[3+2] Cycloaddition Reactions to Indolyl- and Pyrrolyl Derivatives of Dinitrobenzofurazan

Semenyuk, Yu. P.; Kochubei, Alena; Morozov, P. G.; Буров, Олег Н.; Клецкий, М. Е.; Kurbatov, S. V.

doi:10.1007/s10593-015-1645-1

Cited by 8 publications

(2 citation statements)

References 15 publications

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“…Alternatively, conducting the reaction in refluxing MeCN afforded a mixture of 366 and 367 . Similarly, analogs with a pyrrolidinyl function ( 366 and 367 ) were obtained upon reacting the appropriate analog of 365 in MeCN at room temperature (in the darkness) ( Scheme 115 ) [ 155 ].…”

Section: Cyclic Unsaturated 2π-electron Componentsmentioning

confidence: 99%

Azomethine Ylides—Versatile Synthons for Pyrrolidinyl-Heterocyclic Compounds

et al. 2023

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Azomethine ylides are nitrogen-based three-atom components commonly used in [3+2]-cycloaddition reactions with various unsaturated 2π-electron components. These reactions are highly regio- and stereoselective and have attracted the attention of organic chemists with respect to the construction of diverse heterocycles potentially bearing four new contiguous stereogenic centers. This review article complies the most important [3+2]-cycloaddition reactions of azomethine ylides with various olefinic, unsaturated 2π-electron components (acyclic, alicyclic, heterocyclic, and exocyclic ones) reported over the past two decades.

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Section: Cyclic Unsaturated 2π-electron Componentsmentioning

confidence: 99%

Azomethine Ylides—Versatile Synthons for Pyrrolidinyl-Heterocyclic Compounds

et al. 2023

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“…However, using MeCN gave hydropyrrole 185 and pyrrole 186 as a mixture of products in low yields (Scheme 54). 80 A series of substituted N-arylpyrrolidines 188 were synthesized in good chemical yields and very high diastereoselectivities by reaction of imino esters 107 with aryne precursors 187 to give an azomethine ylide that reacted with various electron-deficient alkenes 124 as dipolarophiles. Direct attack of the imino esters 107 to the aryne formed from 187 and protonation of the resulting anion gave azomethine ylides VIII and VIII′.…”

Section: Scheme 53 Stereoselective Synthesis Of Triazolobenzodiazepinesmentioning

confidence: 99%

Current Trends towards the Synthesis of Bioactive Heterocycles and Natural Products Using 1,3-Dipolar Cycloadditions (1,3-DC) with Azomethine Ylides

2017

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In this revision a summary of the trends of the formation of complex or not so complex heterocyclic structures through 1,3-DC of azomethine ylides is described. Diastereo-and enantioselective processes as well as nonasymmetric cycloadditions constitute very important synthetic tools for achieving all these series of compounds. The contents are classified as follows: 1. Introduction 2. Synthesis of spiroxindoles 3. Synthesis of spiropyrrolidines 4. Synthesis of spiropiperidines and piperidines 5. Synthesis of pyrrolidines and fused pyrrolidines 6. Synthesis of pyrrolizidines and indolizidines 7. Synthesis of quinolone and isoquinolines 8. Conclusions

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