Metal-free Brønsted acids catalyzed synthesis of functional 1,4-dihydropyridines

Moreau, J.; Duboc, Agathe; Hubert, Claudie; Hurvois, Jean‐Pierre; Renaud, Jean‐Luc

doi:10.1016/j.tetlet.2007.10.040

Cited by 59 publications

(29 citation statements)

References 29 publications

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“…Renaud, et al 52 has developed Brønsted acid 132 catalyzed addition of b-enaminoacrylates 131a-d to a,b-unsaturated aldehydes 56a, 56c and 56d-h to afford the corresponding Nsubstituted 1,4-dihydropyridines 133a-m in 31-89% yields (Scheme 42).…”

Section: Scheme 44mentioning

confidence: 99%

Synthesis, utility and medicinal importance of 1,2- & 1,4-dihydropyridines

2017

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Dihydropyridine (DHP) is among the most beneficial scaffolds that have revolutionised pharmaceutical research with unprecedented biological properties. Over the years, metamorphosis of easily accessible 1,2-and 1,4-dihydropyridine (1,4-DHP) intermediates by synthetic chemists has generated several drug molecules and natural products such as alkaloids. The 1,4-dihydropyridine (1,4-DHP) moiety itself is the main fulcrum of several approved drugs. The present review aims to collate the literature of 1,2-and the 1,4-DHPs relevant to synthetic and medicinal chemists. We will describe various methodologies that have been used for the synthesis of this class of compounds, including the strategies which can furnish enantiopure DHPs, either by asymmetric synthesis or by chiral resolution.We will also elaborate the significance of DHPs towards the synthesis of natural products of medicinal merit.

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Section: Scheme 44mentioning

confidence: 99%

Synthesis, utility and medicinal importance of 1,2- & 1,4-dihydropyridines

2017

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“…The substituted dihydropyridines were obtained in moderate to good yields under mild conditions. 3 (B) Hong et al studied a series of homologous unsaturated aldehydes which were then reacted with L-proline in acetonitrile to afford the corresponding adducts. The reaction of 3-methyl-2-butenal with L-proline afforded a diene adduct in 82% yield via formal [4+2] cycloaddition.…”

Section: Abstractsmentioning

confidence: 99%

“…2 Various examples of the use of 3-methyl-2-butenal are found in the literature. This reagent has been explored for the preparation of 1,4-dihydropiridines, 3 diene adducts, 4 pyranonaphthoquinones, 5 nitropentanal pyrrole, 6 cyclization precursors, 7 and 2H-chromenes. 9…”

Section: Introductionmentioning

confidence: 99%

3-Methyl-2-Butenal

Ventura¹

2010

Synlett

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This feature focuses on a reagent chosen by a postgraduate, highlighting the uses and preparation of the reagent in current research 3-Methyl-2-Butenal Compiled by Claiton Pires VenturaClaiton Pires Ventura was born in Minas Gerais, Brazil in 1978. He received his B.Sc. degree in pharmacy from the Universidade Federal de Minas Gerais in 2001 and his M.Sc. in pharmacy from the same university in 2003. He is currently working toward his Ph.D. under the supervision of Professor Rosemeire Brondi Alves. His research interests focus on the synthesis of pterocarpans from 2H-chromenes.

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“…9 However, there have been only a few reports on the catalytic enantioselective synthesis of 1,4-DHP. 10,11 These methods can be classified into two synthetic pathways, as shown in Scheme 1.…”

Section: 4-dihydropyridinesmentioning

confidence: 99%

“…In these cases, the removal of an electron-withdrawing substituent or introduction of an electron-donating group led to a decrease in enantioselectivity (entries 5 and 6). In addition, we examined the reaction of 3a with b-enamino esters 2g-k with different N-substituents (entries [10][11][12][13][14]. b-Enamino ester 2g and 2h with a para-chlorophenyl group on nitrogen led to a decrease in enantioselectivity (entries 10 and 11).…”

Section: Figure 1 Structures Of Thiourea Catalysts Employedmentioning

confidence: 99%

Brønsted Acid-Thiourea Co-catalysis: Asymmetric Synthesis of Functionalized 1,4-Dihydropyridines from β-Enamino Esters and α,β-Unsaturated Aldehydes

Yoshida¹,

Inokuma²,

Takasu³

et al. 2010

Synlett

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LETTER 1865Brønsted Acid-Thiourea Co-catalysis: Asymmetric Synthesis of Functionalized 1,4-Dihydropyridines from b-Enamino Esters and a,b-Unsaturated Aldehydes A s y m m e t r i c S y n t h e s i s o f F u n c t i o n a l i z e d 1 , 4 -D i h y d r o p y r i d i n e sAbstract: A Brønsted acid and a novel thiourea derivative co-catalyze the addition of b-enamino esters to a,b-unsaturated aldehydes leading to functionalized 1,4-dihydropyridines with moderate to good enantioselectivity. A regioselective synthesis of 1,2-dihydropyridines from a,b-unsaturated aldehydes is also described.

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Metal-free Brønsted acids catalyzed synthesis of functional 1,4-dihydropyridines

Cited by 59 publications

References 29 publications

Synthesis, utility and medicinal importance of 1,2- & 1,4-dihydropyridines

Synthesis, utility and medicinal importance of 1,2- & 1,4-dihydropyridines

3-Methyl-2-Butenal

Brønsted Acid-Thiourea Co-catalysis: Asymmetric Synthesis of Functionalized 1,4-Dihydropyridines from β-Enamino Esters and α,β-Unsaturated Aldehydes

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Metal-free Brønsted acids catalyzed synthesis of functional 1,4-dihydropyridines

Cited by 59 publications

References 29 publications

Synthesis, utility and medicinal importance of 1,2- & 1,4-dihydropyridines

Synthesis, utility and medicinal importance of 1,2- & 1,4-dihydropyridines

3-Methyl-2-Butenal

Brønsted Acid-Thiourea Co-catalysis: Asymmetric Synthesis of Function­alized 1,4-Dihydropyridines from β-Enamino Esters and α,β-Unsaturated ­Aldehydes

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Brønsted Acid-Thiourea Co-catalysis: Asymmetric Synthesis of Functionalized 1,4-Dihydropyridines from β-Enamino Esters and α,β-Unsaturated Aldehydes