Diastereoselective Synthesis of C3‐Quaternary Indolenines Using α,β‐Unsaturated <i>N</i>‐Aryl Ketonitrones and Activated Alkynes

Huehls, C. Bryan; Hood, Tyler S.; Yang, Jiong

doi:10.1002/ange.201200860

Cited by 7 publications

(1 citation statement)

References 81 publications

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“…292 The reaction of α,β-unsaturated N-aryl ketonitrones with activated alkynes gives C3-quaternary inodolenines without transition metal catalysis via [5 + 2] cyclization (eq 136). 293 The reaction of nitrones with o-carboryne affords carboranefused seven-membered heterocycles via formal [5 + 2] cycloaddition. The [3 + 2] cycloaddition, N−O bond cleavage, oxygen migration, and rearomatization seems to be involved (eq 137).…”

Section: Reaction Of Nitrone-functionalized Terminal Alkynesmentioning

confidence: 99%

Synthesis and Transformations of Nitrones for Organic Synthesis

2019

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Nitrones are important compounds and are highly useful in many aspects. The first part describes the methods for synthesis of nitrones, which are useful and environmentally friendly. Catalytic oxidations, condensations, and other useful reactions are described. The nitrones thus obtained are key intermediates for the synthesis of biologically important nitrogen compounds. The second part describes the fundamental transformations of nitrones, which will provide the strategies and means for the construction of nitrogen compounds. The reactions with nucleophiles or radicals, C–H functionalization, and various addition reactions are described. The last reactions are particularly important for highly selective carboncarbon bond formations. 1,3-Dipolar cycloaddition reactions are excluded because the size of the review is limited and excellent reviews have been published in Chemical Reviews.

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Section: Reaction Of Nitrone-functionalized Terminal Alkynesmentioning

confidence: 99%

Synthesis and Transformations of Nitrones for Organic Synthesis

2019

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Recent Developments in the Cyclization of Alkynes and Nitrogen Compounds for the Synthesis of Indole Derivatives

Neto

Zeni

2021

Asian J Org Chem

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This review is intended to highlight the most useful approaches for the synthesis of indole derivatives (azaindoles, carbazoles, carbolines, indazoles, 3H-indoles, indolines, indolizines, isoindoles, and isoindolines), which were described by using transition-metal catalyzed cyclization reactions of alkynes and nitrogen compounds. The methodologies carried out under metal-free conditions will also be illustrated herein. This review will cover the data published mostly in the past decade. Synthesis of 6-AzaindolesAzaindoles, although rare in nature, have attracted a significant attention because some synthetic structures containing this nucleus exhibit biological activities. [17] The synthetic methods describing the preparation of azaindoles are limited. Usually their synthesis was achieved from the cyclization reaction of substrates containing aminopyridines. [18] Transition Metal-Free Synthesis of 6-AzaindolesWe have nominated two methodologies for the preparation of 6-azaindoles, which were developed using alkynes and nitrogen compounds in a metal-free protocol. In the first, an electrophilic cyclization condition, using iodine as an electrophilic source, was applied to 2-(azidomethyl)-3-alkynyl-pyrroles in the preparation of 4-iodo-6-azaindoles 1 (Scheme 1, eq 1). [19] The second approach described the preparation of 2,5-disubstituted 6azaindoles 2 from base-catalyzed intramolecular cyclization of 2-(azidomethyl)-3-alkynyl-pyrroles (Scheme 1, eq 2). [20] 3. Synthesis of 7-Azaindoles Transition Metal-Catalyzed Synthesis of 7-Azaindoles Silver-Catalyzed Synthesis of 7-AzaindolesSilver-catalyzed cyclization reactions of alkynes constitute powerful strategies for the construction of heterocycles. In particular, the 7-azaindoles could be obtained by these approaches. A general method for the preparation of aryl-[a] Dr. J.

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Nitrone and Alkyne Cascade Reactions for Regio‐ and Diastereoselective 1‐Pyrroline Synthesis

et al. 2021

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The synthesis of 1-pyrrolines from N-alkenylnitrones and alkynes has been explored as ar etrosynthetic alternative to traditional approaches.T hese cascade reactions are formal [4 + 1] cycloadditions that proceed through ap roposed dipolar cycloaddition and N-alkenylisoxazoline [3,3']sigmatropic rearrangement. Av ariety of cyclic alkynes and terminal alkynes have been shown to undergo the transformation with N-alkenylnitrones under mild conditions to provide the corresponding spirocyclic and densely substituted 1-pyrrolines with high regio-and diastereoselectivity.M echanistic studies provide insight into the balance of steric and electronic effects that promote the cascade process and control the diastereo-and regioisomeric preferences of the 1-pyrroline products.D iastereoselective derivatization of the 1-pyrrolines prepared by the cascade reaction demonstrate the divergent synthetic utility of the new method.Scheme 1. N-Alkenylisoxazoline approach to 1-pyrroline synthesis.LG = leaving group. EWG = electron-withdrawing group.

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Diastereoselective Synthesis of C3‐Quaternary Indolenines Using α,β‐Unsaturated N‐Aryl Ketonitrones and Activated Alkynes

Cited by 7 publications

References 81 publications

Synthesis and Transformations of Nitrones for Organic Synthesis

Synthesis and Transformations of Nitrones for Organic Synthesis

Recent Developments in the Cyclization of Alkynes and Nitrogen Compounds for the Synthesis of Indole Derivatives

Nitrone and Alkyne Cascade Reactions for Regio‐ and Diastereoselective 1‐Pyrroline Synthesis

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