2001
DOI: 10.1021/jo0105540
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Synthesis of Isoquinolines and Pyridines by the Palladium-Catalyzed Iminoannulation of Internal Alkynes

Abstract: A wide variety of substituted isoquinoline, tetrahydroisoquinoline, 5,6-dihydrobenz[f]isoquinoline, pyrindine, and pyridine heterocycles have been prepared in good to excellent yields via annulation of internal acetylenes with the tert-butylimines of o-iodobenzaldehydes and 3-halo-2-alkenals in the presence of a palladium catalyst. The best results are obtained by employing 5 mol % of Pd(OAc)(2), an excess of the alkyne, 1 equiv of Na(2)CO(3) as a base, and 10 mol % of PPh(3) in DMF as the solvent. This annula… Show more

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Cited by 190 publications
(69 citation statements)
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“…It is also imperative to develop routes to highly-substituted isoquinolines to fully explore this chemical space, for example, for potential pharmaceutical targets. While recent synthetic efforts have greatly expanded the diversity of isoquinoline motifs available (16)(17)(18)(19)(20)(21)(22)(23)(24)(25)(26)(27)(28)(29), new routes to isoquinolines are still highly desirable, particularly ones with the ability to directly access the isoquinoline moiety in a range of oxidation levels and which do not require highly-specialized starting materials.…”
mentioning
confidence: 99%
“…It is also imperative to develop routes to highly-substituted isoquinolines to fully explore this chemical space, for example, for potential pharmaceutical targets. While recent synthetic efforts have greatly expanded the diversity of isoquinoline motifs available (16)(17)(18)(19)(20)(21)(22)(23)(24)(25)(26)(27)(28)(29), new routes to isoquinolines are still highly desirable, particularly ones with the ability to directly access the isoquinoline moiety in a range of oxidation levels and which do not require highly-specialized starting materials.…”
mentioning
confidence: 99%
“…In this context, Heck and co‐workers reported the formation of isoquinolinium salts from the reaction of cyclopalladated benzaldimines and alkynes,3 but they did not succeed in making the reaction catalytic. Later, Larock and co‐workers,4ab and our group4c independently reported a palladium‐ and nickel‐catalyzed synthesis of isoquinoline derivatives from N ‐ tert ‐butyl o ‐halobenzaldimines and alkynes. Recently, Fagnou et al.…”
Section: Results Of Rhodium‐catalyzed Ch Activation and Annulation Omentioning
confidence: 99%
“…This process occurred through the formyl intermediate 180, which then cyclizes and dehydrogenates to give 178 (Scheme 17.110) [308]. 17 [309,310]. When a relatively unhindered diyne and enyne, or an electron-rich imine, are employed mixtures of stereoisomers are obtained with high selectivity.…”
Section: Condensation Reaction-based Methodsmentioning
confidence: 99%