A Michael Addition with 6-Chloropurine<sup>1</sup>

Baker, B. R.; Tanna, Prafullchandra M.

doi:10.1021/jo01019a520

Cited by 27 publications

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“…The mixture was cooled in ice for 51 min. The crystals were collected, using 2 mL water to complete the transfer, sucked with the vacuum for 25 A 0.4000 g sample of Solid A was recrystallized from the solvent pair of 95% ethanol and water. Not all of the sample dissolved in 40 mL of boiling 95% ethanol.…”

Section: -[4-(3-methyl-5-nitro-3h-imidazol-4-yl)piperazin-1-yl]-pyrimentioning

confidence: 99%

“…Subsequently in 1965 Baker and Tanna [25] reported the preparation of 29 by the reaction of 6-chloropurine with acrylonitrile in dimethylformamide as solvent using potassium carbonate, not Triton B, as catalyst. They stirred the reaction mixture at room temperature for 4 h and then let the mixture stand at room temperature for 70 h. In l985 Rosemeyer and Seela [26] prepared 29 using the method of Baker and Tanna.…”

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confidence: 99%

“…They stirred the reaction mixture at room temperature for 4 h and then let the mixture stand at room temperature for 70 h. In l985 Rosemeyer and Seela [26] prepared 29 using the method of Baker and Tanna. Baker and Tanna [25] and Rosemeyer and Seela [26] provided spectral evidence that cyanoethylation of 6-chloropurine occurred at N-9, and not at N-7, of the purine ring.…”

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confidence: 99%

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Preparation of derivatives of 1‐(2‐pyrimidinyl)piperazine as potential antianxiety, antidepressant, and antipsychotic agents

Becker¹

2008

Journal of Heterocyclic Chem

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Section: -[4-(3-methyl-5-nitro-3h-imidazol-4-yl)piperazin-1-yl]-pyrimentioning

confidence: 99%

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Preparation of derivatives of 1‐(2‐pyrimidinyl)piperazine as potential antianxiety, antidepressant, and antipsychotic agents

Becker¹

2008

Journal of Heterocyclic Chem

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“…6-Chloro-9-(2-carbomethoxyethyl)purine, 6-chloro-9-(2-carbo-t-butoxyethyl)purine, and 6-methylthio-9-(2-carbomethoxyethyl)purine were synthesized by the Michael addition of methyl acrylate and t-butyl acrylate to the 6-substituted purine using conditions reported by Baker and Tanna (1965) for the addition of acrylonitrile to 6-chloropurine.…”

Section: Chemicalsmentioning

confidence: 99%

“…Attempts to hydrolyze the t-butyl group from 6-chloro-9-(2-carbo-t-butoxyethyl)purine by aqueous acid catalysis resulted in the simultaneous displacement of the 6-chloro group to yield 9H-hypoxanthin-9-ylpropionic acid (Baker and Tanna 1965). Treatment of an anhydrous ethyl ether solution of the t-butyl ester with anhydrous HCI in ether gave a precipitate that, when isolated, also gave 9-H-hypoxanthin-9-ylpropionic acid upon treatment with ice-H20.…”

