Regioselective dehydrogenation of 3,4-dihydropyrimidin-2(1H)-ones mediated by ceric ammonium nitrate

Tetrahedron

Volumn 62, Issue 41, 2006, Pages 9726-9734

  Shanmugam, P ^a   Perumal, P T ^a  

^a CENTRAL LEATHER RESEARCH INSTITUTE   (India)

Author keywords

3,4 Dihydropyrimidin 2(1H) ones; Ceric ammonium nitrate; Oxidation; Pyrimidines

Indexed keywords

4 PHENYL 1H INDENO[1,2 D]PYRIMIDIN 2,5 DIONE; 5 BENZOYL 2,4 DIOXO 6 (2,4 DICHLOROPHENYL)PYRIMIDIN 2(1H) ONE; 7,7 DIMETHYL 4 PHENYL 7,8 DIHYDROQUINAZOLINE 2,5(1H,6H) DIONE; AMMONIUM NITRATE; BICARBONATE; ETHYL 1,6 DIMETHYL 4 (1 PYRENYL)PYRIMIDIN 2(1H) ONE 5 CARBOXYLATE; ETHYL 1,6 DIMETHYL 4 (4 METHOXYPHENYL)PYRIMIDIN 2(1H) ONE 5 CARBOXYLATE; ETHYL 1,6 DIMETHYL 4 PHENYLPYRIMIDIN 2(1H) ONE 5 CARBOXYLATE; ETHYL 2,4 DIOXO 3 METHYL 6 (3 NITROPHENYL) 1,2,3,4 TETRAHYDROPYRIMIDIN 5 CARBOXYLATE; ETHYL 2,4 DIOXO 3 METHYL 6 (4 CHLOROPHENYL) 1,2,3,4 TETRAHYDROPYRIMIDIN 5 CARBOXYLATE; ETHYL 2,4 DIOXO 6 (1 NAPHTHYL) 1,2,3,4 TETRAHYDROPYRIMIDIN 5 CARBOXYLATE; ETHYL 2,4 DIOXO 6 (2 NITROPHENYL) 1,2,3,4 TETRAHYDROPYRIMIDIN 5 CARBOXYLATE; ETHYL 2,4 DIOXO 6 (3 NITROPHENYL) 1,2,3,4 TETRAHYDROPYRIMIDIN 5 CARBOXYLATE; ETHYL 2,4 DIOXO 6 (4 ANISYL) 1,2,3,4 TETRAHYDROPYRIMIDIN 5 CARBOXYLATE; ETHYL 2,4 DIOXO 6 (4 CHLOROPHENYL) 1,2,3,4 TETRAHYDROPYRIMIDIN 5 CARBOXYLATE; ETHYL 2,4 DIOXO 6 PHENYL 1,2,3,4 TETRAHYDROPYRIMIDIN 5 CARBOXYLATE; ETHYL 3 METHYL 6 [4 [1 METHYL 5 (ETHOXYCARBONYL) 2,6 DIOXO 1,2,3,6 TETRAHYDROPYRIMIDIN 4 YL]PHENYL] 2,4 DIOXO 1,2,3,4 TETRAHYDROPYRIMIDINE 5 CARBOXYLATE; ETHYL 4 (4 METHOXYPHENYL) 6 PHENYLPYRIMIDIN 2(1H) ONE 5 CARBOXYLATE; ETHYL 4 (4 METHOXYPHENYL) 6 TRIFLUOROMETHYLPYRIMIDIN 2(1H) ONE 5 CARBOXYLATE; ETHYL 6 BROMOMETHYL 4 PHENYLPYRIMIDIN 2(1H) ONE 5 CARBOXYLATE; ETHYL 6 METHYL 4 (2 CHLOROPHENYL)PYRIMIDIN 2(1H) ONE 5 CARBOXYLATE; ETHYL 6 METHYL 4 (2 NITROPHENYL)PYRIMIDIN 2(1H) ONE 5 CARBOXYLATE; ETHYL 6 METHYL 4 (2 PROPYL)PYRIMIDIN 2(1H) ONE 5 CARBOXYLATE; ETHYL 6 METHYL 4 (3 HYDROXYPHENYL)PYRIMIDIN 2(1H) ONE 5 CARBOXYLATE; ETHYL 6 METHYL 4 (4 METHOXYPHENYL)PYRIMIDIN 2(1H) ONE 5 CARBOXYLATE; ETHYL 6 METHYL 4 [4 (4 BROMOPHENYL) 1 PHENYL 1H PYRAZOLYL]PYRIMIDIN 2(1H) ONE 5 CARBOXYLATE; ETHYL 6 METHYL 4 BIPHENYLPYRIMIDIN 2(1H) ONE 5 CARBOXYLATE; ETHYL 6 METHYL 4 PHENYLPYRIMIDIN 2(1H) ONE 5 CARBOXYLATE; METHYL 6 METHYL 4 (4 METHOXYPHENYL)PYRIMIDIN 2(1H) ONE 5 CARBOXYLATE; PYRIMIDINONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; DEHYDROGENATION; DRUG STRUCTURE; DRUG SYNTHESIS; OXIDATION; PRIORITY JOURNAL; X RAY CRYSTALLOGRAPHY;

EID: 33748080116     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.07.063     Document Type: Article

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36. 4, formula weight: 308.71, crystal system: monoclinic, space group: P21/n, cell length: a 9.5074, b 15.158, c 9.882, cell angle: α 90°, β 94.149°, γ 90°. Volume (cubic angstroms): 1420.4(5), Z: 4, temperature: 293(2) K, absorption coefficient: 0.28. Calculated density: 1.444, reflections collected/unique 2653/2497 [R(int)=0.0169] R indices (all data) R1=0.0672, wR2=0.0979. Final R indices [I>2σ(I)] R1=0.0377, wR2=0.0861. Crystallographic data was submitted in Cambridge Crystallographic Centre and CCDC no. is 26952.
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