Iron-Catalyzed Indolizine Synthesis from Pyridines, Diazo Compounds, and Alkynes

Douglas, Tim; Pordea, Anca; Dowden, James

doi:10.1021/acs.orglett.7b03252

Cited by 62 publications

(22 citation statements)

References 21 publications

(34 reference statements)

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“…developed a general method for the synthesis of indolizine using rhodium(III)‐catalyst by oxidative annulation of pyridinium ylide with alkynes. Later, Dowden and co‐workers reported iron(III)‐catalysed synthesis of indolizines from commercially available alkyne, pyridine and diazo compound .…”

Section: Introductionmentioning

confidence: 93%

Catalyst free Synthesis of Highly Functionalized Indolizines from In Situ Generated Pyridinium Ylides via One‐Pot Multicomponent Reaction

Ramesh

Devi²,

Velusamy

et al. 2019

ChemistrySelect

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A base-promoted one-pot three-component domino reaction of in situ generated pyridinium ylides with α-oxoketene dithioacetals (AKDTAs) lead to synthesis of indolizine derivatives. In this one-pot transformation, three new bonds and one new ring was efficiently formed in one sequence. The current method provides a simple, convenient route for the synthesis of biologically important indolizine derivatives without using any catalyst in good yield. The synthesized compound 4 g was confirmed by single crystal X-ray analysis.[a] V.

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Section: Introductionmentioning

confidence: 93%

Catalyst free Synthesis of Highly Functionalized Indolizines from In Situ Generated Pyridinium Ylides via One‐Pot Multicomponent Reaction

Ramesh

Devi²,

Velusamy

et al. 2019

ChemistrySelect

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“…In 2017, Dowden et al reported a Fe-catalyzed three-component [3 + 2]-cycloaddition for the synthesis of indolizine derivatives from commercially available alkynes 21, pyridines 2, and ethyl diazoacetate 33 a (EDA) (Scheme 11). [24] The using of inexpensive and abundant iron catalyst [Fe(TPP)Cl] (TPP = tetraphenylporphyrin), which could be reduced to as little as 0.25 mol%, showed competing potential of this method for further applications. Mechanism study of this work demonstrated the importance of the catalyst in promoting the ylide formation over the background reactivity, for example, [3 + 2]cycloaddition of the diazo compounds with electrophilic alkynes.…”

Section: Fe-catalyzed [3 + 2]-cycloadditionmentioning

confidence: 99%

[3+2]‐Cycloaddition of Catalytically Generated Pyridinium Ylide: A General Access to Indolizine Derivatives

Dong

2020

Asian J Org Chem

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Pyridinium ylide is a versatile building block in synthetic organic chemistry, especially in the synthesis of N‐heterocycles. In this minireview, we have summarized the advances of [3+2]‐cycloaddition of catalytically generated pyridinium ylide for the synthesis of indolizines (since 1970s). Accordingly, the ylide discussed in this article is generated in situ from carbene precursors and N‐heteroarenes under catalytic conditions, including photocatalysis/thermocatalysis, and metal‐catalysis. The metal‐catalyzed version is the main focus, which is classified and summarized based on the type of dipolarophiles, alkyne and alkene, each class is further subdivided according to the metal catalysts used in these reactions. The analogous [3+2]‐cycloaddition of vinyl metal carbene with pyridines, the formation of pyridinium ylide with other type of carbene precursors or with different N‐heteroarenes, have been also included herein separately.

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“…When 1,3-dipolar cycloaddition of pyridinium ylides with electron-deficient olefins or alkynes is followed by oxidative aromatization (spontaneous or chemically induced) a convergent and straightforward access toward functionalized indolizines is arranged. Many excellent examples of this synthetic sequence (cycloaddition/aromatization) have been published (for examples see [75,[77][78][79][80][81][82]) as indolizine is an important skeletal structure present in many natural and synthetic bioactive molecules (for examples see [83][84][85][86][87][88][89][90][91][92][93]) and in material with photochemical properties [94][95][96][97][98][99][100][101][102]. Pivina and co-authors recently reported quantum chemical calculations on the spatial and electronic structure of pyridinium ylides, as well as the modelling of their1,3-dipolar cycloadddition reactions.…”

Section: Pyridinium Ylidesmentioning

confidence: 99%

Nucleophilic Dearomatization of Activated Pyridines

2018

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Amongst nitrogen heterocycles of different ring sizes and oxidation statuses, dihydropyridines (DHP) occupy a prominent role due to their synthetic versatility and occurrence in medicinally relevant compounds. One of the most straightforward synthetic approaches to polysubstituted DHP derivatives is provided by nucleophilic dearomatization of readily assembled pyridines. In this article, we collect and summarize nucleophilic dearomatization reactions of - pyridines reported in the literature between 2010 and mid-2018, complementing and updating previous reviews published in the early 2010s dedicated to various aspects of pyridine chemistry. Since functionalization of the pyridine nitrogen, rendering a (transient) pyridinium ion, is usually required to render the pyridine nucleus sufficiently electrophilic to suffer the attack of a nucleophile, the material is organized according to the type of N-functionalization. A variety of nucleophilic species (organometallic reagents, enolates, heteroaromatics, umpoled aldehydes) can be productively engaged in pyridine dearomatization reactions, including catalytic asymmetric implementations, providing useful and efficient synthetic platforms to (enantioenriched) DHPs. Conversely, pyridine nitrogen functionalization can also lead to pyridinium ylides. These dipolar species can undergo a variety of dipolar cycloaddition reactions with electron-poor dipolarophiles, affording polycyclic frameworks and embedding a DHP moiety in their structures.

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Iron-Catalyzed Indolizine Synthesis from Pyridines, Diazo Compounds, and Alkynes

Cited by 62 publications

References 21 publications

Catalyst free Synthesis of Highly Functionalized Indolizines from In Situ Generated Pyridinium Ylides via One‐Pot Multicomponent Reaction

Catalyst free Synthesis of Highly Functionalized Indolizines from In Situ Generated Pyridinium Ylides via One‐Pot Multicomponent Reaction

[3+2]‐Cycloaddition of Catalytically Generated Pyridinium Ylide: A General Access to Indolizine Derivatives

Nucleophilic Dearomatization of Activated Pyridines

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