Cyanocarboxamidines and quinazoline process

Claim 2

A compound selected from the group consisting of cyanocarboxamidines having formula II ##STR28## wherein n is equal to 2 to 3, A is hydrogen or lower alkyl of 1 to 4 carbon atoms inclusive; B and C are independently selected from the group consisting of lower alkoxy of 1 to 4 carbon atoms inclusive, R 1 is selected from the group consisting of lower alkyl of from 1 to 6 carbon atoms inclusive, R 2 C═O in which R 2 is cycloalkenyl, cycloalkyl, methylcycloalkyl in which cycloalkyl and cycloalkenyl are from 3 to 8 carbon atoms inclusive, hydroxyalkoxy of from 2 to 6 carbon atoms inclusive or phenyl, and ZC═O in which Z is a heterocyclic radical selected from the group consisting of ##STR29## in which X is either oxygen or sulfur, R a is lower alkyl of 1 to 6 carbon atoms inclusive, R b is selected from the group consisting of hydrogen, amino, lower alkyl of 1 to 4 carbon atoms inclusive and NHCO 2 R c in which R c is lower alkyl of 1 to 4 carbon atoms inclusive, R d and R e are independently selected from the group consisting of hydrogen, lower alkyl of 1 to 6 carbon atoms inclusive, lower alkoxy of 1 to 6 carbon atoms inclusive, and lower alkylthio of 1 to 6 carbon atoms inclusive.

Claim 3

The compound of formula II which is 4-methyl-piperazine-1-[N-cyano-N'-(3,4-dimethoxyphenyl)]carboxamidine.

Claim 4

The compound of formula II which is 4-methyl-piperazine-1-[N-cyano-N'-(3,4-dimethoxyphenyl)]carboxamidine.

Claim 5

The compound of formula II which is 4-(2-furoyl)piperazine-1-[N-cyano-N'-(3,4-dimethoxyphenyl)]carboxamidine.

Claim 6

The compound of formula II which is 4-(2-furoyl)piperazine-1-[N-cyano-N'-(3,4-dimethoxyphenyl)]carboxamidine.

Claim 7

The compound of formula II which is 4-(5-methylthio-1,3,4-oxadiazole-2-carbonyl)piperazine-1-[N-cyano-N'-(3,4-dimethoxyphenyl)]carboxamidine.

Claim 8

The compound of formula II which is 4-(5-methylthio-1,3,4-oxadiazole-2-carbonyl)piperazine-1-[N-cyano-N'-(3,4-dimethoxyphenyl)]carboxamidine.

Claim 9

A process for preparing a quinazoline compound of formula I ##STR30## wherein n is equal to 2 or 3; A is hydrogen or lower alkoxy of 1 to 4 carbon atoms inclusive; B and C are independently selected from the group consisting of lower alkoxy of 1 to 4 carbon atoms inclusive; R 1 is selected from the group consisting of lower alkyl of from 1 to 6 carbon atoms inclusive; R 2 CO in which R 2 is cycloalkenyl, cycloalkyl, methylcycloalkyl in which cycloalkyl and cycloalkenyl are from 3 to 8 carbon atoms inclusive; hydroxyalkoxy from 2 to 6 carbon atoms inclusive or phenyl; and ZC═O in which Z is a heterocyclic radical selected from the group consisting of ##STR31## in which X is either oxygen or sulfur, R a is lower alkyl of 1 to 6 carbon atoms inclusive, R b is selected from the group consisting of hydrogen, amino, lower alkyl of 1 to 4 carbon atoms inclusive and NHCO 2 R c in which R c is lower alkyl of 1 to 4 carbon atoms inclusive, R d and R e are independently selected from the group consisting of hydrogen, lower alkyl of 1 to 6 carbon atoms inclusive, lower alkoxy of 1 to 6 carbon atoms inclusive, and lower alkylthio of 1 to 6 carbon atoms inclusive which comprises cyclizing a cyanocarboxamidine of formula II ##STR32## wherein the symbols "A, B, C, n and R 1 " are as recited above.

