General Transition Metal-Free Synthesis of NH-Pyrroles from Secondary Alcohols and 2-Aminoalcohols

Krasniqi, Besir; Geerts, Kayle; Dehaen, Wim

doi:10.1021/acs.joc.8b03215

Cited by 16 publications

(10 citation statements)

References 47 publications

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“…Nitrogen-containing heterocycles (such as pyrroles and pyridines) are one of the most prevalent compounds in numerous natural products, potent pharmaceutical drugs, and various kinds of functional materials. In the past decades, diverse synthetic approaches toward pyrroles and pyridines have been developed . However, versatile and flexible methodologies to construct pyrroles or pyridines using fundamental building blocks, which are readily accessible and stable enough to be stored for a long time, are still needed.…”

Section: Introductionmentioning

confidence: 99%

Syntheses of Pyrroles, Pyridines, and Ketonitriles via Catalytic Carbopalladation of Dinitriles

Yao

et al. 2019

J. Org. Chem.

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The first example of the Pd-catalyzed addition of organoboron reagents to dinitriles, as an efficient means of preparing 2,5-diarylpyrroles and 2,6-diarylpyridines, has been discussed here. Furthermore, the highly selective carbopalladation of dinitriles with organoboron reagents to give long-chain ketonitriles has been developed as well. Based on the broad scope of substrates, excellent functional group tolerance, and use of commercially available substrates, the Pd-catalyzed addition reaction of arylboronic acid and dinitriles is expected to be significant in future synthetic procedures.

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Section: Introductionmentioning

confidence: 99%

Syntheses of Pyrroles, Pyridines, and Ketonitriles via Catalytic Carbopalladation of Dinitriles

Yao

et al. 2019

J. Org. Chem.

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“…In contrast to the presented method Dehaen and colleagues [16] reported, in 2019, metal-free interaction of secondary alcohols 41 and 2-aminoalcohols 45, which leads to NH-pyrroles 47 in good yields (Scheme 13).…”

Section: Synthesis With Aminesmentioning

confidence: 85%

Recent Advances for the Synthesis of N‐Unsubstituted Pyrroles

et al. 2021

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Pyrroles are an interesting class of heterocyclic compounds due to their widespread use both in medical chemistry and in the chemistry of new materials. Search and development of new effective methods for the synthesis of the pyrrole ring is an urgent task. Along with this, the systematization of already known synthesis methods is an equally important task. Herein, we focused on the results of the synthesis of NH‐pyrroles that have been obtained since 2015.

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“…Dehaen et al 108 described a new one-pot metal-free method for the synthesis of various substituted NH-pyrroles, including 4,5,6,7-tetrahydroindoles from readily available building blocks, such as secondary alcohols and 2-…”

Section: Scheme 62 Synthesis Of N-(2-hydroxyethyl)cycloalkane-fused P...mentioning

confidence: 99%

Recent Advances in the Synthesis of Indoles with Partially Hydrogenated Benzene Ring (Tetrahydroindoles)

Mamedov,

Zhukova

2023

Synthesis

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In this review, a fragmentary analysis of 4,5,6,7-tetrahydroindoles was performed and, on its basis, the existing methods of their synthesis published over the past 15 years have been summarized, and analyzed, as well as, if necessary, an analysis of earlier works is carried out. The proposed reaction mechanism is considered, as well as factors that significantly influence the course of the process. Among such factors: temperature, type and content of the catalyst, promoting additives, method of the process, etc. Particular attention is paid to fundamentally new methods that make it possible to synthesize various derivatives of the mentioned heterocyclic systems from available and cheap reagents, and in some cases under environmentally benign conditions.1 Introduction2 Intramolecular Reactions Leading To Tetrahydroindoles2.1 Ring Closure Reactions with N–C2 Bond Formation (a)2.2 Ring Closure Reactions with C2–C3 Bond Formation (b)2.3 Ring Closure Reactions with C3–C3a Bond Formation (c)2.4 Ring Closure Reactions with C7a–N Bond Formation (e)2.5 Ring Closure Reactions with C4–C5 Bond Formation (g)2.6 Ring Closure Reactions with C3a–C4 Bond Formation (h)3 Intermolecular Reactions Leading To Tetrahydroindoles3.1 Ring Closure Reactions with N–C2 + C3–C3a Bond Formation (ac)3.2 Ring Closure reactions with N–C2 + C7a–N Bond Formation (ae)3.3 Ring Closure reactions with C3–C3a + C7a–N Bond formation (ce)3.4 Ring Closure Reactions with N–C2, C3–C3a, and C7a–N Bond Formation (ace)4 Recovery Processes (Hydrogenation) of Indoles and Oxidation of Perhydroindoles in the Synthesis of 4,5,6,7-Tetrahydroindoles5 Conclusion

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General Transition Metal-Free Synthesis of NH-Pyrroles from Secondary Alcohols and 2-Aminoalcohols

Cited by 16 publications

References 47 publications

Syntheses of Pyrroles, Pyridines, and Ketonitriles via Catalytic Carbopalladation of Dinitriles

Syntheses of Pyrroles, Pyridines, and Ketonitriles via Catalytic Carbopalladation of Dinitriles

Recent Advances for the Synthesis of N‐Unsubstituted Pyrroles

Recent Advances in the Synthesis of Indoles with Partially Hydrogenated Benzene Ring (Tetrahydroindoles)

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