2022
DOI: 10.3762/bjoc.18.33
|View full text |Cite
|
Sign up to set email alerts
|

Regioselectivity of the SEAr-based cyclizations and SEAr-terminated annulations of 3,5-unsubstituted, 4-substituted indoles

Abstract: Indole-3,4- and 4,5-fused carbo- and heterocycles are ubiquitous in bioactive natural products and pharmaceuticals, and hence, a variety of synthetic approaches toward such compounds have been developed. Among these, cyclization and annulation of 3,5-unsubstituted, 4-substituted indoles involving an electrophilic aromatic substitution (SEAr) as the ring closure are particularly attractive, because they avoid the use of 3,4- or 4,5-difunctionalized indoles as starting materials. However, since 3,5-unsubstituted… Show more

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...
1

Citation Types

0
2
0

Year Published

2023
2023
2024
2024

Publication Types

Select...
2

Relationship

0
2

Authors

Journals

citations
Cited by 2 publications
(2 citation statements)
references
References 25 publications
0
2
0
Order By: Relevance
“…The ring-opening of epoxides, whether in simple transformations or in cascade reactions, constitutes a powerful tool for the elaboration of a diverse class of acyclic and (poly)cyclic compounds—ranging from simple primary alcohols to complex natural products. 8 Nucleophilic aromatic substitution (S N Ar) is another hallmark reaction widely used for arene functionalization. 9 Notably, S N Ar is the second most frequently-used transformation after amide bond formation reaction in medicinal chemistry.…”
Section: Introductionmentioning
confidence: 99%
“…The ring-opening of epoxides, whether in simple transformations or in cascade reactions, constitutes a powerful tool for the elaboration of a diverse class of acyclic and (poly)cyclic compounds—ranging from simple primary alcohols to complex natural products. 8 Nucleophilic aromatic substitution (S N Ar) is another hallmark reaction widely used for arene functionalization. 9 Notably, S N Ar is the second most frequently-used transformation after amide bond formation reaction in medicinal chemistry.…”
Section: Introductionmentioning
confidence: 99%
“…Epoxide-opening cyclization represents another highly useful reaction that enables the construction of stereogenic sp 3 -carbon-bearing carbo- and heterocycles, often under full regio- and stereo-control. 4 In conjunction with our program directed toward the development of new cyclization strategies making use of intramolecular epoxide-opening reactions, 5 in 2020, we disclosed a base-mediated exo -selective epoxide-opening cyclization/intramolecular S N Ar cascade of ortho -fluorobenzenesulfonamide-tethered epoxides (Scheme 1A). 6 In the same year, Ma and co-workers synthesized 1-(arylamino)propan-2-ols via the reaction of EWG-substituted arylsulfonyl amides with terminal epoxides (Scheme 1B).…”
mentioning
confidence: 99%