One Pot Tandem P-Michael Addition/SN2/Intramolecular Wittig Reaction of aza-o-Quinone Methides: Construction of 2,3-Disubstituted Dihydroquinoline Derivatives DOI

Y. C. Liu,

Hang Cheng,

Zhao‐Lin He

et al.

Chinese Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 44(7), P. 2241 - 2241

Published: Jan. 1, 2024

Language: Английский

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 DOI Open Access
Kai‐Kai Wang, Junwei Ye,

Jun Jia

et al.

Tetrahedron, Journal Year: 2023, Volume and Issue: 150, P. 133772 - 133772

Published: Dec. 1, 2023

Language: Английский

Citations

4
Synthesis of Functionalized Tetrahydroquinoline Containing Indole Scaffold via Chemoselective Annulation of Aza-ortho-quinone Methide Precursor DOI Creative Commons
Xiaoke Zhang,

Qianlu Xing,

Zhengxing Gou

et al.

ACS Omega, Journal Year: 2023, Volume and Issue: 8(25), P. 22352 - 22360

Published: June 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.

Language: Английский

Citations

2
Investigations on Superbase Mediated Reactivity of N‐Tosylhydrazones with Aza‐ortho‐Quinone Methide Precursors DOI

P Rahul,

T. K. Arunkumar,

Seena Sebastian

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(18)

Published: March 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.

Language: Английский

Citations

0
One Pot Tandem P-Michael Addition/SN2/Intramolecular Wittig Reaction of aza-o-Quinone Methides: Construction of 2,3-Disubstituted Dihydroquinoline Derivatives DOI

Y. C. Liu,

Hang Cheng,

Zhao‐Lin He

et al.

Chinese Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 44(7), P. 2241 - 2241

Published: Jan. 1, 2024

Language: Английский

Citations

0