A DMAP-catalyzed mild and efficient synthesis of 1,2-dihydroquinazolines via a one-pot three-component protocol

International audienceAn efficient and simple method for the synthesis of 1,2-dihydroquinazolines catalyzed by 4-(N,N-dimethylamino) pyridine (DMAP) from readily available aromatic or heteroaromatic aldehydes, 2-aminobenzophenone, and ammonium acetate under mild conditions is described. The scope and limitations of the method are discussed

N-[(2-Chloro-8-methyl­quinolin-3-yl)meth­yl]-4-meth­oxy­aniline

In the title compound, C18H17ClN2O, the quinoline ring system is essentially planar; the r.m.s. deviation for the non-H atoms is 0.04 Å with a maximum deviation from the mean plane of 0.026 (4) Å for the C atom bonded to the –CH2– group. The meth­oxy-substituted benzene ring forms a dihedral angle of 70.22 (4)° with this ring system. The crystal structure can be described as zigzag layers in which the quinoline ring systems are parallel to (011) and molecules are connected via inter­molecular N—H⋯N hydrogen bonds, forming chains along [100]. The crystal studied was an inversion twin with a 0.86 (5):0.14 (5) domain ratio

2-Hy­droxy-N-(4-meth­oxy­benz­yl)-4-nitro­anilinium chloride

The crystal structure of the title compound, C14H15N2O4 +·Cl−, can be described as being composed of layers containing both cations and anions that are staggered along [010]. Two types of the hydrogen bonds are observed, viz. cation–anion and cation–cation. The chloride anions are acceptors of the strong hydrogen bonds donated by the secondary amine and the hy­droxy groups. The packing is also stabilized by weak C—H⋯O inter­molecular hydrogen bonds. An intra­molecular N—H⋯O inter­action also occurs

Diethyl 2,6-dimethyl­pyridine-3,5-dicarboxyl­ate at 100 K

In the structure of the title compound, C13H17NO4, the packing is stabilized by weak C—H⋯O and C—H⋯π inter­actions, resulting in the formation of a three-dimensional network

Synthesis of Some New 3-Pyrrolidinylquinoline Derivatives via 1,3-Dipolar Cycloaddition of Stabilized Azomethine Ylides to Quinolinyl α,β- Unsaturated Ketones

International audienceN-Metallated azomethine ylide generated from methyl (E)-N-benzylideneglycinate, LiBr and triethylamine underwent cycloaddition to quinolyl α,β- unsaturated ketones with excellent diastereoselectivity to afford new functionalised 3-pyrrolidinylquinoline derivatives

An Efficient and Recycling Catalyst for the One-Pot Three-Component Synthesis of Substituted 3,4-Dihydropyrimidin-2(1H)-ones

Abstract: The Biginelli one-pot three-component cyclocondensation was applied in this work to prepare 3,4-dihydropyrimidinone and its analogues using the first derivative of lead, Pb(NO 3 ) 2 , as a recycling catalyst, from a diversity of aromatic aldehydes, β-ketoesters and urea. The reaction was carried out in refluxing acetonitrile and afforded the target molecules in good to excellent yields. The method offers several advantages including high yields of the products, short reaction times and easy experimental workup procedure

Ethyl 4-(2-chloro­quinolin-3-yl)-1-phenyl-1H-pyrrole-3-carboxyl­ate

In the mol­ecule of the title compound, C22H17ClN2O2, the dihedral angles formed by the pyrrole ring with the quinoline and phenyl rings are 67.93 (8) and 28.40 (11)°, respectively. In the crystal structure, mol­ecules are linked into dimers by inter­molecular C—H⋯O hydrogen bonds

New eco-friendly procedure for the synthesis of 4-arylmethylene-isoxazol-5(4<i>H</i>)-ones catalyzed by pyridinium <i>p</i>-toluenesulfonate (PPTS) in aqueous medium

<p>In this work we describe a new, highly efficient method for the synthesis of 3-methyl-4-arylmethylidene-isoxazol-5(4H)-one derivatives by a three-component reaction between aromatic aldehydes, ethyl acetoacetate, and hydroxylamine hydrochloride under the influence by PPTS as a low-toxicity, inexpensive, commercially available and easy to handle catalyst. The advantages of this procedure are good yields, short reaction times, simplicity of implementation, and respect of the environment.</p