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

Kód výsledku v IS VaVaI

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Výsledek na webu

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DOI - Digital Object Identifier

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Jazyk výsledku

angličtina

Název v původním jazyce

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

Popis výsledku v původním jazyce

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.

Název v anglickém jazyce

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

Popis výsledku anglicky

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.

Druh

O - Ostatní výsledky

CEP obor

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OECD FORD obor

10401 - Organic chemistry

Projekt

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Návaznosti

S - Specificky vyzkum na vysokych skolach

Rok uplatnění

2019

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů