone <FORM:0913934/IV (b)/3> with one mole of a diamine H2NQNH2, e.g. in the presence of an inert solvent that forms an azeotrope with water, the water formed in the reaction being preferably removed azeotropically during the reaction.  The second formula above is the tautomeric form of the first in the case when R1 is a group R5CH2-.  Examples prepare (1) a mixture (1 : 19) of 2,3-dihydro - 5,7,7 - trimethyl-(7H)-imidazo[1,2-a] pyrrole and 2,3,5,6-tetrahydro-5-methylene-7,7-dimethyl-(7H)-imidazo[1, 2-a]pyrrole; (2) a mixture of 2,3 - dihydro-2,5,7,7-tetramethyl-(7H)-imidazo[1,2-a]pyrrole and 2,3,5,6-tetrahydro - 5 - methylene - 2,7,7 - trimethyl-(7H)-imidazo[1,2-a]pyrrole; (3) a mixture of 6,8,8-trimethyl - 2,3,4,8 - tetrahydropyrrolo[1,2 - a] pyrimidine and 6 - methylene - 8,8 - dimethyl-2,3,4,6,7,8 - hexahydropyrrolo[1,2 - a]pyrimidine; and (4) a mixture of 1,3,3-trimethyl-(3H)-pyrrolo[1,2-a]benzimidazole and 1-methylene-3,3 - dimethyl - 1,2-dihydro-(3H)-pyrrolo[1,2-a] benzimidazole and 1-methylene-3,3-dimethyl-1,2 - dihydro-(3H)-pyrrolo[1,2-a]benzimidazole; this is easily hydrolysed during isolation and crystallisation to give 1-(2-aminophenyl)-2,4,4-trimethyl - 2 - pyrrolin-5-one.  Other products, cyanoketones and diamines, and suitable R groups are listed.  These compounds are pesticides (see Group VI). Specification 913,933 also is referred to.ALSO:Pesticidal compositions, e.g. fungicides, comprise a diluent and a compound of formula <FORM:0913934/VI/1> or an acid addition salt thereof, where Q is a C2-18 divalent hydrocarbon group which (a) is free of non-aromatic unsaturation, (b) is attached to each nitrogen atom through a carbon atom which is itself attached to not more than two other carbon atoms, and (c) contains a chain of two or three carbon atoms between the two nitrogen atoms; R2 is hydrogen or C1-4 alkyl; and R1, R3, R4 and R5 are hydrocarbon groups free of non-aromatic unsaturation, or R3, R4 or R5 may be hydrogen, or one of the pairs R1, R2; R1, R3; R2, R3 and R3, R4 or both the pairs R1, R2 and R3, R4 may be joined together to form a cyclopentyl or cyclohexyl group which may contain one or more alkyl substituents and/or a methylene bridge which together contribute a total of not more than four additional carbon atoms (see Group IV (b)).  The compositions may be powders, solutions, emulsions or dispersions. Many acid addition salts are specified.  The compounds of the above formul  are also said to be useful as hypotensive agents. Specification 913,933 also is referred to.