Phenylboronic acid as a mild and efficient catalyst for Biginelli reaction

Debache, Abdelmadjid; Boumoud, Boudjemaa; Amimour, Mouna; Belfaitah, Ali; Rhouati, Salah; Carboni, Bertrand

doi:10.1016/j.tetlet.2006.06.015

Cited by 107 publications

(40 citation statements)

References 31 publications

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“…For example, imine hydrolysis [50], epoxide ring opening [51], the Biginelli reaction [52], and dipolar cycloaddition [53] have already been performed under boronic acid catalysis. In 2008, Whiting et al reported a catalytic aldol reaction and condensation through in situ boron ate complex enolate generation in water (Scheme 17) [54].…”

Section: Other B(iii)-catalyzed Reactionsmentioning

confidence: 99%

Boronic Acid-Catalyzed Reactions of Carboxylic Acids

Ishihara

2015

Topics in Organometallic Chemistry

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Section: Other B(iii)-catalyzed Reactionsmentioning

confidence: 99%

Boronic Acid-Catalyzed Reactions of Carboxylic Acids

Ishihara

2015

Topics in Organometallic Chemistry

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“…The major drawbacks associated with this protocol are the use of strong acid as well as the low yields in the case of substituted aromatic and aliphatic aldehydes. To enhance the efficiency of the Biginelli reaction, various catalysts and reaction conditions have been studied including classical conditions with ultrasound [23] [36], PhB(OH) 2 [37] and CuI [38]. The catalytic effect of metal cations is even more pronounced with methods based on metal salts with non-nucleophilic anions such as LiClO 4 [39], CuSO 4 .5H 2 O [40], Cu(OTf) 2 [41], Al(HSO 4 ) 3 [42], trimethylsilyl triflate [43], which allow the preparation of DHPMs in good to high yields.…”

Section: Introductionmentioning

confidence: 99%

A One-pot Multi-component Synthesis of Dihydropyrimidinone/Thione and Dihydropyridine Derivatives via Biginelli and Hantzsch Condensations using t-BuOK as a Catalyst Under Solvent-free Conditions

Debache¹

2012

TOOCJ

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“…It can be found in the literature several reports of catalytic methods to improve the yields and scope of this reaction. The majority use Brønsted 11 or Lewis acid catalysis, 12 with methods based on metal salts with non-nucleophilic anions having pronounced catalytic activity.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of dihydropyrimidin-2-one/thione library and cytotoxic activity against the human U138-MG and Rat C6 glioma cell lines

Canto¹,

Bernardi²,

Battastini³

et al. 2011

J. Braz. Chem. Soc.

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Duas séries de 4-aril-3,4-diidropirimidin-2(1H)-(tio)onas incluindo monastrol (1a), foram sintetizadas por uma metodologia não agressiva ao meio ambiente baseada no uso combinado de ácido cítrico ou ácido oxálico na presença de TEOF (ortoformato de trietila). A atividade como inibidores da proliferação celular da quimioteca de compostos foi avaliada em duas linhagens de gliomas (U138-MG-humana e C6-rato). Os compostos derivados da tiouréia 1f e 1d mostraram atividade citotóxica maior do que a do monastrol. O composto derivado da uréia 2d apresentou a maior atividade citotóxica dentre todos os compostos analisados.Two series of 4-aryl-3,4-dihydropyrimidin-2(1H)-(thio)ones including monastrol (1a), have been synthesized by an environment-friendly methodology based on the combined use of citric acid or oxalic acid and TEOF (triethylorthoformate). The library was evaluated as inhibitor of cell proliferation on two glioma cell lines (human-U138-MG and Rat-C6). The compounds derived from thiourea 1f and 1d were more cytotoxic than monastrol. The compound derived from urea 2d showed the highest cytotoxic activity among the analyzed compounds.Keywords: dihydropyrimidin-2(1H)-ones, Biginelli reaction, triethylorthoformate, TEOF, monastrol, cancer, glioma IntroductionThe 4-aryl-3,4-dihydropyrimidin-2(1H)-ones (DHPMs) are a class of compounds that has a huge interest in the medicinal chemistry community in recent years.Using high throughput screening (HTS) Mayer et al.1 have evaluated a library of 16,330 small molecules that vary in functional groups and charge. These findings have lead to discover a small molecule which they named monastrol, whose acts by inhibiting the motility of the mitotic kinesin Eg5, a motor protein required for spindle bipolarity. This revealed the potential of this compound as antitumor prototype and since that, some SAR (structure activity relationship) studies concerning this interaction have been performed. 9 This set of potentialities linked to the possibility of chemical modulation in all positions of the dihydropirimidinone/thione rings make DHPMs a privileged structure, justifying the great interest in their synthesis.The original three component reaction of DHPMs consisted of a simple one-pot condensation of benzaldehyde 4b, ethyl acetoacetate 5 and urea 6b (Schemes 1 and 2), catalyzed by few drops of hydrochloric acid under refluxing In this context, we have reported the synthesis of a small library of DHPM, including monastrol (1a), using a Lewis acid as catalyst and this series was evaluated against seven human cancer cell lines. 21 The results showed that the oxo-monastrol analogue (2a) just shows cytostatic activity, while monastrol (1a) was cytotoxic against the seven cancer cell lines. We have also found that the 3,4-methylenodioxy derivative (piperastrol, 1c) was approximately 30 times more potent than monastrol (1a) against five of the seven tested cancer cell lines, and it was also more potent than the positive control doxorrubicine against three of the tested cell lines (Figur...

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Phenylboronic acid as a mild and efficient catalyst for Biginelli reaction

Cited by 107 publications

References 31 publications

Boronic Acid-Catalyzed Reactions of Carboxylic Acids

Boronic Acid-Catalyzed Reactions of Carboxylic Acids

A One-pot Multi-component Synthesis of Dihydropyrimidinone/Thione and Dihydropyridine Derivatives via Biginelli and Hantzsch Condensations using t-BuOK as a Catalyst Under Solvent-free Conditions

Synthesis of dihydropyrimidin-2-one/thione library and cytotoxic activity against the human U138-MG and Rat C6 glioma cell lines

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