Novel Synthetic Approach to Benzo[e]pyrrolo[1,2-a][1,4]diazepine-5,11-dione Derivatives

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F70883521%3A28110%2F19%3A63523398" target="_blank" >RIV/70883521:28110/19:63523398 - isvavai.cz</a>
Result on the web
—
DOI - Digital Object Identifier
—

Result language
angličtina
Original language name
Novel Synthetic Approach to Benzo[e]pyrrolo[1,2-a][1,4]diazepine-5,11-dione Derivatives
Original language description
Numerous title compounds attract attention due to their biological effects, e.g. antibacterial activity against Gram positive as well as Gram negative bacteria, and antimycobacterial activity. So far, the syntheses of the title compounds described in the literature have been based on the reaction of isatoic anhydride with proline or its methyl ester, and on cyclisation of 1-(2-aminobenzoyl)pyrrolidine-2-carboxylates or N-(2-azidobenzoyl)proline methyl esters. We developed an approach to the title compounds 3, which starts from 3-aminoquinoline-2,4-diones 1. By the recently described reaction, the amine 1 is converted to 3,4-dihydro-1H-benzo[e][1,4]diazepine-2,5-dione derivative 2, in which the sunstiruent on the nitrogen atom in position 3 (R3) is 3-hydroxypropyl or propargyl. Compounds 2 with R3 = 3-hydroxypropyl are converted to those with R3 = 3-chloropropyl, which undergo base mediated cyclization to give compounds 3 with saturated five-membered ring. Compounds 2, in which R3 is propargyl group, are converted in the presence of a base to compounds 3 with double bond between C2 and C3.
Czech name
—
Czech description
—

Publication year
2019
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Similar results(10)