Author: Tillaeva, Adolat Farxodovna; Eshchanov, Xushnudbek Odilbekovich; Kuryazov, Rustamxon Shonazarovich; Taxirov, Yuldash Radjabovich; Dushamov, Dilshod Azadovich

Annotation: The reaction of 6-bromoquinazoline-2,4(1H,3H)-dione with chlorosulfonic acid gives 6-bromo-2,4-dioxo-1,2,3,4-tetrahydroquinozolin-8- sulfonyl chloride was shown to form. As a result of quantum chemical calculations, this situation is explained by the fact that sulfonyl chloride's total energy is lower than sulfoacid's. Also, under the influence of the positive mesomeric effect (+M) of the bromine atom, the sulfonyl chloride group should attack the 7th state of the molecule, but it has been proved both practically and theoretically that it goes to the 8th state. It was determined that 6-bromo-2,4-dioxo-1,2,3,4-tetrahydroquinozoline-8-sulfonic acid and its ester are formed from the chemical reaction of the product with water and alcohol.

Keywords: 6-bromoquinazoline-2,4(1H,3H)-dione, chlorosulfonic acid, 6-bromo-2,4-dioxo-1,2,3,4-tetrahydroquinazoline-8-sulfonyl chloride, nucleophilic substitution, 6-bromo-2,4-dioxo-1,2,3,4-tetrahydroquinozoline-8-sulfonic acid, 6-bromo-2,4-dioxo-1,2,3,4-tetrahydroquinozoline-8-sulfonic acid methyl ester, 6-bromo-2,4-dioxo-1,2,3,4-tetrahydroquinozolin-8-sulfonic acid ethyl ester, quantum chemical calculations, GAMESS calculation.

Pages in journal: 735 - 744