Exceedingly facile one-pot protocols to the synthesis of pyrimido annulated analogues of carbazolo condensed azepinones and their evaluation for analgesic activity

Abstract

Extremely simple protocols based on the reactivity of corresponding oxoketenedithioacetal (4), 2-(dimethylaminomethylene) ketone (5), β-oxoenolether (6) and α,β-unsaturated ketone (7) derivatives of 7-ethyl-3, 4-dihydroazepino[3,2-b]carbazol-2,5(1H,7H)-dione (3) have been developed to provide an easy access to their pyrimido annulated analogues (8-15) of medicinal interest. The key compound 3 from which, the synthesis proceeded has been realized in two steps from the commercial 3-amino-9-ethyl carbazole (1) on its reaction in the first step with ethyl succinyl chloride followed by cyclocondensation of the resulting ester 2 with PPA. The selected synthesized compounds were screened for in-vivo analgesic activity using acetic acid induced writhing model in mice. Among them, compound 13was found to be most active and found comparable to standard aspirin.

One-pot mediated synthesis of pyrimidine and quinazoline annulated derivatives of nitrogen containing five membered rings through their nitrile derivatives as antibacterial agents

“…The activated benzanilide (29) was now ready to couple with substituted nitrile 3, 8, 13, 19, 24. The synthesized nitrilium (30)(31)(32)(33)(34) undergo cyclocondensation with the π-electron system of benzene ring to yield the quinazoline nucleus in a single step 35-39 depicted in Scheme 4 and mechanism shown in Scheme 6. Scheme 5.…”

“…pyrimidine [19][20][21][22][23][24][25], quinazoline [26][27][28], in the chemical literature is undoubtedly a result of the diverse biological response that they elicit in combating a wide range of body ailments. Pyrimidine and quinazoline are considered as "privileged structures" in therapeutic chemistry because these nucleus display a vast range of biological activities [29][30][31][32][33][34].…”

Metal‐Catalyzed Approaches for the Construction of Azepinones

“…The diverse class of seven-membered heterocycles includes azepines, 1,2-diazepine, 1,3-diazepine, 1,4-diazepine, azepane, 1,2-diazepane, 1,3-diazepane, 1,4-diazepane, azepinone, thiazipine, benzazepine, benzazepane, 1,4benzodiazepine, benzoazepinedione, benzothiazipin and dibenzazepinone (Figure 1). [7] Azepinones correspond to a vital class of seven-member heterocycles that exists in many naturally occurring organic compounds, [8] bioactive molecules, [9] medicinally relevant compounds [10] and natural products. [11] Many alkaloids contain azepinone nuclei as the core structure units (Figure 2).…”