One-pot synthesis of 3-(2-cyanophenyl)quinazolin-4(3H)-one

Anthranilonitrile reacting with formic acid at room temperature for three days gave 64% of 3-(2-cyanophenyl)quinazolin-4(3H)-one. Under similar conditions anthranilic acid. 4-nitroaniline, and 2,5-dichloroaniline were N-formylated in good yields.Institute of Organic Chemistry and Technology, Silesian Technical University, Krzywoustego, 4, 44–100 Gliwice, Poland; e-mail: wojtex@zeus.polsl.gliwice.pl. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 922–924, July, 2000.     

An efficient synthesis of new thiazolidin-4-one fused s-triazines as potential antimicrobial and anticancer agents

As a part of our endeavor toward the synthesis of new heterocyclic bioactive agents, two series of thiazolidin-4-one fused s-triazines were synthesized by applying an efficient palladium catalyzed C–C Suzuki coupling using catalyst system Pd(OAC)₂, Xphos and K₃PO₄ as a base in toluene solvent. Moreover, the synthesized analogs were further screened for their in vitro antimicrobial as well as anticancer efficacy against prostate cancer PC3 cells. Some compounds displayed remarkable antimicrobial activity and noticeable anticancer activity. It was observed that, both benzonitrile and nicotinonitrile are essential to increase the different pharmacological activities. The newly synthesized compounds were characterized by IR, 1H NMR, 13C NMR and MS analysis.     

Design,synthesis and immunomodulating activity of C-pseudonucleosides containing thiazolidin-4-one and phenyl connected by acetamide bond

Several novel C-pseudonucleosides containing thiazolidin-4-one and phenyl connected by acetamide bond were rationally designed and easily synthesized at room temperature by using the unprotected sugar aldehyde as the starting material. The effects of the compounds on Con A-induced T cell proliferation were evaluated at five concentrations of 5, 10, 25, 50, and 100 mmol/L Interestingly, compounds 7a and 8a (n = 2, R = H) exhibited immunostimulating activities, while compounds 5a, 6a (n = 1, R = H) and 7b, 8b (n = 2,R = CH₃) showed immunosuppressive activities. Another two compounds 5b and 6b (n = 1,R = CH3) had no immunomodulating activities. These initial biological results suggested that subtle structural changes to the phenyl and acetamide bond of C-pseudonucleosides could have a significant effect on T cell proliferation bias, although it was difficult to formulate a rigorous structureactivity relationship based on the observed activities.     

One-pot synthesis of 2-isopropyl-3-benzyl-1,3-thiazolidin-4-ones and 2-phenyl-3-isobutyl-1,3-thiazolidin-4-ones from valine, arenealdehydes and mercaptoacetic acid

A three-component one-pot synthesis of 2-isopropyl-3-benzyl-1,3-thiazolidin-4-ones and 2-phenyl-3-isobutyl-1,3-thiazolidin-4-ones from valine, arenealdehydes and mercaptoacetic acid with good yields is reported. Characterization of products was generally achieved by NMR techniques and specifically for 2-isopropyl-3-(4-nitrobenzyl)-1,3-thiazolidin-4-one by X-ray crystallography.     

4-氟苯甲醛、β-萘胺和Meldrum酸-锅反应生成1-(4-氟苯基)-1,2-二氢苯并[f]喹啉-3(4H)-酮的反应机理理论研究

采用密度泛函理论(DFT)研究了4-氟苯甲醛、β-萘胺和Meldrum酸一锅反应生成1-(4-氟苯基)-1,2-二氢苯并[f]喹啉-3(4H)-酮的微观反应机理.在B3LYP/6-311G*基组水平上优化了反应物、过渡态、中间体及产物的几何构型,通过振动分析确认了过渡态的结构,并用内禀反应坐标(IRC)确认反应途径.应用分子中的原子理论(AIM)分析了这些物质的成键特征.采用SCRF(PCM)方法研究了反应体系的溶剂化效应.报道了可能的反应路径,其中Re→TS1→IM1→TS2→IM2→TS3→IM3→TS4→IM5→TS7→IM9→TS13→IM10→TS14→P3具有相对较低的活化能,是反应的主要通道,理论预测的主要产物与实验吻合.     

