N-Heterocyclic carbene-catalyzed annulation of cyclic β-enamino esters with enals: access to functionalized indolo[2,3-a]quinolizidines

Hu, Sheng-Zhi; Wang, Bingyang; Tang, Weifang; Fang, Mengyuan; Lü, Tao; Du, Ding

doi:10.1039/c5ob00176e

Cited by 34 publications

(11 citation statements)

References 88 publications

(26 reference statements)

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“…In 2013 and 2015, Lu and co-workers completed NHCcatalyzed cycloaddition leading to the preparation of Scheme 8 The enantioselective synthesis of spirocyclic oxindole seven-membered-3-lactams. 31 respectively. In the presence of NHC C2 generated from the triazolium salt and base, the desired products were obtained in moderate to good yields (Scheme 10).…”

Section: Applications In the Synthesis Of Indole Derivativesmentioning

confidence: 98%

“…In 2013 and 2015, Lu and co-workers completed NHC-catalyzed cycloaddition leading to the preparation of functionalized 3,4-dihydropyrano[3,2- b ] indol-2-ones 43 (ref. 30 ) and indolo[2,3- a ] quinolizidines 44, 31 respectively. In the presence of NHC C2 generated from the triazolium salt and base, the desired products were obtained in moderate to good yields ( Scheme 10 ).…”

Section: Applications Of Nhcs In the Construction Of Biologically Act...mentioning

confidence: 99%

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Recent advances of N-heterocyclic carbenes in the applications of constructing carbo- and heterocyclic frameworks with potential biological activity

Chen

Deng

et al. 2021

RSC Adv.

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Section: Applications In the Synthesis Of Indole Derivativesmentioning

confidence: 98%

Section: Applications Of Nhcs In the Construction Of Biologically Act...mentioning

confidence: 99%

Recent advances of N-heterocyclic carbenes in the applications of constructing carbo- and heterocyclic frameworks with potential biological activity

Chen

Deng

et al. 2021

RSC Adv.

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“…The functionalized indolo[2,3‐ a ]quinolizidines 81 heterocycle was synthesized by Du and co‐workers by NHC‐catalyzed oxidative annulation of cyclic β ‐enamino esters 79 with enals 80 (Scheme 21). [48] …”

Section: Figurementioning

confidence: 99%

“…[47] The functionalized indolo[2,3-a] quinolizidines 81 heterocycle was synthesized by Du and co-workers by NHC-catalyzed oxidative annulation of cyclic βenamino esters 79 with enals 80 (Scheme 21). [48] Postulated reaction mechanism, as shown in scheme 22, for this annulation proceeds through Breslow…”

Section: Indolo[23-a]quinolizidinesmentioning

confidence: 99%

Recent Advances in N‐Heterocyclic Carbene Catalyzed Oxidative Cyclization for the Formation of Heterocycles

2021

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Oxidative N‐heterocyclic carbene catalyst mediated cyclization proved to be an efficient strategy for the construction of various N‐ and O‐ heterocycles. Among several metal‐free methods available for the construction of heterocyclic compounds, oxidative NHC catalysis proved to be an elegant and efficient strategy as several enantioenriched compounds with excellent enantioselectivities can be synthesized in good yields. The most common method of the generation of these heterocycles proceeds via the commonly encountered intermediate in oxidative NHC catalysis (i. e.) acyl azolium intermediate. This intermediate proves to be the active species as it can undergo reaction with suitable substrates leading to the formation of numerous N‐ and O‐ heterocycles. Herein, recent reports on different strategies that enable formal [2+2], [3+2], [3+3], [4+2] or [4+3] annulations between the incoming substrates and acyl azolium species or other active intermediates which can add to suitable substrate leading to various heterocycles were summarized.

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“…Fused heterocylic compounds have long been known for their significant applications in pharmaceutical and biomedical industries . They possess significant roles to serve as bioactive lead molecules and molecular recognition events . They are present in numerous natural products agrochemicals and pharmaceuticals .…”

Section: Introductionmentioning

confidence: 99%

Investigation on Photophysical, Solvatochromism and Biological Significance of Substituted 2H‐Indazole Derivatives

2020

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The electronic properties of substituted 2H-indazoles were investigated for their photophysical behavior under isolated conditions and in solvent environment, both computationally and experimentally. DFT calculations with CAMÀ B3LYP functional and 6-311 + + G** basis set were performed in the ground and excited states. The effect of solvents on the low and high energy electronic states was studied by following the steady state absorption and fluorescence excitation and emission spectra. Solvatochromic interactions including general and specific solvent effects are reported along with the results of Lippert and E T (30) plots. The biological significance of these 2H-indazole derivatives was also investigated through docking studies. The interactions of 2H-indazole derivatives with the active site of subdomain II of human casein kinase (C2 K) alpha are reported.

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N-Heterocyclic carbene-catalyzed annulation of cyclic β-enamino esters with enals: access to functionalized indolo[2,3-a]quinolizidines

Cited by 34 publications

References 88 publications

Recent advances of N-heterocyclic carbenes in the applications of constructing carbo- and heterocyclic frameworks with potential biological activity

Recent advances of N-heterocyclic carbenes in the applications of constructing carbo- and heterocyclic frameworks with potential biological activity

Recent Advances in N‐Heterocyclic Carbene Catalyzed Oxidative Cyclization for the Formation of Heterocycles

Investigation on Photophysical, Solvatochromism and Biological Significance of Substituted 2H‐Indazole Derivatives

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