The cyclization of o-(alkynyl)-3-(methylbut-2-enyl)benzenes, 1,6-enynes having a condensed aromatic ring at C3-C4 positions, has been studied under the catalysis of cationic gold(I) complexes. The selective 6-endo-dig mode of cyclization observed for the 7-substituted substrates in the presence of water or methanol giving rise to hydroxy(methoxy)-functionalized dihydronaphthalene derivatives is...

The title Schiff base compound, C(13)H(16)N(3)O(+)·PF(6) (-), was derived from the condensation of 2-hydroxy-benaldehyde with the ionic liquid 1-(2-amino-ethyl)-3-methyl-imidazolium hexa-fluoro-phosphate in an ethanol solution. The asymmetric unit comprises one cation and two PF(6) (-) anions. The dihedral angle between the aromatic and imidazole rings is 15.2 (2)°. An intra-molecular O-H⋯N hyd...

In the title Schiff base, C13H9Cl2NO2, which arose from the condensation of 3,4-di-chloro-aniline with 2,3-di-hydroxy-benzaldehyde, the dihedral angle between the aromatic rings is 44.74 (13)°. Intra-molecular O-H⋯O and O-H⋯N hydrogen bonds close S(5) and S(6) rings, respectively. In the crystal, inversion dimers linked by pairs of O-H⋯O hydrogen bonds generate R 2 (2)(10) loops. A weak C-H⋯π i...

The trans-o-hydroxybenzylidene pyruvate aldolase-catalysed reactions between fluoropyruvate and many (hetero)aromatic aldehydes yield aldol adducts without subsequent dehydration. Treatment of the reaction products with hydrogen peroxide yields the corresponding syn-configured α-fluoro β-hydroxy carboxylic acids which have >98 % ee. The overall chemoenzymatic approach, in which fluoropyruvate s...

tryptophan1.2). The formation of 3-hydroxy-4-methylanthranilic acid probably involves a diversion of the well-known metabolic pathway leading to the formation of 3-hydroxyanthranilic acid from L-tryptophan2). However, the mechanismof transmethylation of the aromatic ring has not been examined to the extent of determining which of the alternative compounds mentioned in Fig. 1 is the pentultimate...

Thermic aromatic nucleophilic displacement of the methoxy group at C-6 of (+/-)-1-oxo-2-hydroxy-1,2-dihydroacronycine (2) by an amine is a reaction that gives a facile entry to acronycine derivatives bearing an amino substituent at this position. The introduction of the amino substituents was confirmed with a long-range 1H-15N correlation NMR spectrum at natural abundance. Under basic condition...

We report herein the synthesis of substituted 2-[4-(1,2-dimethyl-5-nitro-1H-imidazol-4-yl)phenyl]-1-arylethanols, ethyl 3-[4-(1,2-dimethyl-5-nitro-1H-imidazol-4-yl)-phenyl]-2-hydroxypropanoate and 2-[4-(1,2-dimethyl-5-nitro-1H-imidazol-4-yl)benzyl]-2-hydroxy-acenaphthylen-1(2H)-one from the reactions of 4-[4-(chloromethyl)phenyl]-1,2-dimethyl-5-nitro-1H-imidazole with various aromatic carbonyl ...

Based on the well known biological versatility of the imidazoline nucleus, we prepared the novel derivatives 3a-k inspired by 2-BFI scaffold to assess imidazoline molecules as D(2)-like dopamine receptor ligands. Conservative chemical modifications of the lead structure, such as the introduction of an hydroxy group in the aromatic ring alone or associated with N-benzyl substitution, provided pa...

The title compound, C(14)H(11)Br(2)NO, was prepared by the condensation of benzyl-amine and 3,5-dibromo-2-hydroxy-benzaldehyde. The crystal structure is stabilized by aromatic π-π stacking inter-actions between the phenol rings of neighbouring mol-ecules [centroid-centroid distance = 3.530 (5) Å]. In addition, the stacked mol-ecules exhibit inter-molecular C-H⋯π and intra-molecular O-H⋯N inter-...

Bacterial metabolism of Tyr and Phe has been associated with the formation of aromatic compounds that impart barny-utensil and floral off-flavors in cheese. In an effort to identify possible mechanisms for the origin of these compounds in Cheddar cheese, we investigated Tyr and Phe catabolism by Lactobacillus casei and Lactobacillus helveticus cheese flavor adjuncts under simulated Cheddar chee...