Selective synthesis of 1,4,5-trisubstituted imidazoles from α-imino ketones prepared by N-heterocyclic-carbene-catalyzed aroylation

Takashima, Ryo; Tsunekawa, Kaoru; Shinozaki, Maki; Suzuki, Yumiko

doi:10.1016/j.tet.2018.03.048

Cited by 11 publications

(6 citation statements)

References 37 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Traditionally, C ‐acylimines are made from readily available, less expensive glyoxals and amines by water removal by a simple mixing under different conditions [1] . Subsequently, a few other methods were also developed, for example, NHC‐catalyzed aroylation of aromatic aldehydes with imidoylchlorides [2] and a nitrosobenzene mediated C−C bond cleavage reaction with LHMDS [3] etc. However, In this small review, we limit ourselves to showcasing the synthetic applications of C ‐acylimines, but not their synthesis.…”

Section: Introductionmentioning

confidence: 99%

Synthetic Applications of Ambiphilic C‐acylimines in Organic Synthesis

2022

View full text Add to dashboard Cite

C‐acylimines are generally obtained through condensation/dehydration of simple and readily available glyoxals and amines. The structure resembles naturally occurring biological substances due to the presence of the imino group (−N=C−). Chemically, C‐acylimines exhibit ambiphilic reactivity, and hence, their synthetic chemistry becomes more attractive and viable for the synthesis of various aza‐cyclic/heterocyclic compounds, including their asymmetric counterpart. Therefore, many synthetic methodologies were developed from these readily preparable C‐acylimines. Surprisingly, there is no account/review available on this specific topic. Hence we present here an account of all the synthetic endeavours developed from C‐acylimines to synthesize small molecules and complex systems using various strategies.

show abstract

Section: Introductionmentioning

confidence: 99%

Synthetic Applications of Ambiphilic C‐acylimines in Organic Synthesis

2022

View full text Add to dashboard Cite

show abstract

“…Imidazole derivatives are an important class of heterocyclic compounds [19,20] that exhibiting biological and pharmacological properties [21][22][23]. Also, oxazocine heterocyclic compounds are active compounds against CNS disorders and are used for the treatment of pain and/or inflammation [24].…”

Section: Introductionmentioning

confidence: 99%

One-Pot Synthesis of Novel Furochromone and Oxazocine Derivatives as Promising Antitumor Agents with Their Molecular Docking Studies

Borik

2020

Journal of Chemistry

View full text Add to dashboard Cite

One-pot efficient synthesis of novel chromone derivatives 4a–h and that of 5a–h were described in a simple method via four-component reaction between furochromone carbaldehyde, amine, isocyanate derivatives, and benzoic acid derivatives or nicotinic acid, respectively. Also, oxazocine derivatives 7a, b were prepared via reaction of visnagine carbaldehyde, ethyl acetoacetate and isocyanate derivatives 2a, b. The obtained derivatives of novel furochromone and oxazocine derivatives were evaluated as promising antitumor agents against panel of two human cell lines, hepatocellular carcinoma (HEPG2) and breast carcinoma (MCF7). The antitumor results suggested that furochromone derivatives 5a–h have activity against MCF7 in comparison with doxorubicin as the standard drug. Furthermore, the molecular docking studies of these novel derivatives of furochromone and oxazocine showed good agreement with the biological results when their binding pattern and affinity towards the active site of EGFR was investigate.

show abstract

“…The traditional method of synthesizing α-imino ketone relied on the condensation reaction under different conditions with diketone and amine as raw materials (Scheme a) . Subsequently, Suzuki and co-workers developed an interesting way for obtaining α-imino ketones with imidoyl chlorides and aromatic aldehydes as substrate via N -heterocycle carbene-catalyzed aroylation (Scheme b) . In addition, Yamamoto and co-workers found that α-ketone imines could be achieved via a nitrosobenzene-mediated C–C bond cleavage reaction (Scheme c) .…”

mentioning

confidence: 99%

“…3 Subsequently, Suzuki and co-workers developed an interesting way for obtaining α-imino ketones with imidoyl chlorides and aromatic aldehydes as substrate via N-heterocycle carbene-catalyzed aroylation (Scheme 1b). 4 In addition, Yamamoto and co-workers found that α-ketone imines could be achieved via a nitrosobenzene-mediated C−C bond cleavage reaction (Scheme 1c). 5 According to the previous methods, the reactions were restricted to special substrates or harsh reaction conditions.…”

mentioning

confidence: 99%

Preparation and Application of α-Imino Ketones through One-Pot Tandem Reactions Based on Heyns Rearrangement

Zhang

Deng

et al. 2021

Org. Lett.

View full text Add to dashboard Cite

α-Imino ketone is a useful building block for the preparation of α-amino ketones and α-amino alcohols. However, its preparation has been seldomly seen. Herein, a metal-free and operationally simple strategy has been developed to generate αimino ketones with high regioselectivity. Meanwhile, the method allowed for the preparation of various N,O-ketals with high regioselectivities and diastereoselectivities through cascade reactions in one pot.

show abstract

Selective synthesis of 1,4,5-trisubstituted imidazoles from α-imino ketones prepared by N-heterocyclic-carbene-catalyzed aroylation

Cited by 11 publications

References 37 publications

Synthetic Applications of Ambiphilic C‐acylimines in Organic Synthesis

Synthetic Applications of Ambiphilic C‐acylimines in Organic Synthesis

One-Pot Synthesis of Novel Furochromone and Oxazocine Derivatives as Promising Antitumor Agents with Their Molecular Docking Studies

Preparation and Application of α-Imino Ketones through One-Pot Tandem Reactions Based on Heyns Rearrangement

Contact Info

Product

Resources

About