A convenient two-step synthesis of 6-methylenesubstituted-4-trichloromethyl-2-methylsulfanyl pyrimidines

Zanatta, Nilo; Flores, Darlene C.; Madruga, Claudia C.; Flores, Alex F. C.; Bonacorso, Hélio G.; Martins, Marcos A. P.

doi:10.1016/j.tetlet.2005.11.035

Cited by 22 publications

(26 citation statements)

References 16 publications

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“…Such reactions were proven to be effective in parent compounds previously synthesized by our research group. [34][35][36] At this point, it is important to mention that we could not find any reports regarding the elimination of the -CF 3 group in cyclocondensation reactions. Searching for an explanation for this observation, we found an X-ray study that showed interactions between the fluorine of fluorinated molecules and the sp-carbon of the acetonitrile (C-F•••C≡N).…”

Section: Entrymentioning

confidence: 83%

Trifluoromethyl β‐Enamino Diketones as Dual Substrates for the Synthesis of 5‐Benzoyl‐6‐(trifluoromethyl)pyrimidines and their Pyrimidin‐4(3H)‐one Analogues

et al. 2020

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A regio‐ and chemoselective method for the preparation of 6‐trifluoromethyl‐5‐benzoyl‐2‐methylsulfanyl pyrimidines and their pyrimidin‐4(3H)‐one analogues, from the cyclocondensation reaction of trifluoromethyl β‐enamino diketones with non‐symmetric 2‐methylisothiourea sulfates is reported. These diketones functioned as dual substrates by providing both products with high regioselectivity (only N3‐substituted isomer was observed) and high chemoselectivity. A new feature provided by the starting material proposed herein is the possibility to either maintain or eliminate the trifluoromethyl group, by choosing the solvent.

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Section: Entrymentioning

confidence: 83%

Trifluoromethyl β‐Enamino Diketones as Dual Substrates for the Synthesis of 5‐Benzoyl‐6‐(trifluoromethyl)pyrimidines and their Pyrimidin‐4(3H)‐one Analogues

et al. 2020

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“…The structures of compounds 2-7 and 9 were determined by 1 H, 13 C NMR, gas chromatography-mass spectrometry (GC-MS), elemental analyses, high resolution mass spectrometry (HRMS) and by comparison with NMR data of other compounds previously synthesized in our laboratory. 39,40 The 4,5-dihydropyrazoles 2a-c and 4,5-dihydroisoxazole 4 show the chemical shifts of the methylene protons of the ring (H-4a and H-4b) to be a characteristic of the AB system and as a doublet on average near δ 3.1 and 3.4 ppm, respectively, with a geminal coupling constant in the range of [18][19] In comparison with the compounds 2a-c, the pyrazoles 3a-f showed 1 H NMR chemical shifts in CDCl 3 for the proton H-4 as a characteristic singlet at an average of δ 6.7 ppm. The C-5 of the compounds 2-4, 7 and 9 shows signals in the shape of quartets, with 2 J C-F in the range of 33-41 Hz.…”

Section: Resultsmentioning

confidence: 99%

“…Since the trifluoromethyl group shows changes in physico-chemical properties such as polarity, lipophilicity and polarizability, chemical behavior, 1 and pharmacological activity of the molecules to which it is connected, 2,3 this substituent has become increasingly popular in heterocyclic compounds synthesized for biological application. [4][5][6] Over the last twenty years our research group (NUQUIMHE) has reported on the synthetic potential of β-alkoxyvinyl trihalomethyl ketones for obtaining of new trihalomethylated heterocycles, [7][8][9][10][11][12] as well as other molecules that provide great possibilities for chemical heterocycles containing a stable dimethyl acetal-protected aldehyde function as a substituent for further chemical transformations has not yet been described. So, the one-step synthesis of heterocycles that have a protected aldehyde function (such as an acetal moiety) deserves considerable attention.…”

Section: Introductionmentioning

confidence: 99%

Easy and regioselective access to dimethyl acetal-protected heterocycles and their efficient allylation reactions mediated by allylaluminum reagent

Bonacorso¹,

Wiethan²,

Porte³

et al. 2013

Arkivoc

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This paper describes easy access to twelve examples of five-and six-membered heterocycles (monocyclic and fused) containing a dimethyl acetal aldehyde function and/or a trifluoromethyl substituent, in good to excellent yields (72-98%). The dimethyl acetal-protected heterocycles were obtained in one-step via regioselective cyclocondensation reactions of 4,6,6-trimethoxy-1,1,1-trifluorohex-3-en-2-one with 1,2-, 1,3-and 1,5-dinucleophiles (hydrazines, hydrazides, hydroxylamine, 1-acetylguanidine and 1,8-diaminonaphthalene). Subsequently, to demonstrate a potential synthetic application, some pyrazole rings containing dimethyl acetal moiety were converted to the respective secondary homoallylic alcohols by efficient allylation reactions employing allylaluminum reagent in 84 to 90% yields.

