Organocatalytic Asymmetric Transformations Involving the Cyclic Imine Moiety in Indole and Isoindole Related Heterocycles

Cheng, Dao‐Juan; Shao, Yan

doi:10.1002/adsc.201800345

Cited by 50 publications

(15 citation statements)

References 119 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Several natural and synthetic pharmaceutical compounds have the isoindole nucleus in their structures [185] . For this reason, many studies have been carried out on the synthesis and biological evaluation of these compounds [15,186] . The best way to prepare isoindole derivatives is through the Diels‐Alder cyclization.…”

Section: Introductionmentioning

confidence: 99%

“…[5] Indoles have been studied for over one hundred years and these studies delivered to the scientific community impressive advances in biological properties [6] and synthetic applications of this class of compounds. [7] Although less studied, its derivatives azaindole, [8] carbazole, [9] carboline, [10] indazole, [11] 3H-indole, [12] indoline, [13] indolizine, [14] isoindole, [15] and isoindoline [16] have gained prominence in organic synthesis, medicinal chemistry, materials science, and industry. Because of such an application, the synthesis of indole derivatives has been a subject of several approaches.…”

Section: Introductionmentioning

confidence: 99%

“…[185] For this reason, many studies have been carried out on the synthesis and biological evaluation of these compounds. [15,186] The best way to prepare isoindole derivatives is through the Diels-Alder cyclization. They are also prepared by using cyclization reactions starting from alkynes and nitrogen compounds.…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Recent Developments in the Cyclization of Alkynes and Nitrogen Compounds for the Synthesis of Indole Derivatives

Neto

Zeni

2021

Asian J Org Chem

View full text Add to dashboard Cite

This review is intended to highlight the most useful approaches for the synthesis of indole derivatives (azaindoles, carbazoles, carbolines, indazoles, 3H-indoles, indolines, indolizines, isoindoles, and isoindolines), which were described by using transition-metal catalyzed cyclization reactions of alkynes and nitrogen compounds. The methodologies carried out under metal-free conditions will also be illustrated herein. This review will cover the data published mostly in the past decade. Synthesis of 6-AzaindolesAzaindoles, although rare in nature, have attracted a significant attention because some synthetic structures containing this nucleus exhibit biological activities. [17] The synthetic methods describing the preparation of azaindoles are limited. Usually their synthesis was achieved from the cyclization reaction of substrates containing aminopyridines. [18] Transition Metal-Free Synthesis of 6-AzaindolesWe have nominated two methodologies for the preparation of 6-azaindoles, which were developed using alkynes and nitrogen compounds in a metal-free protocol. In the first, an electrophilic cyclization condition, using iodine as an electrophilic source, was applied to 2-(azidomethyl)-3-alkynyl-pyrroles in the preparation of 4-iodo-6-azaindoles 1 (Scheme 1, eq 1). [19] The second approach described the preparation of 2,5-disubstituted 6azaindoles 2 from base-catalyzed intramolecular cyclization of 2-(azidomethyl)-3-alkynyl-pyrroles (Scheme 1, eq 2). [20] 3. Synthesis of 7-Azaindoles Transition Metal-Catalyzed Synthesis of 7-Azaindoles Silver-Catalyzed Synthesis of 7-AzaindolesSilver-catalyzed cyclization reactions of alkynes constitute powerful strategies for the construction of heterocycles. In particular, the 7-azaindoles could be obtained by these approaches. A general method for the preparation of aryl-[a] Dr. J.

show abstract

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Recent Developments in the Cyclization of Alkynes and Nitrogen Compounds for the Synthesis of Indole Derivatives

Neto

Zeni

2021

Asian J Org Chem

View full text Add to dashboard Cite

show abstract

“…Efficient construction of functionalized five‐membered carbo‐ and heterocycles with a defined configuration has drawn tremendous interest from synthetic organic chemists due to their widespread occurrence in natural products and pharmacologically active molecules . Extensive efforts in this area have resulted in the development of a plethora of synthetic methods to prepare these cycles with multifarious molecular architectures.…”

Section: Introductionmentioning

confidence: 99%

Recent Advances in Phosphine‐Promoted (4 + 1) Annulation Reactions

Zhang

Zhou

2020

Eur J Org Chem

View full text Add to dashboard Cite

Over the past two decades, the nucleophilic phosphine catalysis has effected many powerful annulation reactions and emerged as an intriguing platform for the generation of highly functionalized carbo‐ and heterocycles. In addition to the well‐established (3 + 2) annulation, the phosphine‐promoted (4 + 1) annulation has received increasing attention and developed rapidly in recent years, which complements the (3 + 2) annulation and also provides an alternative approach to structurally diverse five‐membered carbo‐ and heterocycles. This minireview summarizes the recent advances in phosphine‐promoted (4 + 1) annulation reactions according to the type of substrates used in the annulations.

show abstract

“…[6] In this context, aza-Friedel-Crafts alkylation (aza-FCA) reactions with heteroarenes were well studied through chiral phosphoric acid (CPA) catalysis. [7][8][9][10] Particularly, the strategies involving cyclic ketimines are highly attractive as these could render target-orientated heterocyclic scaffolds containg a quaternary stereogenic centre. [11] Among the five-membered heterocyclic compounds, isoxazoline is an important scaffold that is found in various biologically active molecules and natural products.…”

mentioning

confidence: 99%

Enantioselective Aza‐Friedel‐Crafts Reaction of Heteroarenes with in situ Generated Isoxazolium Ions via Chiral Phosphoric Acid Catalysis

et al. 2021

View full text Add to dashboard Cite

An asymmetric organocatalytic aza-Friedel-Crafts reaction was developed to give the enantioenriched Δ 4 -isoxazoline scaffold bearing a quaternary-substituted stereogenic centre in goodto-excellent yields and enantioselectivity (50-99%, 55-> 99% ee). This protocol involves the in situ generated isoxazolium ions in the presence of a chiral phosphoric acid followed by the heteroarene addition through asymmetric counteranion-directed catalysis.

show abstract

Organocatalytic Asymmetric Transformations Involving the Cyclic Imine Moiety in Indole and Isoindole Related Heterocycles

Cited by 50 publications

References 119 publications

Recent Developments in the Cyclization of Alkynes and Nitrogen Compounds for the Synthesis of Indole Derivatives

Recent Developments in the Cyclization of Alkynes and Nitrogen Compounds for the Synthesis of Indole Derivatives

Recent Advances in Phosphine‐Promoted (4 + 1) Annulation Reactions

Enantioselective Aza‐Friedel‐Crafts Reaction of Heteroarenes with in situ Generated Isoxazolium Ions via Chiral Phosphoric Acid Catalysis

Contact Info

Product

Resources

About