A Facile One-Pot Conversion of Aldehydes into Nitriles

A facile one-pot synthesis of nitriles starting with aldehydes has been developed employing hydroxylamine hydrochloride in dimethylsulfoxide at 100°C.     

SO3H-Functionalized Ionic Liquids: Green, Efficient and Reusable Catalysts for the Facile Dehydration of Aldoximes into Nitriles

Easily synthesized aldoximes have been converted to the corresponding nitriles under very mild conditions by a simple reaction using two halogen‐free SO₃H‐functionalized ionic liquids, 3‐methyl‐1‐(4‐sulfonic acid)butylimi‐ dazolium hydrogen sulfate [MIM(CH₂)₄SO₃H][HSO₄] and 1‐(4‐sulfonic acid)butylpyridinium hydrogen sulfate [PY(CH₂)₄SO₃H][HSO₄], as catalyst and reaction medium without any additional organic solvent. The method was equally effective for aromatic aldoximes bearing electron‐donating and electron‐withdrawing substituents. Taking into account environmental and economical consideration, the protocol presented here has the merits of environmentally friendly, simple operation, easy work‐up and very good yields. The catalysts could be recycled and reused for several times without noticeably decreasing in their catalytic activities.     

A Facile Method for the Synthesis of Acetylcarbazoles and Carbazole Aldehydes

Abstract

Acetylation of 9‐alkylcarbazoles with acetic anhydride catalyzed by PPh₃ · HClO₄ was reported to give acetylcarbazoles. Carbazole aldehydes were easily synthesized by the Vilsmeier reaction of 9‐alkylcarbazoles under microwave condition in good yields.     

PCC-Promoted Dehydration of Aldoximes: A Convenient Access to Aromatic,Heteroaromatic, and Aliphatic Nitriles

A simple and convenient procedure for the synthesis of nitriles by dehydration of aldoximes using a PCC (pyridiniumchlorochromate) has been developed. A variety of aromatic, heteroaromatic, and aliphatic aldoximes are converted.

Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications® for the full spectral details.     

Convenient Method for the Preparation of Carboxylic Esters Using (Chloromethylene)dimethylammonium Chloride

(Chloromethylene)dimethylammonium chloride (Vilsmeier reagent) works as an efficient condensation reagent in the formation of carboxylic esters from carboxylic acids and alcohols under mild conditions in a one-pot procedure. Secondary alcohols are converted successively into the corresponding esters in moderate to high yields with inversion of configurations.     

A Convenient Conversion of Aldoximes to Nitriles Using A Polymer Supported System

Nitriles were readily prepared in excellent yields from the corresponding aldoximes and carbon disulfide under mild and non-aqueous condition in the presence of a regenerable hydroxide form of an anion exchange resin.     

Conversion of Aldoximes into Nitriles with Raney Nickel in Refluxing 2-Propanol

Aldoximes are readily dehydrated to nitriles with Raney nickel in refluxing 2-propanol.     

Convenient preparation of dichloromethyl alkyl ethers

Dichloromethyl alkyl ethers have been synthesized from alkyl formates (C1–C4) and oxalyl chloride in the presence of catalytic amount of N-methylformanilide. N,N-Dimethylformamide is not suitable for the reaction. The method has the advantages of simple experimental procedure, which is applicable to large scale synthesis, without use of harmful reagents.     

A New Method For The Generation of Nitriles From Aldoximes

A mild and efficient method for the stereoselective dehydration of α-aldoximes to the corresponding nitriles is described which utilises methyl (carboxysulfamoyl)triethylammonium hydroxide inner salt (Burgess reagent) as the dehydrating agent.     

New Catalytic Methods for the Preparation of Acetals from Alcohols and Aldehydes

The acetalization of aldehydes has been studied with ethyleneglycol, 3‐chloro‐1,2‐propanediol, 1,2‐propanediol, and 1,2,3‐propanetriol using resin‐D₇₂ catalyst in high yields under reflux and water separator conditions. The reaction is simple, efficient, and chemoselective and does not involve any other additive.     

