Novel synthetic route to 1,4-dihydropyridines from β-amino acrylates by using titanium(IV) chloride under facile conditions

Sirijindalert, Thirawat; Hansuthirakul, Kunlayanee; Rashatasakhon, Paitoon; Sukwattanasinitt, Mongkol; Ajavakom, Anawat

doi:10.1016/j.tet.2010.04.102

Cited by 48 publications

(45 citation statements)

References 21 publications

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“…The addition of one more 69 to 70 led to formation of intermediates 71, and the intramolecular elimination cyclization of 71 provided products 72 (Scheme 28). 45 Owing to the excellent reactivity and diverse availability of enaminones, many diversity oriented, enaminone-based synthesis of 1,4-DHPs have been reported by using either new 1,3-dicarbonyl substrates or enaminones/b-enamino esters. For example, enaminone 73 has been found as an ideal reaction partner of isatin and cyclic 1,3-diketones to yield spiro-fused 1,4-DHPs 74 in refluxing water with the catalysis of Brønsted acid p-TSA (Eq 1 in Scheme 29), 46 while enaminone 75 with the coumarin backbone has been reported as practical precursor for the synthesis of highly functionalized 1,4-DHPs 76 employing (¡) lactic acid and ethyl lactate as catalyst and green solvent, respectively (Eq 2 in Scheme 29).…”

Section: Multicomponent Synthesis Of 14-dhps Using Ammonia As Amino mentioning

confidence: 99%

Recent advances in new multicomponent synthesis of structurally diversified 1,4-dihydropyridines

2012

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1,4-Dihydropyridines (DHPs) are one of the most important classes of heterocyclic compounds as privileged pharmacophores. They are therefore attractive synthetic targets of organic chemistry. Multicomponent reactions (MCRs) are the most efficient strategies for the synthesis of 1,4-DHPs in terms of providing both sufficient structural diversity and numbers for compound libraries. Following the classical multicomponent synthesis of 1,4-DHPs by the Hantzsch reaction, chemists have developed a large number of new MCRs to access 1,4-DHPs with significantly extended structural diversity, which is pivotal for the process of discovering new lead compounds and drugs of 1,4-DHPs. The advances on the synthesis of structurally diversified 1,4-DHPs through new MCRs beyond the classical Hantzsch reaction is reviewed.

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Section: Multicomponent Synthesis Of 14-dhps Using Ammonia As Amino mentioning

confidence: 99%

Recent advances in new multicomponent synthesis of structurally diversified 1,4-dihydropyridines

2012

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“…This reaction and its regioselectivity will be examined further in our laboratory. Postulated intermediate 8 , which leads to 1,2‐dihydropyridines 5′ and trisubstituted benzene 6 a , was not detected, whereas intermediate structure 7 , previously suggested in the synthesis of 1,4‐dihydropyridines by the Lewis acid catalyzed dimerization of enamino esters, has been proven in our work by its isolation in several cases (see below).…”

Section: Resultsmentioning

confidence: 99%

Silica Gel as a Promoter of Sequential Aza‐Michael/Michael Reactions of Amines and Propiolic Esters: Solvent‐ and Metal‐Free Synthesis of Polyfunctionalized Conjugated Dienes

Aleksić

Stojanović

Baranac‐Stojanović

2018

Chemistry An Asian Journal

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We present an efficient, simple, metal- and solvent-free silica-gel-promoted synthesis of functionalized conjugated dienes by sequential aza-Michael/Michael reactions by starting from commercially available primary amines and propiolic esters. The scope and usefulness of the method is demonstrated for 31 examples, including a range of propiolic esters, aliphatic amines, and differently substituted aromatic amines. For aliphatic amines, the products were obtained within 0.5 to 4 h in 52 to 85 % yield, compared with 3.5 to 22 h under classical solution-phase synthesis, which proceeds with similar or lower yields. The method was found to be particularly useful for weakly nucleophilic aromatic amines, which provided products in 21 to 73 % yield over 2.5 to 9.5 h compared with yields of 0 to 49 % over 1 to 6 d under standard solution-phase conditions, and for more hydrophobic esters that gave products in yields of 47 to 79 % over 1 to 3 h compared with 0 to 45 % over 4 to 114 h in solvent.

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“…Ajavakom, et al 63 have screened several Lewis acid catalysts such as BF 3 $OEt 2 , AlCl 3 , and TiCl 4 on b-amino acrylates 154, for the synthesis of 1,4-dihydropyridine 155 (Scheme 54). The yield of product 155 obtained from these initial screening of the Lewis acid catalyst were not satisfactory, which may be likely due to the decomposition of the acetal group in b-amino acrylate 154 under acidic conditions.…”

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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Novel synthetic route to 1,4-dihydropyridines from β-amino acrylates by using titanium(IV) chloride under facile conditions

Cited by 48 publications

References 21 publications

Recent advances in new multicomponent synthesis of structurally diversified 1,4-dihydropyridines

Recent advances in new multicomponent synthesis of structurally diversified 1,4-dihydropyridines

Silica Gel as a Promoter of Sequential Aza‐Michael/Michael Reactions of Amines and Propiolic Esters: Solvent‐ and Metal‐Free Synthesis of Polyfunctionalized Conjugated Dienes

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

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