Synthetic Strategies for the Construction of Indolizines and Indolizine‐fused Compounds: Thienoindolizines and Indolizinoindoles

Nevskaya, Alisa A.; Zinoveva, Anna D.; Van der Eycken, Erik V.; Voskressensky, Leonid G.

doi:10.1002/ajoc.202300359

Cited by 6 publications

(2 citation statements)

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“…Indolizinoindole derivatives have also shown significant biological activity, as evidenced by numerous publications. [18][19][20] The indolizino [8,7-b]indole skeleton has been found in natural bioactive substances, which possess notable analgesic, [21] antitumor, [22] and antibacterial [23] effects.…”

Section: Introductionmentioning

confidence: 99%

Synthesis Of Dipyrrolobenzo[1,2‐a : 2′,1′‐c][1,4]diazepine Scaffold Via Three‐Component Reaction

Zinoveva,

Borisova,

Podchufarova

et al. 2024

Asian J Org Chem

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A three component reaction employing readily available starting materials: 2‐(1‐pyrrolyl)benzylamine, arylglyoxal monohydrates and electron‐deficient alkenes in the synthesis of dipyrrolobenzo[1,2‐a:2',1'‐c][1,4]diazepines ‐ previously undescribed system and indolo[2,1‐c]pyrrolo[1,2‐a][1,4]benzodiazepine derivatives have been shown. Domino reactions of pyrrolo[1,2‐a][1,4]benzodiazepines with electron‐deficient alkenes has been proposed as another approach. The applicability of the three‐component reaction for the synthesis of indolizino[8,7‐b]indole derivatives from tryptamine has been studied. The in vitro biological activity of title compounds has been tested.

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Section: Introductionmentioning

confidence: 99%

Synthesis Of Dipyrrolobenzo[1,2‐a : 2′,1′‐c][1,4]diazepine Scaffold Via Three‐Component Reaction

Zinoveva,

Borisova,

Podchufarova

et al. 2024

Asian J Org Chem

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“…27 Under metal-, external oxidant-, and base-free conditions, pyridine rings were conveniently fused with enaminones, affording diverse functionalized indolizines straightforwardly (Scheme 1c). 28,29 Although the preliminary mechanism investigation indicated that the in situ generated pyridine-Bpin radical (Py-Bpin˙) triggered the reaction, the underlying precise mechanisms, particularly those beyond the initial radical generation, remain elusive and amenable to address. For example, it has been well-known that Bpin˙ can migrate from pyridines to the carbonyl groups, affording OBpin-ligated ketyl radicals.…”

Section: Introductionmentioning

confidence: 99%

A pyridine-boryl radical mediated cascade reaction towards the synthesis of indolizines: a computational mechanistic analysis

Zhang,

Cao,

Wei

et al. 2024

Org. Chem. Front.

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Recent Advances in the Development of Indolizine Scaffolds: Synthetic Methodology and Mechanistic Insights

Huang,

Li,

et al. 2024

Chin. J. Chem.

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Comprehensive SummaryIndolizine is a nitrogen‐containing heterocycle with strong aromaticity, possessing a delocalized 10π‐electron system. Based on the indolizine scaffolds, numerous molecules with biological activity and organic functional materials have been synthesized. Since 2016, over 110 papers have been published on the synthesis of indolizine scaffolds, but the reviews on synthesizing indolizine scaffolds have been incomplete and not up‐to‐date. Herein, from the perspective of the structure of indolizine with the combination of pyrrole and pyridine ring, we focus on the construction of indolizine scaffolds through the diversity of starting substrates, including pyridine derivatives (N1‐substituted pyridinium salt derivatives, C2‐substituted pyridine derivatives, N1‐ and C2‐free substituted pyridine derivatives), pyrrole derivatives and unoriginal ring substrates. Furthermore, the corresponding reaction mechanisms of synthetic methodologies are also elaborated. Therefore, this review not only paves the way for indolizine synthesis but also provides insight into exploring new reaction modes for constructing nitrogen‐containing heterocycles. Key ScientistsIndolizine was discovered by Angeli in 1890 and first prepared by Scholtz in 1912 from α‐picoline and acetic anhydride. A general approach was developed by Chichibabin in 1927, that is of practical value for the preparation of 2‐alkyl‐ or 2‐arylindolizines. The Chichibabin reaction was the ring closure of quaternary pyridinium halides. At the begining of the 21st century, Basavaiah introduced a new dimension in the Baylis‐Hillman chemistry leading to a novel facile convenient methodology for synthesis of indolizine scaffolds in one‐pot operation. In 2010, Barluenga reported Cu(I)‐catalyzed regioselective [3+2] cyclization of unsubstituted pyridines toward alkenyldiazoacetates leading to functionalized indolizine derivatives, that was the first successful example of metal‐catalyzed cyclization of a π‐deficient heterocyclic system with alkenyldiazo compounds. In 2019 and 2022, Xi and Liu exploited the methods of non‐pyridine derivatives as starting materials to synthesize indolizines, respectively. In 2022, Guo developed an environmentally benign electrooxidative approach for constructing formyl‐ and acyl‐substituted indolizines.

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Synthetic Strategies for the Construction of Indolizines and Indolizine‐fused Compounds: Thienoindolizines and Indolizinoindoles

Cited by 6 publications

References 112 publications

Synthesis Of Dipyrrolobenzo[1,2‐a : 2′,1′‐c][1,4]diazepine Scaffold Via Three‐Component Reaction

Synthesis Of Dipyrrolobenzo[1,2‐a : 2′,1′‐c][1,4]diazepine Scaffold Via Three‐Component Reaction

A pyridine-boryl radical mediated cascade reaction towards the synthesis of indolizines: a computational mechanistic analysis

Recent Advances in the Development of Indolizine Scaffolds: Synthetic Methodology and Mechanistic Insights

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