Electrophilic Substitution Reactions of Indoles

Sundberg, Richard J.

doi:10.1007/7081_2010_52

Cited by 49 publications

(29 citation statements)

References 365 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Inspired by the carboxylative cyclization of propargylic alcohols and propargylamines,8 we envisioned the alternative use of a carbon nucleophile, thus resulting in a CC bond‐forming transformation. The C3‐position of indole‐rings are competent nucleophiles in a number of transformations,9 while alkynes have been established as good electrophiles under gold catalysis 10. To this end, 2‐alkynyl indoles were selected as potential starting materials for this CC bond‐forming transformation furnishing multicyclic heteroaromatic ring systems with CO 2 fixation (Scheme ).…”

Section: Methodsmentioning

confidence: 99%

Organocatalyzed CO₂ Trapping Using Alkynyl Indoles

et al. 2015

View full text Add to dashboard Cite

The first organocatalyzed trapping of CO2 through C-C and C-O bond formation is reported. Alkynyl indoles together with catalytic amounts of an organic base and five equivalents of CO2 resulted in the formation new heterocyclic structures. These tricyclic indole-containing products were successfully prepared under mild reaction conditions from aromatic, heteroaromatic, and aliphatic alkynyl indoles with complete regioselectivity. Further investigations suggest that C-C bond formation is the initial intermolecular step, followed by lactone-forming C-O bond formation.

show abstract

Section: Methodsmentioning

confidence: 99%

Organocatalyzed CO₂ Trapping Using Alkynyl Indoles

et al. 2015

View full text Add to dashboard Cite

show abstract

“…Based on the ability of this reactive intermediate to give rise to sulfonium ylides upon reaction with thiol/thioether nucleophiles [9b, 16] and the well established nucleophilicity of indoles at the C3 site, [17] a plausible mechanism for the Mb-catalyzed indole C—H functionalization is proposed in Scheme 3. According to it, reaction of the catalytically active ferrous Mb ( I ) with the diazo reagent leads to the heme-carbene intermediate II , which undergoes nucleophilic attack by the indole substrate to yield the zwitterionic species III .…”

mentioning

confidence: 99%

Myoglobin‐Catalyzed C−H Functionalization of Unprotected Indoles

et al. 2018

View full text Add to dashboard Cite

Functionalized indoles are recurrent motifs in bioactive natural products and pharmaceuticals. While transition metal-catalyzed carbene transfer has provided an attractive route to afford C3-functionalized indoles, these protocols are viable only in the presence of N-protected indoles, owing to competition from the more facile N-H insertion reaction. Herein, a biocatalytic strategy for enabling the direct C-H functionalization of unprotected indoles is reported. Engineered variants of myoglobin provide efficient biocatalysts for this reaction, which has no precedents in the biological world, enabling the transformation of a broad range of indoles in the presence of ethyl α-diazoacetate to give the corresponding C3-functionalized derivatives in high conversion yields and excellent chemoselectivity. This strategy could be exploited to develop a concise chemoenzymatic route to afford the nonsteroidal anti-inflammatory drug indomethacin.

show abstract

“…Molecular orbital studies showed that the 3-position of indole is more reactive towards the electrophilic substitution reactions. Indoles can undergo N-substitution reactions under basic conditions owing to the slightly acidic nature of the-NH bond in indole [6]. The first synthesis of indole was accomplished in 1866 by Adolf von Baeyer [7].…”

Section: Indole and Its Pharmacological Significancementioning

confidence: 99%

Role of Indole Scaffolds as Pharmacophores in the Development of Anti-Lung Cancer Agents

Dhuguru

Skouta

2020

Molecules

View full text Add to dashboard Cite

Lung cancer is the leading cause of death in men and women worldwide, affecting millions of people. Between the two types of lung cancers, non-small cell lung cancer (NSCLC) is more common than small cell lung cancer (SCLC). Besides surgery and radiotherapy, chemotherapy is the most important method of treatment for lung cancer. Indole scaffold is considered one of the most privileged scaffolds in heterocyclic chemistry. Indole may serve as an effective probe for the development of new drug candidates against challenging diseases, including lung cancer. In this review, we will focus on discussing the existing indole based pharmacophores in the clinical and pre-clinical stages of development against lung cancer, along with the synthesis of some of the selected anti-lung cancer drugs. Moreover, the basic mechanism of action underlying indole based anti-lung cancer treatment, such as protein kinase inhibition, histone deacetylase inhibition, DNA topoisomerase inhibition, and tubulin inhibition will also be discussed.

show abstract

Electrophilic Substitution Reactions of Indoles

Cited by 49 publications

References 365 publications

Organocatalyzed CO₂ Trapping Using Alkynyl Indoles

Organocatalyzed CO₂ Trapping Using Alkynyl Indoles

Myoglobin‐Catalyzed C−H Functionalization of Unprotected Indoles

Role of Indole Scaffolds as Pharmacophores in the Development of Anti-Lung Cancer Agents

Contact Info

Product

Resources

About

Electrophilic Substitution Reactions of Indoles

Cited by 49 publications

References 365 publications

Organocatalyzed CO2 Trapping Using Alkynyl Indoles

Organocatalyzed CO2 Trapping Using Alkynyl Indoles

Myoglobin‐Catalyzed C−H Functionalization of Unprotected Indoles

Role of Indole Scaffolds as Pharmacophores in the Development of Anti-Lung Cancer Agents

Contact Info

Product

Resources

About

Organocatalyzed CO₂ Trapping Using Alkynyl Indoles

Organocatalyzed CO₂ Trapping Using Alkynyl Indoles