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“…[137][138][139][140][141][142][143][144][145][146][147][148][149] Foram utilizados por esse grupo, principalmente, os derivados de 4-alcoxi-1,1,1-tricloro-alquen-2-onas, que, conforme já mencionado, são reagentes de larga versatilidade. Mais recentemente, o mesmo grupo desenvolveu novas metodologias sintéticas utilizando energia de micro-ondas e ultrassom.…”

Section: Heterociclos Contendo -Cxunclassified

Recentes aplicações sintéticas de compostos orgânicos tricloro(bromo)metila substituídos

Menezes¹,

Gallardo²,

Zucco³

2010

Quím. Nova

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Recebido em 1/7/10; aceito em 11/10/10; publicado na web em 16/11/10 RECENT SYNTHETIC APPLICATIONS OF TRICHLORO(BROMO)METHYL CONTAINING ORGANIC COMPOUNDS. This review presents the recent applications of some trihalomethyl carbinols, α,α,α-trihalogenated carbonyl compounds and trichloro(bromo)methyl-containing heterocycles, acting as high versatile synthetic precursors in organic chemistry, based on the last 10 years' literature.Keywords: trichloro(bromo)methyl compounds; synthetic applications. INTRODUÇÃO O grupo tricloro(bromo)metilaCompostos orgânicos contendo grupos -CCl 3 ou -CBr 3 em suas estruturas possuem diversas aplicações em diferentes áreas como bioquímica, agroquímica, produtos naturais, mas são reconhecidos, sobretudo, como reagentes altamente versáteis em síntese orgânica. O clorofórmio, por exemplo, o derivado mais simples contendo o grupo -CCl 3 , é um solvente de larga utilização em laboratórios. A Figura 1 mostra alguns compostos contendo o grupo -CX 3 , dotados de interessantes propriedades. O DDT, 1, é o inseticida mais conhecido da história.1 O composto piridínico 2 é relatado como um agente antitumoral 2 e o derivado arsênico 3 possui atividade antileucêmica.3 O grupo -CCl 3 é fundamental para a atividade biológica do Salubrinal, 4, uma molécula altamente eficaz na proteção de células sadias contra apoptose induzida por estresse excessivo e incorreto do retículo endoplasmático, fato responsável por importantes patologias como diabetes, Alzheimer e infecções virais. 4,5 Com relação aos derivados contendo o grupo -CBr 3 , destaca-se o agente neurotóxico 5.6 Já o composto 6 é um dos componentes da alga vermelha Asparagopsis Taxiformis, que apresenta atividade contra aldose redutase em bovinos. 7 Aplicações sintéticas de compostos orgânicos contendo -CX 3O desenvolvimento de novas estratégias e metodologias em sín-tese orgânica é um acontecimento recorrente e promissor de pesquisa em Química, e, nesse contexto, compostos orgânicos contendo o grupo -CX 3 (X = Cl, Br) têm sido citados na literatura como reagentes úteis e versáteis em diversas circuntâncias. Nesta revisão, serão apresentados exemplos relatados, principalmente na última década, envolvendo a utilização de tri-halometil carbinois (THMCs), compostos carbonilados α,α,α-tri-halogenados (CCTHs) e heterociclos contendo -CX 3 como precursores sintéticos de funções químicas variadas. Esses compostos atuam, muitas vezes, como peças fundamentais em estratégias de síntese de moléculas altamente elaboradas e de acentuada importância.Em 1934, Fuson e Bull publicaram um artigo de revisão acerca da reação do halofórmio, apontando, já naquela época, utilização dessa reação em análises qualitativas e quantitativas, suas aplicações em síntese e explicações mecanísticas. 8 De fato, a reação do halofórmio é uma das mais antigas na Química. Em 1822, Serulla, acidentalmente, verificou que o tratamento de etanol com hipoiodito, formado a partir de iodo em solução básica de hidróxido, levava à obtenção de iodofórmio e íon formato, por reação de oxidação do...

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A convenient two-step synthesis of 6-methylenesubstituted-4-trichloromethyl-2-methylsulfanyl pyrimidines

Cited by 22 publications

References 16 publications

Trifluoromethyl β‐Enamino Diketones as Dual Substrates for the Synthesis of 5‐Benzoyl‐6‐(trifluoromethyl)pyrimidines and their Pyrimidin‐4(3H)‐one Analogues

Trifluoromethyl β‐Enamino Diketones as Dual Substrates for the Synthesis of 5‐Benzoyl‐6‐(trifluoromethyl)pyrimidines and their Pyrimidin‐4(3H)‐one Analogues

Easy and regioselective access to dimethyl acetal-protected heterocycles and their efficient allylation reactions mediated by allylaluminum reagent

Recentes aplicações sintéticas de compostos orgânicos tricloro(bromo)metila substituídos

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