Expeditious Synthesis of Highly Substituted Indolizinones via a Palladium-Catalyzed Domino Sequence

Kim, Ikyon; Kim, Kyungsun

doi:10.1021/ol1006778

Cited by 50 publications

(10 citation statements)

References 36 publications

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“…Like the C2 site of indolizine, the alkenyl group in the five‐membered ring of the indolizinone system could also be activated during the metal‐salt‐catalyzed cyclization/1,2‐migration process with propargylic alcohols. Kim reported a highly efficient one‐pot approach to polysubstituted indolizinones 15a from tertiary propargylic alcohols 6 with the aid of a palladium‐catalyzed domino reaction sequence (Scheme ) . This strategy introduces new functional groups at the C2 position of the indolizinone core, expanding the substrate scope for decoration at the C2 site.…”

Section: Synthesis Of Indolizinonesmentioning

confidence: 99%

Cycloisomerization of Pyridine‐Substituted Propargylic Alcohols or Esters To Construct Indolizines and Indolizinones

Wang

Tang

2017

Eur J Org Chem

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Nitrogen‐containing heterocycles are found in a vast number of natural products and biologically active compounds, and have attracted a lot of attention. Among all the reported methods, cycloisomerization transformations involving the activation of alkynes with the aid of transition metals are a very active area in synthetic organic chemistry. This review covers the most important recent advances in the use of metal‐catalyzed or metal‐free cycloisomerizations for the preparation of indolizines and indolizinones from starting substrates consisting of pyridine‐containing propargylic esters or alcohols. Cycloisomerization transformations to heterocycles are very efficient and atom‐economic, and we hope that this review will result in further focused research to widen the application of indolizines and indolizinones.

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Section: Synthesis Of Indolizinonesmentioning

confidence: 99%

Cycloisomerization of Pyridine‐Substituted Propargylic Alcohols or Esters To Construct Indolizines and Indolizinones

Wang

Tang

2017

Eur J Org Chem

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“…Aryl iodides were incorporated into the final product in the palladium-catalyzed synthesis of indolizinones from propargylic alcohols, reported by Kim. 79 As shown in Scheme 29, the tertiary propargylic alcohol 147 was cyclized to the indolizinone products 150 under basic conditions in the presence of the aryl iodide and catalytic tetrakis(triphenylphosphine)palladium(0) [Pd(PPh 3 ) 4 ]. Mechanistically, a palladium(II)-aryl species might first induce a 5-endo-dig cyclization to give the intermediates 148.…”

Section: Scheme 28 Dihydropyridine Formation 78mentioning

confidence: 99%

Transition-Metal-Catalyzed Functionalization of Propargylic Alcohols and Their Derivatives

Bauer

2012

Synthesis

166

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Propargylic alcohols are valuable starting materials in organic synthesis; they are easily accessible and can be functionalized further, either through the triple bond or the alcohol functionality. Certain transition metals such as ruthenium or gold have an affinity for propargylic alcohols or alkyne units, which allows for catalytic activation of these substance classes. This review article provides a survey of various transition-metal-catalyzed functionalizations of propargylic alcohols with an emphasis on the latest literature. Examples of nucleophilic propargylic substitution reactions, allene formation, addition and coupling reactions, cyclization reactions, Meyer-Schuster, Rupe and redox-isomerization reactions are given in the article, along with the scope and limitations of the corresponding transformations and mechanistic considerations.

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“…Polysubstituted indolizinones were synthesized by Kim and Kim 85 from readily available tertiary propargylic alcohols in a one-pot procedure by employing a palladiumcatalyzed domino cyclization reaction. 14 In this protocol, aminopalladation and reductive elimination were successfully coupled with 1,2-rearrangement.…”

Section: Scheme 36mentioning

confidence: 99%

Recent Developments in Palladium-Catalyzed Formation of Five- and Six-Membered Fused Heterocycles

Majumdar¹,

Samanta²,

Sinha³

2012

Synthesis

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Palladium-mediated cyclization reactions have been recognized as some of the simplest and useful tools for regio-as well as stereoselective syntheses of carbo-and heterocyclic compounds. In the multi-step syntheses of natural products it is frequently used as one of the most important steps. In this review article, we have summarized the various ways of constructing five-and six-membered heterocyclic rings by palladium-catalyzed intramolecular cyclizations published between 2008 and 2010.

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Expeditious Synthesis of Highly Substituted Indolizinones via a Palladium-Catalyzed Domino Sequence

Abstract: A direct one-pot approach to polysubstituted indolizinones from tertiary propargylic alcohols using a palladium-catalyzed domino process involving aminopalladation, reductive elimination, and 1,2-shift is described.

Cited by 50 publications

References 36 publications

Cycloisomerization of Pyridine‐Substituted Propargylic Alcohols or Esters To Construct Indolizines and Indolizinones

Cycloisomerization of Pyridine‐Substituted Propargylic Alcohols or Esters To Construct Indolizines and Indolizinones

Transition-Metal-Catalyzed Functionalization of Propargylic Alcohols and Their Derivatives

Recent Developments in Palladium-Catalyzed Formation of Five- and Six-Membered Fused Heterocycles

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