La(NO&lt;sub&gt;3&lt;/sub&gt;)&lt;sub&gt;3&lt;/sub&gt;.6H&lt;sub&gt;2&lt;/sub&gt;O Catalyzed One-pot Highly Diastereoselective Synthesis of Functionalized Piperidines

Mousavi, Maryam; Aboonajmi, Jasem; Maghsoodlou, Malek Taher; Hazeri, Nourallah; Habibi‐Khorassani, Sayyed Mostafa; Safarzaei, Mohyeddin

doi:10.2174/1570178611310030005

Cited by 22 publications

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“…Moreover, it can be used as an animal feed ingredient to satisfy the potassium requirements of farm animals such as broiler breeders. 54,55 Having these points in mind, and as part of our continued interest in the development of multicomponent reactions and new methods for the synthesis of different compounds, [56][57][58][59][60][61][62][63][64][65] and as a continuation of our previous work in cyclocondensation reaction for synthesizing of cyclohexenone derivatives, [66][67][68] herein we report a new method for environmentally benign synthesis of (1S,6R)/ (1R,6S)-2-oxo-N,4,6-triarylcyclohex-3-enecarboxamides via a one-pot three-component Claisen-Schmidt condensation and Michael reaction of acetophenone, aromatic aldehydes, and acetoacetanilide in the presence of 10 mol% of K 2 CO 3 as a cost-effective and efficient catalyst in H 2 O/EtOH as a green solvent system at room temperature (Scheme 1).…”

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confidence: 99%

Claisen–Schmidt condensation: Synthesis of (1S,6R)/(1R,6S)‐2‐oxo‐N,4,6‐triarylcyclohex‐3‐enecarboxamide derivatives with different substituents in H₂O/EtOH

Mousavi

2016

Chirality

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A simple, green, and direct three-component condensation of acetophenone, aromatic aldehydes with 3-oxo-N-phenylbutanamide (acetoacetanilide) to generate some novel (1S,6R)/(1R,6S)-2-oxo-N,4,6-triarylcyclohex-3-enecarboxamide derivatives was carried out over K CO (10 mol%) with high efficiency in water/ethanol as green solvent at room temperature. This protocol proceeded via Claisen-Schmidt condensation and Michael addition. The present methodology offers several advantages, such as short reaction time, high yield, more readily available and inexpensive materials, more environmentally friendly, no need for column chromatography, simple work-up procedure, and the absence of volatile and hazardous organic solvents.

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Section: Introductionmentioning

confidence: 99%

Claisen–Schmidt condensation: Synthesis of (1S,6R)/(1R,6S)‐2‐oxo‐N,4,6‐triarylcyclohex‐3‐enecarboxamide derivatives with different substituents in H₂O/EtOH

Mousavi

2016

Chirality

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ChemInform Abstract: La(NO₃)₃·6H₂O Catalyzed One‐Pot Highly Diastereoselective Synthesis of Functionalized Piperidines.

et al. 2013

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Kinetics and related studies of the formation of 2,3‐dihydroquinazolin‐4(1H)‐ones in the presence of different benzaldehyde derivatives

Mostafa

Shahraki

Habibi‐Khorassani

2017

J of Physical Organic Chem

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The kinetics and activation parameters for the reaction between 2-aminobenzamide and some benzaldehyde derivatives in the presence of formic acid have been reported and discussed. A linear plot of lnk vs l/T showed that the reactions obey the Arrhenius equation. Both the Arrhenius and the Eyring equations were used to calculate the activation energy. The effect of nitro groups was studied on different positions of benzaldehyde. For all substituents, the reactions followed second-order kinetics, and the partial orders of reactions were recognized with respect to each reactant. Comparisons between the magnitudes of ΔH ‡ and TΔS ‡ showed that the reactions were enthalpy controlled.The validity of the isokinetic relationship and the compensation effect was tested, and the isokinetic temperature (β) was obtained. A linear enthalpyentropy plot (ΔH ‡ versusΔS ‡ ) showed that the compensation effect is established, and this process occurs via a same mechanism across a series of reactions. From the Van't Hoff and Exner's plots, the isokinetic temperature was obtained.

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La(NO<sub>3</sub>)<sub>3</sub>.6H<sub>2</sub>O Catalyzed One-pot Highly Diastereoselective Synthesis of Functionalized Piperidines

Cited by 22 publications

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Claisen–Schmidt condensation: Synthesis of (1S,6R)/(1R,6S)‐2‐oxo‐N,4,6‐triarylcyclohex‐3‐enecarboxamide derivatives with different substituents in H₂O/EtOH

Claisen–Schmidt condensation: Synthesis of (1S,6R)/(1R,6S)‐2‐oxo‐N,4,6‐triarylcyclohex‐3‐enecarboxamide derivatives with different substituents in H₂O/EtOH

ChemInform Abstract: La(NO₃)₃·6H₂O Catalyzed One‐Pot Highly Diastereoselective Synthesis of Functionalized Piperidines.

Kinetics and related studies of the formation of 2,3‐dihydroquinazolin‐4(1H)‐ones in the presence of different benzaldehyde derivatives

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La(NO<sub>3</sub>)<sub>3</sub>.6H<sub>2</sub>O Catalyzed One-pot Highly Diastereoselective Synthesis of Functionalized Piperidines

Cited by 22 publications

References 0 publications

Claisen–Schmidt condensation: Synthesis of (1S,6R)/(1R,6S)‐2‐oxo‐N,4,6‐triarylcyclohex‐3‐enecarboxamide derivatives with different substituents in H2O/EtOH

Claisen–Schmidt condensation: Synthesis of (1S,6R)/(1R,6S)‐2‐oxo‐N,4,6‐triarylcyclohex‐3‐enecarboxamide derivatives with different substituents in H2O/EtOH

ChemInform Abstract: La(NO3)3·6H2O Catalyzed One‐Pot Highly Diastereoselective Synthesis of Functionalized Piperidines.

Kinetics and related studies of the formation of 2,3‐dihydroquinazolin‐4(1H)‐ones in the presence of different benzaldehyde derivatives

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Claisen–Schmidt condensation: Synthesis of (1S,6R)/(1R,6S)‐2‐oxo‐N,4,6‐triarylcyclohex‐3‐enecarboxamide derivatives with different substituents in H₂O/EtOH

Claisen–Schmidt condensation: Synthesis of (1S,6R)/(1R,6S)‐2‐oxo‐N,4,6‐triarylcyclohex‐3‐enecarboxamide derivatives with different substituents in H₂O/EtOH

ChemInform Abstract: La(NO₃)₃·6H₂O Catalyzed One‐Pot Highly Diastereoselective Synthesis of Functionalized Piperidines.