Some Michael-Type Reactions with Adenine

Lira, Estephanía; Huffman, C. W.

doi:10.1021/jo01345a028

Cited by 86 publications

(25 citation statements)

References 2 publications

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“…[41] Similarly, adenine reacts with ethyl acrylate and acrylonitrile in the presence of sodium ethoxide forming the corresponding 6-amino-9-b-carbethoxyethylpurine and 6-amino-9-b-cyanoethylpurine in greater than 90% yields (Scheme 16). [42] Adenine also adds to 2-vinylpyridine under neutral conditions forming the corresponding 6-amino-9-b-pyrid-2-ylethylpurine (49% yield). [42] 6-Chloropurine was found to add to acrylonitrile in the presence of catalytic amounts of potassium carbonate yielding up to 73% of 6-chloro-9H-purin-9-ylpropionitrile.…”

Section: Hydroamination Of Functionalized Olefins (Michael Acceptors)mentioning

confidence: 99%

“…[42] Adenine also adds to 2-vinylpyridine under neutral conditions forming the corresponding 6-amino-9-b-pyrid-2-ylethylpurine (49% yield). [42] 6-Chloropurine was found to add to acrylonitrile in the presence of catalytic amounts of potassium carbonate yielding up to 73% of 6-chloro-9H-purin-9-ylpropionitrile. [43] Under similar conditions 2-amino-6-chloropurine reacts with methyl acrylate in the presence of K 2 CO 3 forming the corresponding N-9 and N-7 alkylated products.…”

Section: Hydroamination Of Functionalized Olefins (Michael Acceptors)mentioning

confidence: 99%

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Base-Catalyzed Hydroamination of Olefins: An Environmentally Friendly Route to Amines

Seayad

Tillack

Hartung

et al. 2002

Advanced Synthesis & Catalysis

394

148

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The base‐catalyzed hydroamination of olefins offers a simple and elegant access to various primary, secondary, and tertiary amines. Particular focus is placed on developments in the area of hydroamination of non‐activated olefins. Advantages and disadvantages of the methodology compared to other synthetic methods are presented. Special attention is paid to potential industrial applications of this chemistry.

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Section: Hydroamination Of Functionalized Olefins (Michael Acceptors)mentioning

confidence: 99%

Section: Hydroamination Of Functionalized Olefins (Michael Acceptors)mentioning

confidence: 99%

Base-Catalyzed Hydroamination of Olefins: An Environmentally Friendly Route to Amines

Seayad

Tillack

Hartung

et al. 2002

Advanced Synthesis & Catalysis

394

148

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“…3a crystallized slowly from the solution after cooled to room temperature about 30 min, but 3b-e were formed during the reaction, which could be proved by NMR that the solids filtered completely were expected products. We prepared 6-chloro substituted purine acyclic nucleosides 4, 5, 6 and 9 according to the reported methods, 22 and applied 4-6 to our aminating protocol, then obtained the desired acyclic 6-substituted aminopurine nucleosides 4-6,a-e in high yields after column chromatography purification (entries 15-28 in Table 3). The products 4-6,a-e are new compounds and their structures, proven by NMR, IR and MS, are described in the experimental section and Supplementary Information.…”