One-pot three-component reaction for the synthesis of pyran annulated heterocyclic compounds using DMAP as a catalyst

The one-pot three-component reaction for the synthesis of pyran annulated heterocycles is reported by condensing aromatic aldehydes, ethyl cyanoacetate, or malononitrile and C-H activated acidic compounds in the presence of catalytic amount of 4-(dimethylamino)pyridine (DMAP) in ethanol under reflux conditions. The significant features of the present protocol are simple, environmentally benign, high yields, non-aqueous work-up procedure, no chromatographic separation and recyclability of the catalyst.     

2-苯基-1-(4-(1-吡咯乙氧基)苯基)乙酮的合成

2-苯基-1-(4-(1-吡咯乙氧基)苯基)乙酮是合成抗骨质疏松药拉索昔芬重要的结构片段。以苯酚为原料经成醚,磺酰氯酯化得到磺酸酯,然后经亲核取代反应,傅-克酰基化反应高收率地合成了目标化合物,其结构通过NMR和HRMS进行了表征。     

A solvent-free synthesis of 1-(4-chlorophenyl)pyrazolidin-3-one in a ball mill

An easy, solvent-free method for the synthesis of 1-(4-chlorophenyl)pyrazolidin-3-one has been achieved by grinding 4-chlorophenyl hydrazine and methyl acrylate in the presence of base in a ball mill. A systematic investigation of the reaction has been made in order to study the various factors affecting the reaction.     

超声技术合成1,5-二-(4-羟基苯基)-1,4-戊二烯-3-酮

利用对羟基苯甲醛和丙酮为原料,以氯化氢气体为催化剂,超声波辐射下成功合成了1,5-二-(4-羟基苯基)-1,4-戊二烯3-酮(HPD).与传统方法相比,该方法具有反应时间短,操作简便及产率高等优点,并讨论了影响产率的因素.     

A new application of diphenylphosphorylazide (DPPA) reagent: convenient transformations of quinolin-4-one, pyridin-4-one and quinazolin-4-one derivatives into the 4-azido and 4-amino counterparts

Herein, we describe a transformation of the oxo-function of a series of quinolin/pyridin/quinazolin-4-ones into 4-azido and thence into 4-amino derivatives in moderate yields by a very short and convenient new procedure using DPPA (diphenylphosphoryl azide) as reagent. A mechanism for this interesting new application of DPPA is suggested based on the identification of some of the intermediates.     

Synthesis of Some Novel 5-(Arylidene)-2-imino-3(pyridin-2-yl)thiazolidin-4-one Derivatives

Treatment of 2-aminopyridine ( 1 ) with chloroacetyl chloride in dry benzene gave 2-chloro-N-(pyridin-2-yl)acetamide ( 3 ), which on further reaction with potassium thiocyanate gave 2-imino-3-(pyridin-2-yl)thiazolidin-4-one ( 4 ) as an intermediate compound for the synthesis of pyridin-2-yl substituted 2-imino-thiazolidine-4-one derivatives. Cyclocondensation reaction of ( 4 ) with a series of aromatic aldehydes gave 5-arylidene derivatives of pyridin-2-yl substituted 2-imino-thiazolidine-4-ones 5a–j . ¹ H and ¹³C NMR spectroscopy, as well as elemental analyses, were used for the identification of these new compounds.     

微波促进下2-氨基-3-氰基-4-芳基-4H- 吡喃化合物的一锅法合成

标题化合物可在微波辐射下以良好的产率经一锅法合成，为2-氨基-4H-吡哺类化合物的制备提供了一种快速便捷的有效方法。     

5-芳酰氨基-2-苯基-2H-1, 2, 4-噻二唑-3-酮的合成

用1-芳酰基-5-苯基-2-硫代双脲与溴进行氧化成环反应制备了九个新的5-芳酰氨基-2-苯基-2H-1, 2, 4-噻二唑-3-酮, 相应的1-芳酰基-5-苯基-2-硫代双脲可以通过苯基脲与酰基异硫氰酸酯加成制得。     

An efficient synthesis of 3-benzylquinazolin-4(1H)-one derivatives under catalyst-free and solvent-free conditions

Abstract

An efficient and convenient method for the preparation of 3-benzylquinazolin-4(1H)-one derivatives under solvent-free and catalyst-free conditions by the reaction of isatoic anhydride, benzylamine, and aromatic aldehydes was reported. In reported papers, ammonia water, ammonium salt, and aromatic amine were often used to synthesize quinazolin-4(1H)-one derivative, but benzylamine was seldom used in this synthesis. This article offers a green method for the synthesis of 3-benzylquinazolin-4(1H)-one derivative used benzylamine as starting material. This methodology has the advantages of short reaction time, mild reaction conditions, easy work-up, and environmental friendliness.     

