Cycloaddition of Huisgen 1,4-dipoles: synthesis and rapid epimerization of functionalized spiropyrido[2,1-<i>b</i>][1,3]oxazine-pyrroles and related products

Galeev, A. R.; Moroz, A. A.; Дмитриев, М. В.; Масливец, А. Н.

doi:10.1039/d1ra08384h

Cited by 3 publications

(4 citation statements)

References 65 publications

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“…The authors also extended this methodology to N-alkyl isatins, 1H-indeno[1,2-b]quinoxalin-11-one and isatylidene malononitrile as dipolarophiles with similar results. 142 A third example regarding cycloaddition reactions of pyridine-derived Huisgen 1,4-dipoles 185 entailed their reaction with tryptanthrins 190 as dipolarophiles, to render spirooxazine derivatives 191 in good yields with excellent diastereoselectivity (Scheme 97, eq 3). 143 Huisgen's dipoles derived from isoquinoline also performed successfully in this three-component reaction.…”

Section: Other Types Of N-heterocyclic Dipolesmentioning

confidence: 99%

“…The same pyridine-derived Huisgen 1,4-dipoles 185 reacted with 1 H -pyrrole-2,3-diones 188 as dipolarophiles in a regioselective (4 + 2) cycloaddition process (Scheme , eq 2) . A variety of 1 H -pyrrole-2,3-diones bearing electronically diverse substituents at the 4-, 5-, and N 1 -positions were employed, without significantly affecting the yields of the spirocyclic cycloadducts 189 albeit they were obtained as mixtures of diastereoisomers.…”

Section: Cycloaddition Reactions and Annulationsmentioning

confidence: 99%

“…The same pyridine-derived Huisgen 1,4-dipoles 185 reacted with 1 H -pyrrole-2,3-diones 188 as dipolarophiles in a regioselective (4 + 2) cycloaddition process ( Scheme 97 , eq 2). 142 A variety of 1 H -pyrrole-2,3-diones bearing electronically diverse substituents at the 4-, 5-, and N 1 -positions were employed, without significantly affecting the yields of the spirocyclic cycloadducts 189 albeit they were obtained as mixtures of diastereoisomers. The authors also extended this methodology to N -alkyl isatins, 1 H -indeno[1,2- b ]quinoxalin-11-one and isatylidene malononitrile as dipolarophiles with similar results.…”

Section: Cycloaddition Reactions and Annulationsmentioning

confidence: 99%

“…The authors also extended this methodology to N -alkyl isatins, 1 H -indeno[1,2- b ]quinoxalin-11-one and isatylidene malononitrile as dipolarophiles with similar results. 142 …”

Section: Cycloaddition Reactions and Annulationsmentioning

confidence: 99%

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Recent Strategies in the Nucleophilic Dearomatization of Pyridines, Quinolines, and Isoquinolines

Escolano,

Gaviña,

Alzuet-Piña

et al. 2024

Chem. Rev.

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Dearomatization reactions have become fundamental chemical transformations in organic synthesis since they allow for the generation of three-dimensional complexity from two-dimensional precursors, bridging arene feedstocks with alicyclic structures. When those processes are applied to pyridines, quinolines, and isoquinolines, partially or fully saturated nitrogen heterocycles are formed, which are among the most significant structural components of pharmaceuticals and natural products. The inherent challenge of those transformations lies in the low reactivity of heteroaromatic substrates, which makes the dearomatization process thermodynamically unfavorable. Usually, connecting the dearomatization event to the irreversible formation of a strong C−C, C− H, or C−heteroatom bond compensates the energy required to disrupt the aromaticity. This aromaticity breakup normally results in a 1,2-or 1,4-functionalization of the heterocycle. Moreover, the combination of these dearomatization processes with subsequent transformations in tandem or stepwise protocols allows for multiple heterocycle functionalizations, giving access to complex molecular skeletons. The aim of this review, which covers the period from 2016 to 2022, is to update the state of the art of nucleophilic dearomatizations of pyridines, quinolines, and isoquinolines, showing the extraordinary ability of the dearomative methodology in organic synthesis and indicating their limitations and future trends.

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Section: Other Types Of N-heterocyclic Dipolesmentioning

confidence: 99%

Section: Cycloaddition Reactions and Annulationsmentioning

confidence: 99%

Section: Cycloaddition Reactions and Annulationsmentioning

confidence: 99%

“…The authors also extended this methodology to N -alkyl isatins, 1 H -indeno[1,2- b ]quinoxalin-11-one and isatylidene malononitrile as dipolarophiles with similar results. 142 …”

Section: Cycloaddition Reactions and Annulationsmentioning

confidence: 99%

See 2 more Smart Citations

Recent Strategies in the Nucleophilic Dearomatization of Pyridines, Quinolines, and Isoquinolines

Escolano,

Gaviña,

Alzuet-Piña

et al. 2024

Chem. Rev.

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Five-membered ring systems: pyrroles and benzo analogs

Lopchuk

2023

Progress in Heterocyclic Chemistry

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The unique reactivity of 5,6-unsubstituted 1,4-dihydropyridine in the Huisgen 1,4-diploar cycloaddition and formal [2 + 2] cycloaddition

Chen

Zheng

Han

et al. 2023

Beilstein J. Org. Chem.

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The three-component reaction of isoquinolines, dialkyl acetylenedicarboxylates, and 5,6-unsubstituted 1,4-dihydropyridines in acetonitrile at room temperature afforded functionalized isoquinolino[1,2-f][1,6]naphthyridines in good yields and with high diastereoselectivity. More importantly, the formal [2 + 2] cycloaddition reaction of dialkyl acetylenedicarboxylates and 5,6-unsubstituted 1,4-dihydropyridines in refluxing acetonitrile gave unique 2-azabicyclo[4.2.0]octa-3,7-dienes as major products and 1,3a,4,6a-tetrahydrocyclopenta[b]pyrroles as minor products via further rearrangement.

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Cycloaddition of Huisgen 1,4-dipoles: synthesis and rapid epimerization of functionalized spiropyrido[2,1-b][1,3]oxazine-pyrroles and related products

Abstract: Rapid epimerization of cycloadducts from Huisgen 1,4-dipoles has been investigated through the synthesis of new spiropyrido[2,1-b][1,3]oxazine-pyrroles and repetition of syntheses from the literature.

Cited by 3 publications

References 65 publications

Recent Strategies in the Nucleophilic Dearomatization of Pyridines, Quinolines, and Isoquinolines

Recent Strategies in the Nucleophilic Dearomatization of Pyridines, Quinolines, and Isoquinolines

Five-membered ring systems: pyrroles and benzo analogs

The unique reactivity of 5,6-unsubstituted 1,4-dihydropyridine in the Huisgen 1,4-diploar cycloaddition and formal [2 + 2] cycloaddition

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