Section: Resultsmentioning

confidence: 99%

Microwave assisted synthesis of 6-Substituted aminopurine analogs in water

Qu¹,

Han²,

Zhang³

et al. 2006

J. Braz. Chem. Soc.

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Aminação de derivados de 6-cloropurina em água, assistida por microondas, resultou na preparação de análogos de aminopurina 6-substituídas, em bons rendimentos. Usando um forno de microondas simples, modificado com aparelhagem para refluxo, a aminação do 6-cloro na estrutura da purina ocorreu em condições brandas. Foram preparados 19 análogos conhecidos e 16 desconhecidos de aminopurinas substituídas, através de substituição aromática nucleofílica com filtração simples ou coluna de cromatografia.Microwave assisted amination of 6-chloropurine derivatives with various amines in water resulted in a "green chemistry" protocol for the preparation of 6-substituted aminopurine analogs in very good yields. Using a simply modified microwave oven with the refluxing apparatus, the amination of the 6-chloro in the purine structure occurred smoothly. 19 known and 16 unknown 6-substituted aminopurine analogs were prepared through nucleophilic aromatic substitution with simple filtration or column chromatography.Keywords: amination, 6-substituted aminopurine analogs, nucleophilic substitution, microwave irradiation, amines IntroductionIn modern antiviral and antitumor therapy, an important role is played by modified nucleosides and their analogs, in which modified purine structures are frequently found.1,2 6-Substituted aminopurine analogs, the aminated products of the 6-functional groups in purine structures, continued focusing attention due to their wide range of biological activities (inhibitors of Clostridium feseri growth, 3 cytokinin activity, 4 CIV-CDK (CIV1) and Candida albicans as antifungal medicines, 5 selective kinase, 6 agonists of the A 1 adenosine receptor, 7 the cysteine protease cathepsin K, 8 and platelet aggregation 9 ). Prominent examples of synthetic 6-substituted aminopurine analogs are N-cyclopentyl adenosine (CPA) and N-cyclohexyl adenosine (CHA) (two agonists for the adenosine A 1 receptors). 10The traditional method for the synthesis of 6-substituted aminopurine analogs is the amination of halo, ). However, the complete conversion usually needs 2-24 h and the use of toxic organic solvents or relatively expensive reagents could not be avoided, which dose not conform to the requirement of modern pharmaceutical industry and environmental friendliness.In any case, the development of efficient protocols for the synthesis of aminopurine analogs is still an important goal. Mild reaction conditions, short reaction times and high selectivity and yields are preferable, which makes us pay attention to microwave irradiation. Microwave assisted organic synthesis and functional group conversions have been an increasingly popular field as indicated by numerous publications in the past few years.17 It often leads to rate enhancement, higher yields, easier work-up and better selectivity as well as shortening reaction times compared with the conventional heating methods. In spite of the body of literature about microwave accelerated organic synthesis, the references on the microwave-assisted synthesis of nucleoside com...

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“…Adenine or uracil or thymine was refluxed with ethylacrylate and sodium metal in ethanol for 18 h to produce 3-(adenine-9-yl)propionic acid ethylester, 3-(uracil-1-yl)propionic acid ethylester and 3-(thymine-1-yl)propionic acid ethylester, respectively [27][28][29]36,37]; then the synthesized ester derivatives were converted to hydrazides upon reflux with hydrazine hydrate. The hydrazide was finally coupled to benzoylisothiocyanate to give the thioureido-…”

Section: Synthesis Of Organic Compoundsmentioning

confidence: 99%

“…Literature survey revealed that several purine and pyrimidine derivatives as well as their metal complexes were studied for solvatochromism in different media, this included: purine derivatives [17] and pyrimidines derivatives [18][19][20][21], thiadiazolo and thiazolo pyrimidines [22,23], barbituric and thiobarbituric acid [24,25] and thiophene derivatives [26]. Concerning nucleosides synthesis, adenine and thymine ester derivatives had been prepared via N9 and N1 alkylation, respectively using ethylacrylate [27][28][29], where as the adenine hydrazide preparation was reported by Liu et al [30].…”

Section: Introductionmentioning

confidence: 99%

Solvatochromic absorption and fluorescence studies of adenine, thymine and uracil thio-derived acyclonucleosides

et al. 2015

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Adenine, thymine and uracil thio-derived acyclonucleosides were synthesized and characterized by UV-Vis, FT-IR, 1 H and 13 C NMR spectroscopic techniques. The photophysical properties of the derivatives were evaluated in solvents with diverse polarities and at various pH values. The solvent dependent absorbance and emission spectral shifts were analysed using physical parameters of the selected solvents. The regression and correlation coefficients were calculated using multiple regression techniques. The fitting coefficients gave an estimate of the contribution of each interaction to the total spectral shift in various solutions. Multiple linear regression studies, Kamlet-Taft equation and stokes shift correlation with orientation polarizability provide valuable information concerning spectroscopic characteristics of the studied molecules.

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Some Michael-Type Reactions with Adenine

Cited by 86 publications

References 2 publications

Base-Catalyzed Hydroamination of Olefins: An Environmentally Friendly Route to Amines

Base-Catalyzed Hydroamination of Olefins: An Environmentally Friendly Route to Amines

Microwave assisted synthesis of 6-Substituted aminopurine analogs in water

Solvatochromic absorption and fluorescence studies of adenine, thymine and uracil thio-derived acyclonucleosides

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