Facile Synthesis of 1,2-Dialkyl-3-Phenyl-4-Quinolinones

The synthesis of 1,2-dialkyl-3-phenyl-4-quinolinones (1) is readily accomplished by a low-temperature reaction of an N-alkylisatoic anhydride with the therraodynamic potassium enolate of phenyl-acetone. The reaction has also been extended to encompass the synthesis of the more complex 2-(3-hydroxy-propyl)-3-(4-fluorophenyl)-1-methyl-4(1H)-quinolinone (10).     

Conformational Behaviour of Substituted 2-Methoxy-2-Oxo-1,2-Oxaphospholan-3-Ols

Abstract

Conformational behaviour of about 30 2-methoxy-2-oxo-1,2- oxaphospho l an-3-0 1 s containing various substituents was examined by ¹H and ¹³C NMR. Vicinal coupling constants J(HCCH), J(HCCP), J(HCOP), J(CCOP) and J(CCCP) were employed in this study. Conformation of the 1,2-oxaphospholane ring is governed almost exclusively by substituents at C-3, C-4 and C-5, as we l l as by their orientation. The configuration of the P atom has little or no influence on conformation of the ring in diastsreomeric pairs. Strong preference of phenyl, methyl and substituted methyl groups to occupy the equatorial or pseudoequatoria l positions was observed for all but one compounds studied. In the cis-fused bicyclic syst ems conformat ionally rigid 6-membered rings forced the 1,2-oxaphospholane rings to adopt an enve l ope-l ike (E₄) conformation. No influence of the p=o……HO-C-3 hydrogen bond on conformation of the 1,2-oxaphospholane ring was found. Preferred conformations for (2R, 3R, 4R)-3-(hydroxymethyI)-2-methoxy-2-oxo-1,2-oxaphospho lane-3,4-diol and its triacetate are shown below.     

Ferric Chloride-catalyzed Synthesis of 2-Oxo-1,2-dihydro-1,8-naphthyridine-3-carboxylate Derivatives and Their Biological Evaluation

Russian Journal of General Chemistry - A new methodology has been developed for the synthesis of novel 2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxylates from 2-aminonicotinaldehyde,...     

Alkylation of 3-Ethoxy-2-Lithioacrylonitrile: Synthesis of 5-Alkylcytosines

The utility of commercially available, inexpensive 3-ethoxyacrylonitrile (1) as a precursor for the synthesis of 5-alkylcytosines was investigated. Metalation of 1 affords a 2-lithio derivative of sufficient stability to allow alkylation with allylic or benzylic bromides and primary iodides which are unbranched at the β-position. The alkylated derivatives are converted to 5-alkylcytosines in modest yield by exposure to sodium ethoxide and urea in ethanol.     

1-苯基-5-芳基-1,2-二氢-1,2,4-三唑-3-硫酮的合成

将取代苯甲酰氯1a～1f与硫氰酸钾反应, 得到的中间体不需纯化直接与苯肼反应, 成功地合成了1-苯基-5-芳 基-1,2-二氢-1,2,4-三唑-3-硫酮(2a～2f). 化合物2的结构通过红外光谱、核磁共振光谱和高分辨质谱进行了表征.     

sym-Triazine Derivatives. 2. Synthesis, Properties, and Structure of 2-Oxo-1,2-dihydro-sym-triazines

Previously unreported 2-oxo-1,2-dihydro-sym-triazines have been prepared and their alkylation reactions have been studied. It was found that, independently of the structure and nature of the substituent in positions 4 and 6 of the triazine ring or the structure of the alkyl halide used, the reaction occurs regioselectively at the oxygen atom. The stereostructure of the 2-oxo-1,2-dihydro-sym-triazines was investigated by X-ray analysis and it was shown that they exist as dimers in the crystalline state.     

Synthesis of 3,5-Diaryl and 3,5-Dialkyl-1,2-dithiolylium-4-olates

Abstract

Sulfurization of 2-acetoxy or 2-benzoyloxy-1,3-propanediones gives the corresponding 1,2-dithiolylium salts which are used as starting materials for preparation of 1,2-dithiolylium-4-olates.

The reaction was studied under different conditions in order to obtain the best sulfurization yields.

A new 3-p-dimethylaminophenyl-5-phenyl-1,2-dithiolylium-4-olate is also described. It is formed by nucleophilic attack on a 3-alkylthio substituted or a 5 unsubstituted position of a 1,2-dithiolylium ion by N, N-dimethylaniline.     

Ene Synthesis of Bicyclic Arylmethylenedihydropyrazoles Using 4-Phenyl-4,5-dihydro-3H-1,2,4-triazole-3,5-dione

8-Acetyl-7-aryl-2-arylmethylene-8,9-diaza- and 4,8,9-triazabicyclo[4.3.0]non-9-enes react with4-phenyl-4,5-dihydro-3H-1,2,4-triazole-3,5-dione, following the ene addition pattern. Under similar conditons 7-aryl-2-arylmethylene-8-methyl-8,9-diazabicyclo[4.3.0]non-9-enes give rise to both mono- and polyadditionproducts. The product structures were studied by ¹H and ¹³C NMR, IR, and UV spectroscopy and singlecrystal X-ray diffraction.     

3-Phenyl-2-benzofuranon

Ohne Zusammenfassung     

Synthesis of Substituted 2-Oxo-2,3-dihydro-1H-imidazo-[1,2-a]indole-6,7-dicarbonitriles

A three-step procedure has been developed for the synthesis of 2-oxo-2,3-dihydro-1H-imidazo-[1,2-a]indole-6,7-dicarbonitriles from substituted 2-amino-1-hydroxy-1H-indole-5,6-dicarbonitriles.

     

2-Aryl-3,5-dinitro-1,2-dihydropyridines

The reaction of -nitroacetaldehyde with paraformaldehyde or aromatic aldehydes and ammonium acetate in acetic acid yielded 2-aryl-3,5-dinitro-1,2-dihydropyridines. Aromatic aldehydes, in an ethanol and acetic acid mixture, gave isomeric 3,5-dinitro-1,4-dihydropyridines in addition to 1,2-dihydropyridines. Physicochemical properties and reactivities of the compounds have been studied.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 64–70, January, 1993.     

One-Pot Green Synthesis of 2-Oxo-2H-chromene-3-carbonitriles Using Dual-Frequency Ultrasonication

Russian Journal of Organic Chemistry - A green synthesis of 2-oxo-2H-chromene-3-carbonitriles has been carried out in one step by reacting 2-hydroxybenzaldehydes or 2-hydroxyacetophenones with...     

Synthesis of 3-Oxo-2,3-Dihydroisoquinolines from Ethyl 2-Acylphenylacetates and Formamides

1- and 1,3-substituted 3-oxo-2,3-dihydroisoquinolines 4 are obtained from ethyl 2-acylphenylacetates 3 and formamides.     

2-苯基-6-肼基-3-哒嗪酮类化合物的合成与表征

报道了醚氧乙酰肼类化合物在氢氧化钠存在下可以重排为有机肼类化合物的新方法.该方法适宜于合成多种取代的2-苯基-6-肼基-3-哒嗪酮类化合物.产物通过IR,1HNMR,13CNMR等方法进行了表征.