Ceric Ammonium Nitrate (CAN) Catalyzes the One‐Pot Synthesis of Polyhydroquinoline via the Hantzsch Reaction.

Ko, Shengkai; Yao, Ching‐Fa

doi:10.1002/chin.200645146

Cited by 4 publications

(5 citation statements)

References 1 publication

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Recently, a series of new 4‐substituted‐1,4‐dihydropyridine derivatives was synthesized by using various substituted benzaldehydes, 1,3‐cyclohexanedione or 5,5‐dimethyl‐1,3‐cyclohexanedione, ethyl acetoacetate, and ammonium acetate under different reaction conditions . However, these 4‐substituted‐1,4‐dihydropyridine derivatives were all obtained as racemic mixtures, which have not been resolved.…”

Section: Introductionmentioning

confidence: 99%

“…The available Chiralpak AD‐H (AD) commercial column was investigated in this work in order to help elucidate aspects of the chiral resolution mechanism for asymmetric 1,4‐dihydropyridine compounds. Thirty 1,4‐dihydropyridine compounds, 1 , 2 , 3 , 4 , 5 , 6 , 7 , 8 , 9 , 10 , 11 , 12 , 13 , 14 , 15 , 16 , 17 , 18 , 19 , 20 , 21 , 22 , 23 , 24 , 25 , 26 , 27 , 28 , 29 , 30 , were synthesized and purified for this purpose in this current work by using the method pioneered by Ko and Yao (Fig. ).…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Enantiomeric Recognition of Racemic 4‐Aryl‐1,4‐dihydropyridine Derivatives via Chiralpak AD‐H Stationary Phases

Dai

Pittman

2012

Chirality

View full text Add to dashboard Cite

The chromatographic chiral resolution of two new series of racemic 4-substituted-1,4-dihydropyridine derivatives was studied on a commercial Chiralpak AD-H column. Analytes without 5,5-dimethyl substituents (1-15) are more efficiently resolved than analytes with 5,5-dimethyl groups (16-30). The AD-H column discriminated between enantiomers through both hydrogen bonding attractions and π-π interactions. This interpretation is in accord with plots of the logarithm of separation factors, log(α), versus σ (Hammett-Swain substituent parameter) and σ(+) (Brown substituent constant) plots. By elucidating the effects of the remote substituents on these chiral separations, it was shown that the influence of π-π interaction forces increase when steric bulk effects act to decrease the hydrogen bonding attractive forces on the AD-H column.

show abstract

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Enantiomeric Recognition of Racemic 4‐Aryl‐1,4‐dihydropyridine Derivatives via Chiralpak AD‐H Stationary Phases

Dai

Pittman

2012

Chirality

View full text Add to dashboard Cite

show abstract

“…However, most of these reactions were reported with new trends as one-pot multicomponent reactions (MCRs) in the last 10–15 years; these reactions were carried out with certain disadvantages like: longer reaction time, expensive catalyst, higher temperature and tedious workup procedure. Great diversity in MCRs [11–13], developed using various ionic liquids as various Lowry-Bronsted acids, with several advantages has been well documented [14–16]. The clinical significance of pyran, thiophene derivatives of 3-acetylcoumarine based on 1,4-DHPs was the concern that they were reported to have an equivalent cytotoxic effect as the standard CHS 828 against a breast cancer cell line [17].…”

Section: Introductionmentioning

confidence: 99%

Green approach for synthesis of bioactive Hantzsch 1,4-dihydropyridine derivatives based on thiophene moiety via multicomponent reaction

2017

View full text Add to dashboard Cite

A novel green and efficient one-pot multicomponent reaction of dihydropyridine derivatives was reported as having good to excellent yield. In the presence of the catalyst ceric ammonium nitrate (CAN), different 1,3-diones and same starting materials as 5-bromothiophene-2-carboxaldehyde and ammonium acetate were used at room temperature under solvent-free condition for the Hantzsch pyridine synthesis within a short period of time. All compounds were evaluated for their in vitro antibacterial and antifungal activity and, interestingly, we found that 5(b–f) show excellent activity compared with Ampicillin, whereas only the 5e compound shows excellent antifungal activity against Candida albicans compared with griseofulvin. The cytotoxicity of all compounds has been assessed against breast tumour cell lines (BT-549), but no activity was found. The X-ray structure of one such compound, 5a, viewed as a colourless block crystal, corresponded accurately to a primitive monoclinic cell.

show abstract

“…A series of new 4‐aryl‐1,4‐dihydropyridines was recently synthesized by using substituted benzaldehyde, 1,3‐cyclohexanedione or 5,5‐dimethyl‐1,3‐cyclohexanedione, ethyl acetoacetate, and ammonium acetate under different reaction conditions . We expanded the number of 4‐aryl‐1,4‐dihydropyridines prepared by this pathway and then demonstrated their resolution on a commercial Chiralpak AD‐H (25‐cm) column for the first time .…”

Section: Introductionmentioning

confidence: 99%

Enantiomeric Separation of Racemic 4‐Aryl‐1,4‐Dihydropyridines and 4‐Aryl‐1,2,3,4‐Tetrahydropyrimidines on a Chiral Tetraproline Stationary Phase

Dai

Pittman

2013

Chirality

View full text Add to dashboard Cite

The chromatographic chiral resolution of 4-aryl-1,4-dihydropyridines (1-32), 4-aryl-2-thioxo-1,2,3,4-tetrahydropyrimidines (33-38), and 4-aryl-2-oxo-1,2,3,4-tetrahydropyrimidines (39-41) was studied on a tetraproline-immobilized chiral column synthesized in our lab. This tetraproline chiral stationary phase can resolve most of these compounds. The 4-aryl-2-thioxo-1,2,3,4-tetrahydropyrimidines (33-38) and 4-aryl-2-oxo-1,2,3,4-tetrahydropyrimidines (39-41) were more efficiently resolved than the racemic 4-aryl-1,4-dihydropyridines on the tetraproline chiralstationary phase. Analytes with 5,5-dimethyl groups (39-41) were less efficiently resolved than analytes without 5,5-dimethyl substituents (1-16). The 4-aryl-2-oxo-1,2,3,4-tetrahydropyrimidines (39-41) without a sulfur atom were much more efficiently resolved than 4-aryl-2-thioxo-1,2,3,4-tetrahydropyrimidines (33-38). No obvious electronic effects on the resolution of any of these analytes (1-41) were observed on the tetraproline chiral stationary phase. The tetraproline chiral stationary phase separated enantiomers mainly via hydrogen bonding interactions.

show abstract

Ceric Ammonium Nitrate (CAN) Catalyzes the One‐Pot Synthesis of Polyhydroquinoline via the Hantzsch Reaction.

Abstract: ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.

Cited by 4 publications

References 1 publication

Enantiomeric Recognition of Racemic 4‐Aryl‐1,4‐dihydropyridine Derivatives via Chiralpak AD‐H Stationary Phases

Enantiomeric Recognition of Racemic 4‐Aryl‐1,4‐dihydropyridine Derivatives via Chiralpak AD‐H Stationary Phases

Green approach for synthesis of bioactive Hantzsch 1,4-dihydropyridine derivatives based on thiophene moiety via multicomponent reaction

Enantiomeric Separation of Racemic 4‐Aryl‐1,4‐Dihydropyridines and 4‐Aryl‐1,2,3,4‐Tetrahydropyrimidines on a Chiral Tetraproline Stationary Phase

Contact Info

Product

Resources

About