Palladium-Catalyzed Hydrocarbonylative Cyclization Enabled by Formal Insertion of Aromatic C═N Bonds into Pd–Acyl Bonds

Zhou, Xiaocheng; Chen, Anrong; Du, Wei; Wang, Yawen; Yu, Peng; Huang, Hanmin

doi:10.1021/acs.orglett.9b03503

Cited by 22 publications

(4 citation statements)

References 39 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…A variant of this palladium-catalyzed cyclizative carbonylation of 2-benzylpyridines was accomplished by employing a combination of 8 equiv of formic acid and acetic anhydride to in situ generate the CO. 171 A related palladium-catalyzed hydrocarbonylative cyclization of pyridine-tethered alkenes or dienes was developed by the group of Huang for the synthesis of substituted quinolizinone derivatives (Scheme 113). 172 The optimized reaction conditions entailed the use of Pd(t-Bu 3 P) 2 or PdBr 2 (cod) (cod = 1,5-cyclooctadiene)/t-Bu 3 P as the catalysts and MeONH 2 •HCl as an acid additive. The reaction with 2-(2-vinylphenyl)pyridines 235 was compatible with electronically diverse groups on both rings, although it was less efficient for substrates bearing electron-withdrawing groups on the pyridine ring (Scheme 113, eq 1).…”

Section: Intramolecular Cyclizationsmentioning

confidence: 99%

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

Escolano,

Gaviña,

Alzuet-Piña

et al. 2024

Chem. Rev.

View full text Add to dashboard Cite

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.

show abstract

Section: Intramolecular Cyclizationsmentioning

confidence: 99%

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

Escolano,

Gaviña,

Alzuet-Piña

et al. 2024

Chem. Rev.

View full text Add to dashboard Cite

show abstract

“…For this reason, the development of a synthetic strategy for quinolizinones has been interesting. Numerous studies concerning the chemical synthesis of quinolizinones have been reported; however, most are not cost-effective or multistep, and they require harsh reaction conditions [104,105]. Wang et al synthesized representative quinolizinones, denoted as 2-hydroxy-4H-quinolizin-4-one, scaffolds by integrating three enzymes (Scheme 13) [106].…”

Section: Enzymatic and Chemoenzymatic Approaches For Alkaloidsmentioning

confidence: 99%

Recent Advances in the Synthesis of Marine-Derived Alkaloids via Enzymatic Reactions

et al. 2022

View full text Add to dashboard Cite

Alkaloids are a large and structurally diverse group of marine-derived natural products. Most marine-derived alkaloids are biologically active and show promising applications in modern (agro)chemical, pharmaceutical, and fine chemical industries. Different approaches have been established to access these marine-derived alkaloids. Among these employed methods, biotechnological approaches, namely, (chemo)enzymatic synthesis, have significant potential for playing a central role in alkaloid production on an industrial scale. In this review, we discuss research progress on marine-derived alkaloid synthesis via enzymatic reactions and note the advantages and disadvantages of their applications for industrial production, as well as green chemistry for marine natural product research.

show abstract

“…Then the product ( 3au ) could be oxidized by O 2 in DMSO to afford the corresponding ethyl 1-benzyl-1 H -pyrrole-3-carboxylate 4 in 58% yield . Meanwhile, hydrolysis of the ester gave carboxylic acid 5 in 83% yield . It can be used as a synthetic intermediate for nucleoside derivatives .…”

mentioning

confidence: 99%

“…6k Meanwhile, hydrolysis of the ester gave carboxylic acid 5 in 83% yield. 14 It can be used as a synthetic intermediate for nucleoside derivatives. 2 On the other hand, the 3gs could be facilely transferred to ethyl 3-piperidinecarboxylate 6 in 70% yield through Pd/C-catalyzed hydrogenation and hydrogenolysis.…”

mentioning

confidence: 99%

Brønsted Acid Catalyzed Cyclization of Aminodiazoesters with Aldehydes to 3-Carboxylate-N-Heterocycles

Jiao

Chen

et al. 2020

Org. Lett.

Self Cite

View full text Add to dashboard Cite

A Brønsted acid catalyzed cyclization of aminodiazoesters with aldehydes is described. This reaction features broad substrate generality and functional group compatibility, affording a wide range of 5−7-membered 3-carboxylate-N-heterocycles containing different functional groups. The title products are able to be further elaborated through simple functional group transformations to produce synthetically useful N-heterocycles.N-Heterocycles are privileged scaffolds in synthetic and medicinal chemistry, 1 which not only frequently exist in a wide range of bioactive molecules but also are valuable synthetic building blocks that can be transformed into a series of valuable structures. Especially, the 3-carboxylate-N-heterocycles are well-known scaffolds for constructing a number of bioactive molecules. 2 For example, the 3-nucleoside derivatives prepared from 3-carboxylate-pyrrole display potent inhibition of the human disease-relevant kinases. 2 (R)-Tiagabine featuring piperidine-3-carboxylic acid serves as an efficient GABA uptake inhibitor, 3,4 and the antiplasmodial exhibits the antimalarial activity (Figure 1). 5 In spite of the substantial

show abstract

Palladium-Catalyzed Hydrocarbonylative Cyclization Enabled by Formal Insertion of Aromatic C═N Bonds into Pd–Acyl Bonds

Cited by 22 publications

References 39 publications

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

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

Recent Advances in the Synthesis of Marine-Derived Alkaloids via Enzymatic Reactions

Brønsted Acid Catalyzed Cyclization of Aminodiazoesters with Aldehydes to 3-Carboxylate-N-Heterocycles

Contact Info

Product

Resources

About