Synthesis of five-membered N-heterocycles using silver metal

The heterocyclic chemistry field has been revolutionized using transition metal catalyst in recent years. Various research groups have focused on the development of general protocols to achieve better functional group compatibilities and greater levels of molecular complexity under mild reaction conditions using easily available starting substrates. These methods afford many advantages as compared to alternative pathways involved in the synthesis of heterocyclic compounds. In this review article, we have concentrated on the synthesis of nitrogen-containing five-membered heterocylces in the presence of silver catalyst.     

Synthesis of Some Novel bis‐Spiro[indole‐pyrazolinyl‐thiazolidine]‐2,4′‐diones

The reaction of 1H‐indol‐2,3‐diones with 1,6‐dibromohexane has resulted in the formation of new 1H‐indol‐2,3‐diones‐1,1′‐(1,6‐hexanediyl)bis in quantitative yields. These compounds have been used for the synthesis of novel [3′‐(2,3‐dimethyl‐5‐oxo‐1‐phenyl‐3‐pyrazolin‐4‐yl)spiro[3H‐indol‐3,2′‐thiazolidine]‐2,4′‐dione]‐1,1′‐(1,6‐hexanediyl)bis via bis Schiff's bases, [3‐(2,3‐dimethyl‐5‐oxo‐1‐phenyl‐3‐pyrazolin‐4‐yl) imino‐1H‐indol‐2‐one]‐1,1′‐(1,6‐hexanediyl)bis.     

Facile Denitrosation of Cyclic N-Nitrosamines with Hydrazoic Acid

Abstract

A simple and facile method for the denitrosation of cyclic N-nitrosamines using HN₃ (concentrated H₂SO₄ + NaN₃) is reported. In this method, limited usage of this reagent does not affect the carbonyl group.     

First stereoselective total synthesis of triumfettamide

The first total synthesis of triumfettamide (1) is described. The asymmetric syntheses of two highly functionalized units—α-hydroxylated C17 monounsaturated fatty acid unit (2) and C26 phytosphingosine (3) have been accomplished involving Sharpless asymmetric dihydroxylation, Sharpless kinetic resolution, regioselective epoxide opening, regioselective DIBAL-H reduction of acetal, Wittig olefination as the key steps. Finally N-acylation of phytosphingosine 3 with (2R,6Z)-2-hydroxy-6-heptadecenoic acid 2 followed by DDQ deprotection of PMB, provided target compound 1.     

Ca(Ⅱ)、Mg(Ⅱ)和Zn(Ⅱ)与丙二醇-水混合体系中L-多巴的二元配合物的生成平衡

在303 K恒温条件下,以NaCl为电解质保持离子强度为0.16 mol·L^-1,用pH滴定法研究了M(Ⅱ)-Dopa(多巴)二元配合物在0～60%(V/V)的丙二醇(PG)-水体系中的生成平衡。在PG-水体系中,Ca(Ⅱ)和Mg(Ⅱ)的典型配合物为MLH,ML₂,ML₂H和ML₂H₂,而Zn(Ⅱ)的典型配合物为ML,MLH,ML₂,ML₂H和ML₂H₂。根据静电和非静电力解释了稳定常数随介质的介电常数而变化的倾向。还讨论了在不同组成的丙二醇(PG)-水体系中配合物物种随pH值变化的情况。     

Ca(Ⅱ)、Mg(Ⅱ)和 Zn(Ⅱ)与丙二醇-水混合体系中L-多巴的二元配合物的生成平衡

在303 K恒温条件下,以NaCl为电解质保持离子强度为0.16 mol.L-1,用pH滴定法研究了M(Ⅱ)-Dopa(多巴)二元配合物在0~60%(V/V)的丙二醇(PG)-水体系中的生成平衡。在PG-水体系中,Ca(Ⅱ)和Mg(Ⅱ)的典型配合物为MLH,ML2,ML2H和ML2H2,而Zn髤的典型配合物为ML,MLH,ML2,ML2H和ML2H2。根据静电和非静电力解释了稳定常数随介质的介电常数而变化的倾向。还讨论了在不同组成的丙二醇(PG)-水体系中配合物物种随pH值变化的情况。     

Ugi three-component coupling reaction for the synthesis of 2-(6-oxo-11-phenyl-7,8-dihydrobenzo[b]pyrrolo[1,2-d][1,4]diazocin-5(6H)-yl)-2-phenylacetamide derivatives

A three-component, four center Ugi reaction of 3-(1-(2-aminophenyl)-5-phenyl-1H-pyrrol-2-yl)propanoic acid with aromatic aldehyde and t-butyl isocyanide has been achieved to produce a novel class of N-tert-butyl-2-(6-oxo-11-phenyl-7,8-dihydrobenzo[b]pyrrolo[1,2-d][1,4]diazacine-5(6H)-yl)-2-phenylacetamides in moderate to good yields.     

Ring opening of epoxides with alcohols using Fe(Cp)2BF4 as catalyst

Fe(Cp)₂BF₄ is an efficient catalyst for the alcoholysis of aromatic, aliphatic, and cyclic epoxides giving excellent yields of the corresponding β-alkoxy alcohols under ambient conditions. The methanolysis of styrene oxide using Fe(Cp)₂BF₄ as a catalyst (5 mol %) gave excellent yield of 2-methoxy-2-phenylethanol with complete regio-selectivity. The ring opening of cyclic epoxides gave 77–97% yields of trans-β-methoxy alcohols, in 0.5–6 h. The use of 1,2-epoxyhexane and 1,2-epoxydodecane as substrates gave both regioisomers in excellent yields. The first order rate of reaction with respect to catalyst was observed for the kinetics of ring opening of 1,2-epoxyhexane with methanol.     

Indirect electrochemical oxidation of substituted polycyclic aromatic hydrocarbons to corresponding para-quinones with potassium bromide in water–chloroform medium

Indirect electrochemical synthesis of quinone derivatives of a series of substituted anthracene and naphthalene by the electrolysis of aqueous solution of potassium bromide (3.0 M) using Pt anode at constant current density (40 mA/cm²) has been carried out. These reactions resulted in good to excellent yields of the corresponding para-quinones as confirmed by physical and spectral data.     

Quality by Design Approach for Development of W/O Type Microemulsion-Based Transdermal Systems for Atenolol

The objective of the present investigation was to develop microemulsion-based transdermal systems of highly water soluble drug, Atenolol, by quality by design technique. Atenolol-loaded W/O microemulsions were optimized using D-optimal design with concentrations of oil, surfactants mixture, and water as independent variables, which was converted into microemulsion-based gel (MBG). The results of in vitro permeation of the optimized batch of Atenolol-loaded MBG revealed significant increase in permeability parameters as compared to its convention gel. All results suggested suitability of W/O type MEs as carriers for transdermal delivery of highly water soluble drug, Atenolol.