Application of α-amino acids for the transition-metal-free synthesis of pyrrolo[1,2-a]quinoxalines

Liu, Huanhuan; Zhou, Fei-Yu; Luo, Wen; Chen, Yuxin; Zhang, Chenyang; Ma, Chen

doi:10.1039/c7ob01688c

Cited by 29 publications

(16 citation statements)

References 46 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…As α‐amino acids were competent substrates for synthesis of pyrrolo[1,2‐ a ]quinoxalines, [7] the use of isosteric α‐hydroxy acids should be considered. In 2020, Jung and co‐workers reported a method for oxidative coupling of 1‐(2‐aminoaryl)pyrroles and α‐hydroxy acids in the presence of tert ‐butyl hydroperoxide (TBHP) oxidant [8] .…”

Section: Recent Methods For Synthesis Of Pyrrolo/indolo[12‐a]quinoxal...mentioning

confidence: 99%

Recent Examples in the Synthesis and Functionalization of C−H Bonds in Pyrrolo/Indolo [1,2‐a]Quinoxalines

Nguyen

2022

ChemistrySelect

View full text Add to dashboard Cite

As important molecules that find ubiquitous applications in organic synthesis, medicinal chemistry, and functional materials, pyrrolo/indolo [1,2‐a]quinoxalines have attracted substantial attention. This review features recent development, since 2019, on methods for synthesis of such fused N,N‐heterocycles. In addition, the latest examples related to direct functionalization of C−H bonds in pyrrolo/indolo [1,2‐a]quinoxalines will be discussed as well.

show abstract

Section: Recent Methods For Synthesis Of Pyrrolo/indolo[12‐a]quinoxal...mentioning

confidence: 99%

Recent Examples in the Synthesis and Functionalization of C−H Bonds in Pyrrolo/Indolo [1,2‐a]Quinoxalines

Nguyen

2022

ChemistrySelect

View full text Add to dashboard Cite

show abstract

“…Later, Ma and collaborators (2017) contemplated a succinct methodology for the proficient preparation of pyrrolo[1,2‐a]quinoxalines from promptly accessible α‐amino acids and 2‐(1H‐pyrrol‐1‐yl)anilines in the absence of transition metals in good to significant yield (Scheme 144). [162] …”

Section: C−h Functionalization Of Pyrrolesmentioning

confidence: 99%

Recent Advances in Functionalization of Pyrroles and their Translational Potential

Hunjan

Panday

Gupta

et al. 2021

The Chemical Record

View full text Add to dashboard Cite

Among the known aromatic nitrogen heterocycles, pyrrole represents a privileged aromatic heterocycle ranging its occurrence in the key component of “pigments of life” to biologically active natural products to active pharmaceuticals. Pyrrole being an electron‐rich heteroaromatic compound, its predominant functionalization is legendary to aromatic electrophilic substitution reactions. Although a few excellent reviews on the functionalization of pyrroles including the reports by Baltazzi in 1963, Casiraghi and Rassu in 1995, and Banwell in 2006 are available, they are fragmentary and over fifteen years old, and do not cover the modern aspects of catalysis. A review covering a comprehensive package of direct functionalization on pyrroles via catalytic and non‐catalytic methods including their translational potential is described. Subsequent to statutory yet concise introduction, the classical functionalization on pyrroles using Lewis acids largely following an ionic mechanism is discussed. The subsequent discussion follows the various metal‐catalyzed C−H functionalization on pyrroles, which are otherwise difficult to implement by Lewis acids. A major emphasize is given on the radical based pyrrole functionalization under metal‐free oxidative conditions, which is otherwise poorly highlighted in the literature. Towards the end, the current development of pyrrole functionalization under photocatalyzed and electrochemical conditions is appended. Only a selected examples of substrates and important mechanisms are discussed for different methods highlighting their scopes and limitations. The aromatic nucleophillic substitution on pyrroles (being an electron‐rich heterocycle) happened to be the subject of recent investigations, which has also been covered accentuating their underlying conceptual development. Despite great achievements over the past several years in these areas, many challenges and problems are yet to be solved, which are all discussed in summary and outlook.

show abstract

“…Ma et al. described a practical protocol for the synthesis of pyrrolo[1,2‐ a ]quinoxalines 199 from readily available α‐amino acids 164 and 2‐(1 H ‐pyrrol‐1‐yl)anilines 198 under metal‐free conditions with a wide substrate scope and a broad range of functional group tolerance (Scheme ) …”

Section: Decarboxylative Reactions Of α‐Amino Acids Via Radical Pathwaysmentioning

confidence: 99%

Recent Advances on Diverse Decarboxylative Reactions of Amino Acids

et al. 2019

View full text Add to dashboard Cite

This review aims to report recent advances on decarboxylative reactions of amino acids catalyzed by transitionm etals or non-metals and the growing opportunities they present in the construction of complexc hemical scaffolds for applications encompassing natural product synthesis, synthetic methodology development, and functional materials. Different decarboxylative reactions have been highlighted such as radical, photoredox and metal and metal-free coupling reactions.e tc. Ther eview is divided into two main sections:o ne deals with reactions via radical pathways andt he other via azomethine ylide pathways.T he reactions have been discussed in more detail with particular emphasis on their useful applications andm echanistic illustrations.

show abstract

Application of α-amino acids for the transition-metal-free synthesis of pyrrolo[1,2-a]quinoxalines

Cited by 29 publications

References 46 publications

Recent Examples in the Synthesis and Functionalization of C−H Bonds in Pyrrolo/Indolo [1,2‐a]Quinoxalines

Recent Examples in the Synthesis and Functionalization of C−H Bonds in Pyrrolo/Indolo [1,2‐a]Quinoxalines

Recent Advances in Functionalization of Pyrroles and their Translational Potential

Recent Advances on Diverse Decarboxylative Reactions of Amino Acids

Contact Info

Product

Resources

About