Synthesis of functionalized spiro[indanone-benzazepine] scaffolds via [4 + 3] annulation reaction of N-(o-chloromethyl)aryl amides with ninhydrin-derived Morita−Baylis−Hillman carbonates

Tetrahedron, Год журнала: 2023, Номер 150, С. 133772 - 133772

Опубликована: Дек. 1, 2023

Язык: Английский

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Synthesis of Functionalized Tetrahydroquinoline Containing Indole Scaffold via Chemoselective Annulation of Aza-ortho-quinone Methide Precursor

ACS Omega, Год журнала: 2023, Номер 8(25), С. 22352 - 22360

Опубликована: Июнь 13, 2023

The chemoselective annulation of aza-ortho-quinone methide generated by in situ o-chloromethyl sulfonamide has been achieved with bifunctional acyclic olefin. This efficient approach provides access to the diastereoselective synthesis functionalized tetrahydroquinoline derivatives containing indole scaffolds through inverse-electron-demand aza-Diels-Alder reaction under mild conditions excellent results (up 93% yield, > 20:1 dr). Moreover, this article realized cyclization α-halogeno hydrazone electron-deficient alkene affording tetrahydropyridazine derivatives, which had never reported.

Язык: Английский

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Investigations on Superbase Mediated Reactivity of N‐Tosylhydrazones with Aza‐ortho‐Quinone Methide Precursors

European Journal of Organic Chemistry, Год журнала: 2024, Номер 27(18)

Опубликована: Март 16, 2024

Abstract We have encountered a superbase‐mediated chemoselective reaction of N ‐tosylhydrazones with aza‐ ortho ‐quinone methide precursors. When tosylhydrazone was treated ‐aminobenzyl alcohol in super basic conditions (KOH+DMSO), we observed the formation 2‐substituted quinoline. The found to be general, and by this method, mono‐, di‐ tri‐substituted quinolines could made. prove experimentally theoretically that proceeded via an azine from decomposition ‐tosylhydrazones. Finally, ‐(2‐(chloromethyl)phenyl)‐4‐methylbenzenesulfonamide (aza‐ precursor) under afforded hydrazine substituted sulfonamides.

Язык: Английский

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One Pot Tandem P-Michael Addition/S_N2/Intramolecular Wittig Reaction of aza-o-Quinone Methides: Construction of 2,3-Disubstituted Dihydroquinoline Derivatives

Chinese Journal of Organic Chemistry, Год журнала: 2024, Номер 44(7), С. 2241 - 2241

Опубликована: Янв. 1, 2024

Язык: Английский

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