One-pot Sonogashira coupling, hydroamination of alkyne and intramolecular C H arylation reactions toward the synthesis of indole-fused benzosultams

Debnath, Sudarshan

doi:10.1016/j.tetlet.2018.04.081

Cited by 10 publications

(2 citation statements)

References 27 publications

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“…In 2018, Mondal reported a one‐pot Sonogashira coupling/ hydroamination/C–H arylation reactions for the synthesis of indole‐fused benzosultam (Scheme 4a). [ 37 ] The one‐pot‐two‐step procedure allowed facile access of indole‐fused seven‐membered benzosultams in excellent yields. Further investigations reviewed that the indole moiety was made from the domino Sonogashira coupling and 5‐ endo‐dig cyclization reaction, and the 7‐membered benzosultam was formed via C–H arylation with Pd catalyst.…”

Section: Classical Sonogashira Coupling Reactionsmentioning

confidence: 99%

Recent Expedition inPd‐CatalyzedSonogashira Coupling and Related Processes^†

2023

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Sonogashira cross-coupling protocol, typically showing the reaction between aryl/vinyl halide and terminal alkyne, has been a widely used protocol for constructing C(sp 2 )-C(sp) bond. The resulting internal alkynes are highly versatile for reaching differently functionalized alkyne-containing scaffolds or serving as valuable synthetic synthons to many other functional groups. It is worth noting that products originated from this coupling reaction are mostly applicable to be transformed into corresponding Z-alkene, alkane, or heterocyclic moieties in natural product syntheses. The reaction conditions and catalyst systems are able to be tweaked in order to facilitate the activation of steric hindered and/or electron-rich electrophiles. Pd-catalyzed copper-free Sonogashira coupling reaction has caught increasing attention as the improved method can be more environmentally friendly. What is more, the conditions of the coupling reaction can be readily amended to allow the fusion of other carbonylation or decarboxylation step in the catalytic cycle, and thus allow more complex yet versatile convergent synthesis to proceed in an operationally simple one-pot manner.

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Section: Classical Sonogashira Coupling Reactionsmentioning

confidence: 99%

Recent Expedition inPd‐CatalyzedSonogashira Coupling and Related Processes^†

2023

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“…In 2018, Mondal and co-workers further extended their one-pot process towards the construction of indole-fused seven-membered benzosultams from easily available starting materials ( Scheme 12 ) [ 89 ]. The synergistic combination of Pd(PPh 3 ) 2 Cl 2 and CuI catalysts in DMF was found to be crucial for high reaction conversion.…”

Section: Transition Metal-catalyzed Benzosultam Synthesismentioning

confidence: 99%

Recent Advances in Catalytic Synthesis of Benzosultams

Zhao

2020

Molecules

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Benzosultams represent one category of multi-heteroatom heterocyclic scaffolds, which have been frequently found in pharmaceuticals, agricultural agents, and chiral catalysts. Given the diversely significant functions of these compounds in organic and medicinal chemistry, great efforts have been made to develop novel catalytic systems for the efficient construction of benzosultam motifs over the past decades. Herein, in this review, we mainly summarize the recent advances in the field of catalytic synthesis of benzosultams from 2017 to August of 2020, with an emphasis on the scopes and mechanisms of representative reactions.

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Development of Synthetic Approaches to Biaryl Sultams via CH Functionalization

Gupta¹,

Laha²

2022

Handbook of CH-Functionalization

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Biaryl sultams represent a privileged molecular scaffold in drug discovery owing to their potential as a clinical candidate. Various developments toward the synthesis of diverse biaryl sultams including metal‐catalyzed and metal‐free CH functionalization involving CC/CN bond formation or annulative cyclization have been advanced in recent time. However, a transition metal‐catalyzed direct CH functionalization approach remains a powerful variant and has been utilized tremendously for the past several decades. The postsynthetic transformations of biaryl sultams to drug‐like molecules offer a tremendous possibility in drug discovery. In this article, we aim to provide an overview of various developments made in the synthetic approaches to biaryl sultams via CH functionalization, with a futuristic emphasis on their postsynthetic utility in accessing (hetero)biaryls containing an ortho ‐sulfonamide or amine functionality, a promising and potentially useful molecular scaffold in therapeutic discovery. The current challenges and a future perspective are also discussed briefly.

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One-pot Sonogashira coupling, hydroamination of alkyne and intramolecular C H arylation reactions toward the synthesis of indole-fused benzosultams

Cited by 10 publications

References 27 publications

Recent Expedition inPd‐CatalyzedSonogashira Coupling and Related Processes^†

Recent Expedition inPd‐CatalyzedSonogashira Coupling and Related Processes^†

Recent Advances in Catalytic Synthesis of Benzosultams

Development of Synthetic Approaches to Biaryl Sultams via CH Functionalization

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One-pot Sonogashira coupling, hydroamination of alkyne and intramolecular C H arylation reactions toward the synthesis of indole-fused benzosultams

Cited by 10 publications

References 27 publications

Recent Expedition inPd‐CatalyzedSonogashira Coupling and Related Processes†

Recent Expedition inPd‐CatalyzedSonogashira Coupling and Related Processes†

Recent Advances in Catalytic Synthesis of Benzosultams

Development of Synthetic Approaches to Biaryl Sultams via CH Functionalization

Contact Info

Product

Resources

About

Recent Expedition inPd‐CatalyzedSonogashira Coupling and Related Processes^†

Recent Expedition inPd‐CatalyzedSonogashira Coupling and Related Processes^†