کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
1346111 980240 2005 6 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
N-Functionalization of uracil derivatives: synthesis of chiral 2-(3-methyl-5-nitro-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)alkanoic acids and their methyl esters
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی معدنی
پیش نمایش صفحه اول مقاله
N-Functionalization of uracil derivatives: synthesis of chiral 2-(3-methyl-5-nitro-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)alkanoic acids and their methyl esters
چکیده انگلیسی

3-Methyl-5-nitro-1-(4-nitrophenyl)uracil has been obtained by regioselective arylation of uracil using 4-nitrofluorobenzene, followed by methylation at the nitrogen atom N-3 and subsequent nitration of the uracil ring. 3-Methyl-5-nitro-1-(4-nitrophenyl)uracil, which was treated with either certain amino acids methyl ester or free amino acids underwent an ANRORC type substitution reaction. Appropriate methyl 2-substituted alkanoates or alkanoic acids containing 3-methyl-5-nitrouracil parts were obtained in satisfactory yields. A similar reaction can be carried out using 5-cyano-3-methyl-1-(4-nitrophenyl)uracil as a substrate.

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Methyl (2S)-(+)-2-(3-methyl-5-nitro-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)propanoateC9H11N3O6Ee >99%[α]D25=+55.8 (c 1.0, CHCl3)Source of chirality: methyl (S)-2-aminopropanoateAbsolute configuration: (2S)

Methyl (2S)-2-(3-methyl-5-nitro-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3-phenylpropanoateC15H15N3O6Ee >99%[α]D25=-22.1 (c 1.0, CHCl3)Source of chirality: (S)-phenylalanine methyl esterAbsolute configuration: (2S)

Methyl (2S)-2-(5-cyano-3-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)propanoateC10H11N3OEe >99%[α]D25=+47.0 (c 1.0, CHCl3)Source of chirality: methyl (S)-2-aminopropanoateAbsolute configuration: (2S)

Methyl (2R)-2-(3-methyl-5-nitro-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)propanoateC9H11N3O6Ee >99%[α]D25=-55.2 (c 1.0, CHCl3)Source of chirality: methyl (R)-2-aminopropanoateAbsolute configuration: (2R)

(2S)-(+)-2-(3-Methyl-5-nitro-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)propanoic acidC8H9N3O6Ee >99%[α]D25=+56.1 (c 1.0, MeOH)Source of chirality: L-alanineAbsolute configuration: (2S)

(2S)-(+)-2-(3-Methyl-5-nitro-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-4-methylpentanoic acidC11H15N3O6Ee >99%[α]D25=+81.1 (c 1.0, MeOH)Source of chirality: L-leucineAbsolute configuration: (2S)

(2S)-(-)-2-(3-Methyl-5-nitro-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3-phenylpropanoic acidC11H13N3O6Ee >99%[α]D25=-90.0 (c 1.0, MeOH)Source of chirality: L-phenylalanineAbsolute configuration: (2S)

(2S)-(-)-2-(3-Methyl-5-nitro-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3-(p-hydroxyphenyl)propanoic acidC14H13N3O7Ee >99%[α]D25=-13.0 (c 1.0, MeOH)Source of chirality: L-thyrosineAbsolute configuration: (2S)

(2R)-(-)-2-(3-Methyl-5-nitro-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)propanoic acidC8H9N3O6Ee >99%[α]D25=-55.8 (c 1.0, MeOH)Source of chirality: D-alanineAbsolute configuration: (2R)

ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Tetrahedron: Asymmetry - Volume 16, Issue 12, 20 June 2005, Pages 2107–2112
نویسندگان
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