An Efficient Method for the Preparation of Nitriles via the Dehydration of Aldoximes with Phthalic Anhydride

A new and highly efficient method for the conversion of aldoximes to nitriles was established. By fusing with phthalic anhydride, aldoximes were efficiently and smoothly converted into nitriles, in high yields (over 85%) and in a short time (within 5 minutes). The mixture of phthalic anhydride, a cyclic anhydride, and aldoximes in fusing state set up an ideal transition state for a selective [3.3]‐sigmatropic rearrangement of the acylated aldoximes to nitriles.     

A Convenient Route for the Preparation of Aromatic Aldehydes

Though a variety of methods^2–5 are available for the synthesis of aldehydes, this area continues to attract attention^6,7 since aldehydes are important intermediates in synthetic organic chemistry. In this communication we present a new route for the synthesis of aromatic aldehydes.     

无碱条件下由芳香醛肟和磺酰氯制备O-磺酰基芳香醛肟

在氧化银和碘化钾存在下,磺酰氯与肟室温反应合成一系列O-磺酰基肟.芳香醛肟和酮肟作为底物,产率56%～87%.不过,对硝基苯甲醛肟、脂肪醛肟及α,β-不饱和醛肟作为该反应底物时,没有获得目标产物.     

新型氮芥和卤代烷基哌嗪芳香醛的合成

通过对Vilsmeier反应、烷基化反应和氯化反应的改进提出了以简单易得的苯胺和苯基哌嗪为原料制备氮芥和哌嗪芳香醛的方法. 采用该改进的方法合成了8个氮芥和哌嗪芳香醛, 其中7个为新化合物. 它们的结构均经质谱、红外光谱、核磁共振谱和元素分析确证.     

A Convenient Preparation of Alkyl Nitriles by the Mitsunobu Procedure

A convenient preparation of alkyl nitriles from alcohols extending the use of the Mitsunobu reaction is described. Acetone cyanohydrin is the acidic component and the source of cyanide ion.     

Iron‐Catalyzed Dehydration of Aldoximes to Nitriles Requiring Neither Other Reagents Nor Nitrile Media

The dehydration of aldoximes is an environmentally benign reaction affording the desired nitrile and water as a by‐product. However, most of the reported catalytic dehydration reactions of aldoximes require a solvent containing nitrile to synthesize the corresponding nitrile compounds. Inspired by recent reports on the enzymatic synthesis under nitrile‐free conditions, we here describe that a simple iron salt catalyzes the dehydration of aldoximes requiring neither other reagents nor nitrile media. Our method can be applied to the one‐pot synthesis of nitiriles from aldehydes.     

Polyvinylpyrrolidone-Supported Hydroperoxide for Selective Oxidation of Aldehydes to Carboxylic Acids and Sulfides to Sulfoxides

The facile immobilization of hydroperoxide on the cross-linked poly(vinylpyrrolidone) is described by treatment of a poly(vinylpyrrolidone)-Vilsmeier adduct with (35%) hydrogen peroxide. The in situ–generated poly(vinyl pyrrolidone)-supported hydroperoxide reagent showed very good performance in chemoselective oxidation of aldehydes to carboxylic acids as well as sulfides to sulfoxides.

Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file.     

Efficient and High-Yielding Protocol for the Synthesis of Nitriles from Aldehydes

An operationally simple and high-yielding procedure has been developed for the conversion of araldehydes into the corresponding nitriles using p-toluenesulfonic acid (p-TSA) (a mild catalyst) under microwave irradiation. The products are characterized by infrared spectral analysis and by comparison of the melting and boiling points with the reported values.     

A Convenient Synthesis of Nitrile Oxides from Aldoximes by 1-Chlorobenzotriazole

Nitrite oxides can be conveniently prepared from aldoximes utilizing 1-chlorobenzotriazole in dichloromethane. The reaction and work-up procedures are simple and the isolated yields high.     

Convenient and One-pot Method for Synthesis of the Amino-methylene Bisphosphonic Acid Derivatives from Aldehydes

Bisphosphonic acids and their ester derivatives, carbon analogues of inorganic pyrophos- phate, are the most important organophosphorus compounds and exhibit unique physical and chemical properties in interaction with the alkaline earth cations or heavy m…