Synthesis of new pyrimidine derivatives from 2-methyl-3-nitro- and 3-amino-2-methylchromones.

Tanaka, Masaaki; Murakami, Yukitoshi; Morita, H.; Takagi, Kaname

doi:10.1248/cpb.33.2129

Cited by 13 publications

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“…2-Methyl-3-nitrochromone (2) is of importance, because it is used in the preparation of some pharmaceuticals, analgesics, , and nitro and amino N -heterocycles. , The synthesis of 2 has received little investigative attention, , because the starting 2-hydroxy-2‘-nitroacetophenone is not readily available and requires a long procedure for its preparation . Also, direct nitration of 2-methylchromone gives 2-methyl-6-nitrochromone because of the low reactivity of the pyrone ring toward the nitronium ion .…”

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confidence: 99%

Uses of o-Hydroxybenzoylacetone in the Synthesis of Some Substituted 2-Methylchromones, Chelating Agents, and Related Materials

Ibrahim

2000

Ind. Eng. Chem. Res.

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The nitration of o-hydroxybenzoylacetone (1) gave either the unexpected 2,3-benzofurandione 2-oxime or 2-methyl-3-nitrochromone depending on the conditions of the reaction. Nitrosation of 1 gave 1-(o-hydroxybenzoyl)propane-1,2-dione 1-oxime which reacts with hydroxylamine to give 1-(o-hydroxybenzoyl)propane-1,2-dione 1,2-dioxime. Both of the oximes exhibit strong chelating properties. Bromination of 1 gave 3-bromo-2-dibromomethylchromone or 3-bromo-2-methylchromone. The condensation of diethyl malonate with 3-bromo-2-methylchromone was studied as well.

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confidence: 99%

Uses of o-Hydroxybenzoylacetone in the Synthesis of Some Substituted 2-Methylchromones, Chelating Agents, and Related Materials

Ibrahim

2000

Ind. Eng. Chem. Res.

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“…31) Synthesis of Benzopyranyl Amines 3-Aminocoumarin was prepared from salicylaldehyde and acetylglycine according to Chakravarty et al 20,21) 3-Amino-4-methylcoumarin was prepared from hippuric acid via the 2-phenyloxazoline-5-one according to Tripathy and Mukerjee. 22) 3-Aminochromone and 2-methyl-3-aminochromone were prepared by cyclization of 2Ј-hydroxy-2-nitroacetophenone by AcOCHO and Ac 2 O respectively followed by reduction of the 3-nitro moiety according to Becket and Ellis 23) and Tanaka et al 24) The 2Ј-hydroxy-2-nitroacetophenone was obtained by nitration of 4-hydroxycoumarin followed by saponification according to Huebner and Link. 25) 3-Aminoflavone was obtained by nitrosation followed by reduction of the flavanone according to Oyamada and Fukawa 26) and to Shimizu and Nakazawa.…”

Section: Methodsmentioning

confidence: 99%

Synthesis and .ALPHA.-Adrenergic Binding Ligand Affinities of 2-Iminoimidazolidine Derivatives.

Chang-Fong

Benamour²,

Szymonski³

et al. 2000

CHEMICAL & PHARMACEUTICAL BULLETIN

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Venous pathology may result from deficiency of the venous wall contractility. The increase in venous system pressure is due to three main factors: increase of Ca 2ϩ concentration in the smooth muscle cells, decrease of endothelial nitric oxide production and decrease of a-adrenergic receptors (a-AR) of the venous system. 1) Our research efforts to find potentially veinotonic molecules were oriented towards aadrenergic compounds, namely a 2-selective agonists, devoid of any vasoconstrictor side-effect due to a 1-AR activation, a 2-AR being relatively more abundant in veins than in arteries. 1-3) Furthermore, low lipophilicity was needed to avoid hematoencephalic resorption and thus to limit the molecules' central effects. It is also well known that imidazoline compounds enhance spontaneous mechanical activity in rat portal vein 4,5) and antagonize the relaxant effects of the K-channel openers. 4-7) Most a 2-adrenergic agonists belong to the classes of aralkylimidazoline and aryliminoimidazolidine derivatives, best represented by clonidine and moxonidine. With the structure-activity relationships of these aryliminoimidazolidine derivatives in mind, 8-11) we kept intact the 2-iminoimidazolidine fragment of the pharmacophore to preserve a good a 2-AR binding and we only modified the aromatic moiety. Among the various structures of the R moiety linked to the imino group (Chart 1) the choice was made between aliphatic moiety and aromatic moiety which could be ortho substituted. We had a special interest in benzopyranic structures because coumarin and flavonoids are usually used as phlebotomic as well as vascular protecting agents. 12-14) Chemistry The final compounds were obtained by condensation of various amines with imidazoline or imidazolidine (Chart 2) bearing adequate leaving groups in position 2 either pre-existent, as methylthio, or formed in situ as chloro. Starting from 2-imidazolidinethione, the hydriodide salt of 2methylmercaptoimidazoline was prepared by the action of iodomethane 15) and was heated with a moderate excess of a primary amine with or without solvent until the evolution of mercaptan was complete 16,17) (method 1). Starting from Nacetylimidazolidin-2-one, 18) the 2-chloro derivative formed in situ with POCl 3 17,19) was condensed with the primary amine and the acetyl protecting group was finally hydrolyzed (method 2). The initial primary amines were commercially available (series A, B) or prepared according to published procedures (series C). 20-27) The structures of all compounds were confirmed by IR, 1 H-NMR, 13 C-NMR and all final imidazolidine compounds were also confirmed by elemental analyses.

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“…8 In addition, 5-nitropyrimidines have been obtained by ring opening of a 3-nitrochromen-4one. 9 Aside from the viewpoint of an organic chemist, such 5nitropyrimidines are interesting due to their structural similarity to natural compounds, such as bases in nucleosides and nucleotides, and their corresponding physiological activity. Various bioactivities of pyrimidines and other heterocycles are highlighted in a review.…”

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confidence: 99%

Chemistry of Polyhalogenated Nitrobutadienes, 6: A New Ring-Closure Approach to Perfunctionalized 5-Nitropyrimidines

Zapol’skii¹,

Namyslo²,

Altuğ³

et al. 2008

Synthesis

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The recently reported capability of pentachloro-2-nitrobutadiene and some closely related derivatives to allow the synthesis of highly substituted acyclic as well as five-membered (hetero)cyclic compounds is herein extended to pyrimidines with an exceptional substitution pattern. Our novel approach starts from a 1,1-diamino-3,4,4-trichloro-2-nitrobuta-1,3-diene and an appropriate amidine. Some of the resulting perfunctionalized pyrimidines were subjected to further transformations to give promising candidates with respect to biological, especially pharmacological, activity.

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Synthesis of new pyrimidine derivatives from 2-methyl-3-nitro- and 3-amino-2-methylchromones.

Cited by 13 publications

References 0 publications

Uses of o-Hydroxybenzoylacetone in the Synthesis of Some Substituted 2-Methylchromones, Chelating Agents, and Related Materials

Uses of o-Hydroxybenzoylacetone in the Synthesis of Some Substituted 2-Methylchromones, Chelating Agents, and Related Materials

Synthesis and .ALPHA.-Adrenergic Binding Ligand Affinities of 2-Iminoimidazolidine Derivatives.

Chemistry of Polyhalogenated Nitrobutadienes, 6: A New Ring-Closure Approach to Perfunctionalized 5-Nitropyrimidines

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