- Pyridine-derived heterocycles as potential photoacylating reagents
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We prepared several pyridine-derived heterocycles and investigated their photoacylating properties. Among representatives of 4 families of compounds (1-acetyl-7-azaindole, 1-acetyl-7-azaindoline, 2-acetamindpyridine and 2-amidopyrimidines), the 2-aminopyrimidine derivatives were the most promising candidates. Photoacylation of dodecylamine yields up to 47% were obtained, upon irradiation with UV light at 254 nm.
- Helgen, Celine,Bochet, Christian G.
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- A designed amide as an aldol donor in the direct catalytic asymmetric aldol reaction
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The direct catalytic asymmetric aldol reaction offers efficient access to β-hydroxy carbonyl entities. Described is a robust direct catalytic asymmetric aldol reaction of α-sulfanyl 7-azaindolinylamide, thus affording both aromatic and aliphatic β-hydroxy amides with high ee values. The design of this transformation features a cooperative interplay of a soft and a hard Lewis acid, which together facilitate the challenging chemoselective enolization by a hard Bronsted base.
- Weidner, Karin,Kumagai, Naoya,Shibasaki, Masakatsu
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supporting information
p. 6150 - 6154
(2014/06/23)
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- RING-TRANSFORMATIONS OF PYRIMIDINES BY INTRAMOLECULAR DIELS-ALDER REACTIONS. SYNTHESIS OF ANNELATED PYRIDINES
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Pyrimidines carrying an ω-alkyne side-chain -XCH2CH2CCH (X=O,N,S,SO,SO2) at the 2 or 5 position undergo intramolecular inverse electron demand Diels-Alder reactions across the C-2 and C-5 positions; elimination of hydrogen (or alkyl) cyanide from the intermediate adducts leads to condensed pyridines.The influence of the hetero atom (X) in the dienophilic side-chain and that of substituents in the pyrimidine ring on the reactivity is discussed.
- Frissen, A. E.,Marcelis, A. T. M.,Plas, H. C. van der
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p. 803 - 812
(2007/10/02)
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- NOVEL RING TRANSFORMATIONS OF PYRAZINES BY INTRAMOLECULAR DIELS-ALDER REACTIONS
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Pyrazines carrying the ω-alkyne side-chain -XCH2CH2CH, (X = O,N,S,SO,SO2,C(CN)2) undergo on heating an intramolecular Diels-Alder reaction.Pyrazines with the electron donating atom (O,N or S) in the side-chain afford -fused pyridines as main products, whereas (3-butynylsulfinyl)pyrazine and (3-butynylsulfonyl)pyrazine are exclusively converted into -fused pyridines.A -fused pyridine is also the major product in the reaction of 2,5-bis(1,1-dicyano-4-pentynyl)pyrazine.
- De Bie, D.A.,Ostrowicz, A.,Geurtsen, G.,Van Der Plas, H.C.
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p. 2977 - 2984
(2007/10/02)
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