An unexpected one-pot synthesis of multi-substituted quinolines via a cascade reaction of Michael/Staudinger/aza-Wittig/aromatization of ortho-azido-β-nitro-styrenes with various carbonyl compounds

Yu, Zhi-Hua; Zheng, Hu‐Fei; Wang, Yuan; Tang, Zilong; Zhang, Aidong; Shi, De‐Qing

doi:10.1016/j.tet.2013.07.050

Cited by 25 publications

(7 citation statements)

References 63 publications

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“…Multi‐substituted quinolones can be prepared from a cascade reaction of ortho ‐azido‐nitrostyrenes with various carbonyl compounds . This method includes a cascade Michael/Staudinger/aza‐Wittig reaction/aromatization reaction.…”

Section: Reactions With Electrophilesmentioning

confidence: 99%

Recent Advances in Reactions of Azides

2017

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Azides are important intermediates in organic synthesis. They can function as precursors to form amines, amides, quinolones, pyridines, triazoles, amidines, indoles, and so on. Although there are some reviews about the applications of azides, few are concerned about their fundamental mechanisms. This review will focus on recent advances of azides based on three reactivity patterns, which may enlighten the further research.

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Section: Reactions With Electrophilesmentioning

confidence: 99%

Recent Advances in Reactions of Azides

2017

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“…These compounds are related to histone acetyltransferase (HAT) inhibitors [ 94 , 95 , 96 ]. Shi and co-workers reported the synthesis of 2,3-substituted quinolines 25 via a condensation/Michael/Staudinger/aza-Wittig/aromatization reaction ( Scheme 8 ) [ 97 ]. The ortho -Azido- β -nitro-styrenes 23 , synthesized by the condensation of 2-azidobenzaldehydes 1 and MeNO 2 , undergo the Michael addition with ketones 24 to form 26 , which then reacts with PPh 3 according to the Staudinger reaction to afford intermediates 27 .…”

Section: Resultsmentioning

confidence: 99%

2-Azidobenzaldehyde-Based [4+2] Annulation for the Synthesis of Quinoline Derivatives

Zhang,

Liu,

Qiu

et al. 2024

Molecules

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Quinoline is a privileged heterocyclic ring which can be found in many drug molecules and bioactive compounds. The development of synthetic methods for making quinoline derivatives continuously attracts the interest of organic and medicinal chemists. This paper highlights 2-azidobenzaldehyde-based [4+2] annulation for the synthesis of quinoline derivatives including fused and spiro-quinolines, quinoline-4-ols, 4-aminoquinolines, and related compounds.

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“…The IMBH adducts, being unstable, were oxidized to quinoline using DDQ in DCM. Quinoline framework is one of the most privileged skeletons and has attracted significant attention from synthetic chemists worldwide …”

Section: Resultsmentioning

confidence: 99%

Chemoselective and Highly Rate Accelerated Intramolecular Aza-Morita–Baylis–Hillman Reaction

Bharadwaj

2018

J. Org. Chem.

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Despite being a very useful C−C bond forming and highly applicative reaction, Morita−Baylis−Hillman (MBH) reaction has been limited by its excessive slow reaction rate, including its intramolecular version. In certain cases, reaction time may even go to weeks and months. A highly chemoselective and rate accelerated intramolecular MBH reaction of just 15 min has been developed. The product dihydroquinoline, being unstable, was converted to an important quinoline framework. In some cases IMBH adducts were isolable, thus confirming the reaction path. Control experiments toward mechanism investigation have been carried out. Use of sodium sulfide has emerged as a rate accelerating catalyst in DMF−EtOH solvent system. Reaction intermediate for IMBH pathway was isolated and characterized. Other aspects such as the application of IMBH adduct for Michael addition and amidation have also been carried out.

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An unexpected one-pot synthesis of multi-substituted quinolines via a cascade reaction of Michael/Staudinger/aza-Wittig/aromatization of ortho-azido-β-nitro-styrenes with various carbonyl compounds

Cited by 25 publications

References 63 publications

Recent Advances in Reactions of Azides

Recent Advances in Reactions of Azides

2-Azidobenzaldehyde-Based [4+2] Annulation for the Synthesis of Quinoline Derivatives

Chemoselective and Highly Rate Accelerated Intramolecular Aza-Morita–Baylis–Hillman Reaction

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