Section: Chemicalsmentioning

confidence: 99%

Biological activity of several 9-nonglycosidic-substituted natural cytokinins

Corse

Pacovsky

Lyman

et al. 1989

J Plant Growth Regul

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Abstract.A series of 9-substituted derivatives of four common naturally occurring cytokinins was tested for growth response in the soybean callus assay. The 9-substituents, 2-carboxyethyl (-C2CO2H), 2-carbo-t-butoxyethyl (-C2CO2tBu), and 2-nitriloethyl (-C2CN), all reduced the biological activity of the parent compound. The order of activities was, in general, -C2CO2 H > -C2CO2tBu > -C2CN and followed the unsubstituted cytokinin response pattern ofThe nature of the dose-response curves indicate that the activities of the derivatives are a function of their affinities to a common receptor site and that their steric and polar properties determine that affinity.The 9-(2-carboxyethyl) cytokinins provide a practical alternate source of haptens for the raising of cytokinin antibodies, since sugar-cleavage oxidations are avoided in the preparation of the antigens. E-9-(2-carboxyethyl)-O-13-D-glucopyranosylzeatin (E-ZOG9C2CO2H) was synthesized for the purpose of making antibodies specific for E-O-13-D-glucopyranosylzeatin (E-ZOG) and was also assayed for its growth response.The results obtained with stable 9-substituted cytokinins are useful in defining guidelines for the design of ligands available to explore receptorsite topology.Structure-activity studies for small organic molecules have been very reWarding in a number of fieldsmmedicine, pesticide research, and the study of Reference to a company and/or product named by the Department is only for purposes of information and does not imply approval or recommendation of the product to the exclusion of others Which may also be suitable.

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Synthesis Of Nucleosides

Vorbrüggen¹,

1999

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This chapter deals with the synthesis of nucleosides (e.g., the formation of N ‐glycosides of sugars such as D ‐ribose or 2‐deoxy‐D‐ribose with heterocyclic nitrogen bases). The methods of nucleoside synthesis have been treated in a number of reviews and monographs. It is now generally accepted that nucleosides were among the first organic compounds formed at the start of evolution in the early history of our planet earth. To support this point, guanine and adenine were heated with D ‐ribose in seawater, which contains the Lewis acid magnesium chloride as catalyst. One thus obtained the nucleosides guanosine and adenosine together with comparable yields of unnatural α‐nucleosides. The latter were gradually photoanomerized to the thermodynamically more stable compounds in overall yields of 5–6%. The furanose form of ribose reacts faster than the pyranose form. Corresponding syntheses of the pyrimidine nucleosides uridine and cytidine from uracil , cytosine and ribose are more problematic and remain an enigma. The recent conversion of glycolaldehyde‐ O ‐phosphate and formaldehyde to ribose‐2,4‐di‐ O ‐phosphate might give new insights into the prebiotic syntheses of uridine and cytidine. The evidence and hypotheses for these prebiotic conversions and the evolution of RNA, as well as the implications of an “RNA World,” have been reviewed. These RNA nucleosides are reduced in vivo as 5′‐ O ‐diphosphates by ribonucleotide reductases to the corresponding 2′‐deoxynucleosides—the building blocks of DNA such as 2′‐deoxyguanosine. The thermodynamically controlled synthesis of these four building blocks of RNA has implications for the design of efficient, high yielding, new methods for the synthesis of the naturally occurring nucleosides, nucleoside antibiotics, and modified nucleosides that may serve as antimetabolites to fight viral and parasitic diseases and cancer. The nucleoside rings in this chapter are depicted arbitrarily in the anti conformation, as occurs predominantly in the crystal and solution (based primarily on NOE‐ 1 H‐ and 13 C‐NMR measurements) forms of pyrimidine nucleosides. Only a few nucleosides, such as 6‐methyluridine, occur with the heterocyclic ring predominantly in the syn conformation. The synthesis of C ‐nucleosides has been reviewed previously and is not covered in this review.

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A Michael Addition with 6-Chloropurine¹

Cited by 27 publications

References 0 publications

Preparation of derivatives of 1‐(2‐pyrimidinyl)piperazine as potential antianxiety, antidepressant, and antipsychotic agents

Preparation of derivatives of 1‐(2‐pyrimidinyl)piperazine as potential antianxiety, antidepressant, and antipsychotic agents

Biological activity of several 9-nonglycosidic-substituted natural cytokinins

Synthesis Of Nucleosides

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A Michael Addition with 6-Chloropurine1

Cited by 27 publications

References 0 publications

Preparation of derivatives of 1‐(2‐pyrimidinyl)piperazine as potential antianxiety, antidepressant, and antipsychotic agents

Preparation of derivatives of 1‐(2‐pyrimidinyl)piperazine as potential antianxiety, antidepressant, and antipsychotic agents

Biological activity of several 9-nonglycosidic-substituted natural cytokinins

Synthesis Of Nucleosides

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A Michael Addition with 6-Chloropurine¹