One-pot multistep synthesis of 3,4-fused isoquinolin-1(2H)-one analogs

We have developed a robust approach for the synthesis of 3,4-fused isoquinolin-1(2H)-one analogs. A benzonitrile or a nicotinonitrile bearing an ortho-substituent, such as -OH, -SH, or -NHR (R = alkyl or aryl) can be deprotonated by KOtBu and then reacted with methyl 2-(bromomethyl)benzoate (8) to form its corresponding O-, S-, or N-alkylation product. The product thus formed is then treated with KOtBu again to initiate a cascade process that will lead to the formation of its corresponding 3,4-fused isoquinolin-1(2H)-one. This multistep synthesis as well as the final product purification is achieved in a one-pot manner.     

用Heck反应合成1-羟基-4-(3-吡啶基)丁-2-酮

在Heck反应条件下,以Ph3P为催化剂配体,由3-卤代吡啶和3-丁烯-1,2-二醇进行偶合可以得到1-羟基-4-(3-吡啶基)丁-2-酮,具有原料易得、合成方法简单的优点.     

A multicomponent synthesis of gem-(β-dicarbonyl)arylmethanes

The reaction of aldehydes with β-dicarbonyls and electron-rich aromatics was investigated to generate in a multicomponent fashion crossed adducts of biological relevance. 4-Hydroxycoumarin, triacetic acid lactone, indole, and a selection of aliphatic and aromatic aldehydes representative of various electronic and steric conditions were employed. The reaction showed a surprising dependence on the solvent, with 1:1 chloroform–water giving the best yield of heterodimeric adducts. The mechanistic rationale for the formation of hetero- rather than homodimeric adducts is discussed.     

An improved procedure for the synthesis of 4-methylimidazol-2-one

A novel one-pot synthetic method of 4-methylimidazol-2-one is described. The target compound is conveniently synthesized from sodium diformylamide, a modified Gabriel reagent prepared, through condensation, hydrolyzation and cyclization reactions without separating intermediates, its total yield is 75.8%.     

4-双(1-苯基-3-甲基-4-吡唑啉-5-酮)甲烷的晶体结构

杂环化合物1 苯基 3 甲基 4 吡唑啉 5 酮(ＨＰＭＰ)为β 二酮,不仅可用作金属离子的萃取剂,还可用于核磁共振的位移试剂,也可用于激光、催化、生化、医学等领域[1-4]。我们从ＰＭＰ出发,合成了它的Ｃｏ(Ⅱ),Ｎｉ(Ⅱ),Ｃｕ(Ⅱ)和Ｚｎ(Ⅱ)的络合物[5,6]。利用单晶Ｘ 射线衍射分析方法报道了标题化合物的晶体结构。1　实验部分在合成ＰＭＰ席夫碱化合物的过程中,得到标题化合物的单晶体。元素分析结果(括号内为计算值)Ｃ%:69 87(69 98),Ｈ%:5 62(5 59),Ｎ:15 61(15 55)。红外光谱(ＫＢｒ):1645和1637ｃｍ-1的强吸收峰归属为羰基的伸缩振动,…     

Effective preparation of 5, 5'-(arylmethylene)bis(4-hydroxythiazole-2(3H)-one) in an aqueous fluoroalcohol solvent system under ultrasound irradiation at room temperature

A green and convenient approach for the synthesis of a series of 5,5'-(arylmethylene)bis(4-hydroxythiazole-2(3H)-one) by the reaction of aryl aldehydes, monochloroacetic acid and ammonium thiocyanate in water/trifluoroethanol(TFE) (1:1) under ultrasound irradiation at room temperature is described. This method provides several advantages such as environmental friendliness, shorter time, excellent yields, and simple work-up procedure.