1,3-Dipolar cycloaddition reactions of 4,6-diazaphenanthrene 6-phenacylide

Chemistry and applications of benzonaphthyridines

“…Cycloadduct 15 constituted a main product in the cycloaddition of benzo[f] [1,7]naphthyridine to DMAD carried out at room temperature in benzene solution. …”

“…However, in the σ-adduct with benzonaphthyridine 28 the negative charge was localized chiefly on the vicinal nitrogen atom, which behaved as a strong nucleophilic center and underwent fast intramolecular substitution leading to the annelation product, the aziridine derivative, 6-benzenesulfonyl-aziridine [ [1,7]-naphthyridine-4,6-dioxide were also investigated. They proceeded in acordance with literature data for some electrophilic bicyclic azines such as quinoxalines 25 and quinoxaline-1-oxide.…”

“…Isomeric benzo[c] [1,5]-, benzo[h] [1,6]-and benzo[f] [1,7]naphthyridines 1 -3, the theme of our research, are interesting for their chemical reactivity, biological properties, and applications. They exhibit a wide spectrum of biological activity such as bactericidal, fungicidal, and cancerostatic.…”

Synthesis of pyrrolo[1,2-a]quinolines by formal 1,3-dipolar cycloaddition reactions of quinolinium salts

“…Almost all of the examples of dipolar cycloaddition reactions involving quinolinium salts that have been reported in the literature involve ketones as electron-withdrawing groups to stabilise the intermediate ylide [39–49]; for example, the ketone 1 is known to undergo reaction with alkenes 2 (Z = electron-withdrawing group) to give the tricyclic products 3 (Scheme 1) [41,49]. Similar examples with phenanthridinium and related ylides make use of ketones to stabilise the ylide [50–54]. The only exception (as far as we are aware) to the use of quinolinium ylides with ketones as stabilising groups are isolated reports with a carboxylic acid derivative, particular an ethyl ester group [55–59].…”

Nonlinear optical materials with pyridinium salt fragments

“…Only methods using pyridinium quaternary salts and related compounds will be reviewed here, since our own research is on azaaromatic quaternary salts [38,39]. Only methods using pyridinium quaternary salts and related compounds will be reviewed here, since our own research is on azaaromatic quaternary salts [38,39].…”