Synthesis Of N-substituted Pyrroles Research Articles

Microwave-assisted solvent-free tandem cross-metathesis/intramolecular isomerization-cyclization reaction for the synthesis of N-substituted pyrroles: It’s computational analysis

The microwave-assisted solvent-free reaction has been developed for the rapid synthesis of different pyrrole derivatives using cross-metathesis (CM) between N-allylamines and α, β-unsaturated carbonyl compounds with moderate to good yields. This method is solvent free, facile, rapid, and high yielding reaction for the synthesis N-substituted pyrrole derivatives. The effect of microwave irradiation versus classical thermal conditions is demonstrated through a series of comparative cross-metathesis reactions. In the present eco-friendly approach, the combination of solvent-free conditions and microwave irradiations leads to a substantial reduction in reaction times with improved yields. The computational analysis revealed that the microwave irradiation conditions favored the interconversion of ruthenacyclobutane (RuG to RuH) approximately 10-fold more than the conventional heating. Exclusive formation of pyrrole ring system (cyclization- aromatization cascade reaction) over piperazinone (aza-michael product) has been explained through DFT calculations.

Synthesis of Fe3O4@L-proline@SO3H as a novel and reusable acidic magnetic nanocatalyst and its application for the synthesis of N-substituted pyrroles at room temperature under ultrasonic irradiation and without solvent

N-Substituted pyrroles have been prepared in high isolated yields (65–90%) by the reaction of hexane-2,5-dione with amines or diamines in the presence of Fe3O4@L-proline@SO3H at ambient temperature under ultrasonic irradiation and without solvent. The experimental procedure involves simple operations, and the products are readily separated by external magnet. The same reaction of hexane-2,5-dione with amines containing electron-acceptor substituents, such as 4-nitroaniline, resulted in fair yields of pyrrole derivatives.

Acceptorless Dehydrogenative Coupling Using Ammonia: Direct Synthesis of N-Heteroaromatics from Diols Catalyzed by Ruthenium.

The synthesis of N-heteroaromatic compounds via an acceptorless dehydrogenative coupling process involving direct use of ammonia as the nitrogen source was explored. We report the synthesis of pyrazine derivatives from 1,2-diols and the synthesis of N-substituted pyrroles by a multicomponent dehydrogenative coupling of 1,4-diols and primary alcohols with ammonia. The acridine-based Ru-pincer complex 1 is an effective catalyst for these transformations, in which the acridine backbone is converted to an anionic dearomatized PNP-pincer ligand framework.

An efficient synthesis of N-substituted pyrroles catalyzed by MgI2 etherate

AbstractWe describe a convenient and useful procedure for the synthesis of various 2,5-dimethyl-N-substituted pyrrole derivatives by the addition of 2,5-hexadione with aromatic amines, heteroaromatic amines and aliphatic amines catalyzed by MgI

Synthesis ofN-Substituted Pyrroles Catalyzed by Bromodimethylsulfonium Bromide

室温、无溶剂条件下，以溴化二甲基溴化硫（BDMS）为催化剂，以2，5-己二酮和伯胺类化合物为原料，能高收率的实现一系列N-取代吡咯衍生物的合成. 所有化合物结构通过^1H NMR，^13C NMR和元素分析确定.

One-pot tandem reactions for direct conversion of thiols and disulfides to sulfonic esters, and Paal–Knorr synthesis of pyrrole derivatives catalyzed by TCCA

A convenient synthesis of sulfonic esters from thiols and disulfides is described. In situ preparation of sulfonyl chlorides from thiols is accomplished by oxidation with trichloroisocyanuric acid (TCCA), tetra-butylammonium chloride (t-Bu4NCl), and water. The sulfonyl chlorides are then further allowed to react with phenol derivatives in the same reaction vessel. Also, a facile synthesis of N-substituted pyrroles by the reaction of hexane-2,5-dione with primary amines has been accomplished using TCCA as a catalyst under mild condition with excellent yields.

Synthesis of N-Substituted Pyrroles Under Catalyst- and Solvent-Free Conditions

N-Substituted pyrroles were synthesized under neat conditions by the reaction of aromatic amines with 2, 5-dimethoxytetrahydrofuran in excellent yields.

Novel Approach for the Synthesis of N-Substituted Pyrroles Starting Directly from Nitro Compounds in Water

A novel approach for a facile high-yielding synthesis of N-substituted pyrroles has been discovered by the treatment of nitroarenes with 2,5-dimethoxytetrahydrofuran using indium in dilute aqueous HCl at room temperature.

FeCl3-Catalyzed Synthesis of N-Substituted Pyrroles in Water

FeCl₃-Catalyzed Synthesis of N-Substituted Pyrroles in Water

An Approach to the Paal—Knorr Pyrroles Synthesis Catalyzed by Sc(OTf)3 under Solvent‐Free Conditions.

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Homogeneous Polymer-Supported Synthesis of N-Substituted Pyrroles

Homogeneous Polymer-Supported Synthesis of N-Substituted Pyrroles

Efficient N-Alkylation of Pyrrole Under Solid Triphase Transfer Catalysis Conditions. Application to N-Oxyalkyl Pyrroles

Abstract Synthesis of N-substituted pyrroles was easily performed on a large scale under solid triphase transfer catalysis conditions. This method allows to use low reactive alkyl chlorides as the alkylating agents. Small polyethyleneglycol chlorides can also be used as the substituents and yield N-oxyalkyl pyrroles.

Conversion of alcohols into unsymmetrical secondary or tertiary amines by a palladium catalyst. Synthesis of N-substituted pyrroles

The palladium-induced reaction of arylmethanols or allyl alcohols with amines provides a useful method for synthesis of secondary or tertiary amines; N-substituted pyrroles can be prepared by the palladium-catalysed reaction of but-2-ene-1,4-diol with primary amines in excellent yields.