Claim 10

A process for preparing a quinazoline compound of formula I ##STR30## wherein n is equal to 2 or 3; A is hydrogen or lower alkoxy of 1 to 4 carbon atoms inclusive; B and C are independently selected from the group consisting of lower alkoxy of 1 to 4 carbon atoms inclusive; R 1 is selected from the group consisting of lower alkyl of from 1 to 6 carbon atoms inclusive; R 2 CO in which R 2 is cycloalkenyl, cycloalkyl, methylcycloalkyl in which cycloalkyl and cycloalkenyl are from 3 to 8 carbon atoms inclusive; hydroxyalkoxy from 2 to 6 carbon atoms inclusive or phenyl; and ZC═O in which Z is a heterocyclic radical selected from the group consisting of ##STR31## in which X is either oxygen or sulfur, R a is lower alkyl of 1 to 6 carbon atoms inclusive, R b is selected from the group consisting of hydrogen, amino, lower alkyl of 1 to 4 carbon atoms inclusive and NHCO 2 R c in which R c is lower alkyl of 1 to 4 carbon atoms inclusive, R d and R e are independently selected from the group consisting of hydrogen, lower alkyl of 1 to 6 carbon atoms inclusive, lower alkoxy of 1 to 6 carbon atoms inclusive, and lower alkylthio of 1 to 6 carbon atoms inclusive which comprises cyclizing a cyanocarboxamidine of formula II ##STR32## wherein the symbols "A, B, C, n and R 1 " are as recited above.

Claim 11

The process of claim 5 wherein the compound of formula II employed is 4-methylpiperazine-1-[N-cyano-N'-(3,4-dimethoxyphenyl)]carboxamidine.

Claim 12

The process of claim 5 wherein the compound of formula II employed is 4-(2-furoyl)piperazine-1-[N-cyano-N'-(3,4-dimethoxyphenyl)]carboxamidine.

Claim 13

The process of claim 5 wherein the compound of formula II employed is 4-(5-methylthio-1,3,4-oxadiazole-2-carbonyl)piperazine-1-[N-cyano-N'-(3,4-dimethoxyphenyl)]carboxamidine.

Claim 14

The process of claim 5 wherein the cyclization process is carried out by treating the compound of formula II with phosphorus trichloride or phosphorus pentachloride in a solvent amount of phosphorus oxychloride.

Claim 15

The process of claim 5 wherein the cyclization process is carried out by treating the compound of formula II with phosphorus tribromide or phosphorus pentabromide in a solvent amount of phosphorus oxybromide.

Claim 16

The process of claim 5 wherein the cyclization process is carried out by treating the compound of formula II with aqueous hydrochloric acid.

Claim 17

The process of claim 5 wherein the cyclization process is carried out by treating the compound of formula II with hydrogen chloride in phosphorus oxychloride.

Claim 18

The process of claim 5 wherein the cyclization process is carried out by treating the compound of formula II with a Lewis acid catalyst.

Claim 19

The process of claim 5 wherein the cyclization process is carried out at a temperature of 25°-125°.

Claim 20

The process of claim 5 wherein the cyclization process is carried out at a temperature of 70°-100°.

Claim 21

The process of claim 5 wherein the cyclization process is carried out for a period at 1 to 3 hours at a temperature in the range of 70°-100°.

Claim 22

A process for the preparation of a quinazoline of formula Ia ##STR33## which comprises cyclizing a cyanocarboxamidine having formula IIa ##STR34##

Claim 23

A process for the preparation of a quinazoline of formula Ia ##STR33## which comprises cyclizing a cyanocarboxamidine having formula IIa ##STR34##

Claim 24

A process for the preparation of a quinazoline of formula Ib ##STR35## which comprises cyclizing a cyanocarboxamidine having formula IIb ##STR36##

Claim 25

A process for the preparation of a quinazoline of formula Ib ##STR35## which comprises cyclizing a cyanocarboxamidine having formula IIb ##STR36##

Claim 26

A process for the preparation of a quinazoline of formula Ic ##STR37## which comprises cyclizing a cyanocarboxamidine having formula IIc ##STR38##

Claim 27

A process for the preparation of a quinazoline of formula Ic ##STR37## which comprises cyclizing a cyanocarboxamidine having formula IIc ##STR38##

Claim 28

A process for the preparation of a quinazoline of formula Id ##STR39## which comprises cyclizing a cyanocarboxamidine having formula IId ##STR40##

Claim 29

A process for the preparation of a quinazoline of formula Id ##STR39## which comprises cyclizing a cyanocarboxamidine having formula IId ##STR40##