6,7-dihydrobenzimidazo[1,2-c]quinazolin-6-one carboxylic acids, their esters, and methods of synthesis thereof
AssigneeCrysoptix KK
InventorsTatyana Doutova, Pavel I. Lazarev, Elena N. Sidorenko, Valery S. Kuzmin
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Abstract
The present invention relates to a 6,7-dihydrobenzimidazo[1,2-c]quinazolin-6-one carboxylic acid and its esters of the general structural formula (I), and provides a method for their synthesis (I) where R and each R′ are selected independently from the list comprising —H—CH3, —C2H5, —C3H7, -iso-C3H7, —CH2CH2CH2CH3, —CH(CH3)CH2CH3, —CH2CH(CH3)CH3 and —C(CH3)3; n is 1, 2, 3 or 4; Y is a substituent selected from the list comprising —CH3, —C2H5, —NO2, —Cl, —Br, —F, —CF3, —CN, —OH, —OCH3, —OC2H5, —OCOCH3, —OCN, —SCN, —NH2, —NHCOCH3; and z is 0, 1, 2, 3 or 4.
Claims55
A 6,7-dihydrobenzimidazo[1,2-c]quinazoline-6-one carboxylic acid and its esters of the general structural formula
- where R and each R′ are selected independently from the list comprising —H, —CH3, —C2H5, —C3H7, -iso-C3H7, —CH2CH2CH2CH3, —CH(CH3)CH2CH3, —CH2CH(CH3)CH3 and —C(CH3)3,
- n is 1, 2, 3 or 4,
- Y is a substituent selected independently from the list comprising —CH3, —C2H5, —NO2, —Cl, —Br, —F, —CF3, —CN, —OH, —OCH3, —OC2H5, —OCOCH3, —OCN, —SCN, —NH2, —NHCOCH3, and
- z is 0, 1, 2, 3 or 4.
A method for the synthesis of a 6,7-dihydrobenzimidazo[1,2-c]quinazolin-6-one carboxylic acid and its esters of the general structural formula
- where R and each R′ are selected independently from the list comprising —H,—CH3, C2H5, C3H 7, -iso-C3H7, —CH2CH2CH2CH3, —CH(CH3)CH2CH3, —CH2CH(CH3)CH3 and —C(CH3)3;
- n is 1, 2, 3 or 4;
- Y is a substituent selected from the list comprising —CH3, —C2H5, —NO2, —Cl, —Br, —F, —CF3, —CN, —OH, —OCH3, —OC2H5, —OCOCH3, —OCN, —SCN, —NH2, —NHCOCH3;
- and z is 0, 1, 2, 3 or 4,
- which method comprises the step of reacting in the presence of an oxidant a component of the formula (II):
- where n′ is 0, 1 or 2, z′ is 0, 1 or 2;
- with a component of the formula (III):
- where n″ is 0, 1 or 2, z″ is 0, 1 or 2, and n′+n″≧1.
A method for the synthesis of a 6,7-dihydrobenzimidazo[1,2-c]quinazolin-6-one carboxylic acid and its esters of the general structural formula
- where R and each R′ are selected independently from the list comprising —H,—CH3, —C2H5, —C3H7, -iso-C3H7, —CH2CH2CH2CH3, —CH(CH3)CH2CH3, —CH2CH(CH3)CH3 and —C(CH3)3;
- n is 1, 2, 3 or 4;
- Y is a substituent selected from the list comprising —CH3, —C2H5, —NO2, —Cl, —Br, —F, —CF3, —CN, —OH, —OCH3, -0C2H5, —OCOCH3, —OCN, —SCN, —NH2, —NHCOCH3;
- and z is 0, 1, 2, 3 or 4,
- which method comprises the step of:
- (a) preparing a mixture comprising a solvent;
- a component selected from the group including isatin and its derivatives of the general structural formula (II),
- where n′ is 0, 1 or 2, and z′ is 0, 1 or 2;
- and a component selected from the group consisting of o-phenylenediamine and its derivatives of the general structural formula (III):
- where n″ is 0, 1 or 2, z″ is 0, 1 or 2, and n′+n″≧1;
- (b) treating said mixture with an oxidant;
- (c) allowing the reaction to progress;
- and
- (d) isolating the 6,7-dihydrobenzimidazo[1,2-c]quinazolin-6-one carboxylic acid and its esters from the reaction mass.
A method for the synthesis of a 6,7-dihydrobenzimidazo[1,2-c]quinazolin-6-one carboxylic acid and its esters of the general structural formula
- where R and each R′ is selected independently from the list comprising —H,—CH3, —C2H5, —C3H7, -iso-C3H7, —CH2CH2CH2CH3, —CH(CH3)CH2CH3, —CH2CH(CH3)CH3 and —C(CH3)3, n is 1, 2, 3 or 4, Y is a substituent selected from the list comprising —CH3, —C2H5, —NO2, —Cl, —Br, —F, —CF3, —CN, —OH, —OCH3, -002H5, —OCOCH3, —OCN, —SCN, —NH2, —NHCOCH3, and z is 0, 1, 2, 3 or 4,
- which comprises the following steps:
- (a) preparing a mixture consisting of a solvent;
- hydrochloric acid;
- a component selected from the group including isatin and its derivatives of the general structural formula (II),
- where n′ is 0, 1 or 2, and z′ is 0, 1 or 2;
- and a component selected from the group consisting of o-phenylenediamine and its derivatives of the general structural formula (III),
- where n″ is 0, 1 or 2, z″ is 0, 1 or 2, and n′+n″≧1;
- (b) treating said mixture with an oxidant selected from the group of inorganic and organic peroxides at a reaction temperature not higher than the temperature of side reactions;
- (c) stirring the obtained reaction mass at the reaction temperature until the reaction is completed;
- and
- (d) isolating the compound from the reaction mass.
Dependencies are inferred from the claim text.