- Synthesis of Aldehydes by Organocatalytic Formylation Reactions of Boronic Acids with Glyoxylic Acid
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Reported herein is a conceptually novel organocatalytic strategy for the formylation of boronic acids. New reactivity is engineered into the α-amino-acid-forming Petasis reaction occurring between aryl boronic acids, amines, and glyoxylic acids to prepare aldehydes. The operational simplicity of the process and its ability to generate structurally diverse and valued aryl, heteroaryl, and α,β-unsaturated aldehydes containing a wide array of functional groups, demonstrates the practical utility of the new synthetic strategy.
- Huang, He,Yu, Chenguang,Li, Xiangmin,Zhang, Yongqiang,Zhang, Yueteng,Chen, Xiaobei,Mariano, Patrick S.,Xie, Hexin,Wang, Wei
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supporting information
p. 8201 - 8205
(2017/06/30)
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- Synthesis of 5-substituted uracils and 2,4-dimethoxypyrimidines by Wittig olefination
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A variety of new 5-alkenyluracils has been prepared in high yields by Wittig olefination of 5-formyl-l-octyluracil, 5-formyl-1,3-dioctyluracil and 5-formyl-2,4-dimethoxy pyrimidine with stabilized and semistabilized phosphorus ylides. The conformation of the products is discussed on the basis of 1H NMR spectral data.
- Coutouli-Argyropoulou, Evdoxia,Zachariadou, Christina
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p. 1135 - 1142
(2007/10/03)
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- Novel Compounds
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The invention relates to heteroaromatic carboxamides of formula (I), wherein A, R1, R2 and X are as defined in the specification, processes and intermediates used in their preparation, pharmaceutical compositions containing them and their use in therapy.
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- Antiviral pyrimidine nucleosides
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Pyrimidine 4'-thionucleosides of the formula I STR1 wherein Y is hydroxy or amino, and X is chloro, bromo, iodo, trifluoromethyl, C2-6 alkyl, C2-6 alkenyl, C2-6 haloalkenyl or C2-6 alkynyl and physiologically functional derivatives thereof. These compounds have utility as anti-vital agents.
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- Synthesis and cytotoxic activity of 5-(1-hydroxy-2-haloethyl)-, 5-oxiranyl- and (E)-5-(2-iodovinyl)-2,4-dichloro (or dimethoxy) pyrimidines
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A series of 5-(1-hydroxy-2-haloethyl) 6, 7, 13, 14a, 5-oxiranyl 8, 9 and (E)-5-(2-iodovinyl)-2,4-dichloro(or dimethoxy)pyrimidines 11, 12 were synthesized for evaluation as cytotoxic agents. The nuclear C-2 and C-4 substituents were determinants of activity since the 2,4-dichloro compounds 6, 8 and 11 were more potent (ED50 = 0.2-0.3 μg/ml) than the corresponding 2,4-dimethoxypyrimidine analogues 7, 9 and 12 (ED50 = 4-28 μg/ml), relative to melphalan (ED50 = 0.15 μg/ml), in the in vitro L1210 screen. Within the 2,4-dichloro series of compounds 6, 8, 11, the C-5 substitutent was not a determinant of activity. In contrast, in the 2,4-dimethoxypyrimidine series, the C-5 substituents influenced activity significantly where the relative potency order was oxiranyl 9 > -CH(OH)CH2I 7 > (E)-CH = CHI 12 > CH(OH)CHI2 13, CH(OH)CHBr(I) 14a and CH(Br)CHOH(I) 14b. The most active compound (E)-5-(2-iodovinyl)-2,4-dichloropyrimidine 11 exhibited weak activity in the in vivo P388 screen (% T/C = 116 for a 10 mg/kg ip dose) relative to the reference drug 5-fluorouracil (% T/C = 135 for a 20 mg/kg dose).
- Kumar,Knaus,Wiebe,Allen,Tempest
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p. 557 - 562
(2007/10/02)
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- SYNTHESIS OF 5-SUBSTITUTED PYRIMIDINES THROUGH ortho-DIRECTED LITHIATION REACTIONS
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Treatment of 2- and/or 4-substituted pyrimidine with LiTMP in ether at 0 deg C, followed by guenching with various electrophiles afforded the corresponding 5-substituted pyrimidines.
- Wada, Akimori,Yamamoto, Junpei,Kanatomo, Shoichi
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p. 585 - 589
(2007/10/02)
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- Synthesis and biological activity of 5-(2,2-difluorovinyl)-2'-deoxyuridine
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5-(2,2-Difluorovinyl)uracil (IV) was synthesized from 2,4-dimethoxy-5-bromopyrimidine by sequential formylation, difluoromethylenation, and removal of the 2- and 4-methyl groups. Condensation of the trimethylsilyl derivative of IV with protected D-erythro-pentofuranosyl chloride followed by separation of anomers and deblocking gave 5-(2,2-difluorovinyl)-2'-deoxyuridine (V). Compound V was active against herpes simplex virus type 1 (HSV-1) infection as well as tumor cells transformed by the HSV-1 thymidine kinase gene.
- Bobek,Kavai,De Clercq
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p. 1494 - 1497
(2007/10/02)
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