An efficient and convenient synthesis of pentasubstituted pyrroles from alkyl acetoacetates,dialkyl acetylenedicarboxylates,and amines

A simple and efficient synthesis of pentasubstituted pyrroles has been developed using a one-pot, two-step reaction. The synthesis of a series of 4-hydroxypenta-1,3-diene-tricarboxylates from alkyl acetoacetates and dialkyl acetylenedicarboxylates in the presence of K₂CO₃, followed by cyclization with amines, gave the corresponding pyrroles in excellent yields.     

Synthesis of pyrrolidines,pyrrolines, and pyrroles

As compounds of potential physiological activity, new sulfamide derivatives, Schiffs bases derived from N-arylpyrrolines, are obtained by reacting sulfanilamide, 2-(p-aminobenzenesulfamide) thiazole, 2-(p-aminobenzenesulfamido)-pyrimidine, and 1-phenyl-3-ethyl-4-methyl-5-(p-aminobenzenesulfamido) pyrazole with -(2-chloroethyl)--chlorocrotonaldehyde.For Part XIV see [1].     

Efficient synthesis of pentasubstituted pyrroles via one-pot reactions of arylamines,acetylenedicarboxylates, and 3-phenacylideneoxindoles

An efficient synthetic method for the pentasubstituted pyrroles was successfully developed via the one-pot domino reactions of arylamines, acetylenedicarboxylates, and 3-phenacylideneoxindoles. The reaction mechanism involved the sequential Michael addition and ring closure of the in situ generated β-active enamino ester.     

Atom-economical chemoselective synthesis of 1,4-diynes and polysubstituted furans/pyrroles from propargyl alcohols and terminal alkynes

Under different conditions, the reaction of propargyl alcohols and terminal alkynes leads to the selective formation of 1,4-diynes and polysubstituted furans/pyrroles. Water is the only byproduct in the selective synthesis of 1,4-diynes and pyrroles, and the strategy for the furan synthesis is of 100% atom economy.     

Ruthenium-catalyzed functionalization of pyrroles and indoles with propargyl alcohols

Several ruthenium-catalyzed atom-economic transformations of propargyl alcohols with pyrroles or indoles leading to alkylated, propargylated, or annulated heteroaromatics are reported. The mechanistically distinct reactions are catalyzed by a single ruthenium(0) complex containing a redox-coupled dienone ligand. The mode of activation regarding the propargyl alcohols determines the reaction pathway and depends on the alcohols' substitution pattern. Secondary substrates form alkenyl complexes by a 1,2-hydrogen shift, whereas the transformation of tertiary substrates involves allenylidene intermediates. 1-Vinyl propargyl alcohols are converted by a cascade allylation/cyclization sequence. The environmentally benign processes are of broad scope and allow the selective synthesis of highly functionalized pyrroles and indoles generating water as the only waste product.     

Direct synthesis of pyrroles from imines, alkynes, and acid chlorides: an isocyanide-mediated reaction

[reaction: see text] A direct synthesis of pyrroles from imines, acid chlorides, and alkynes mediated by isocyanides is reported. This reaction proceeds with a range of each of these three substrates, providing a method to generate families of pyrroles in high yield. Mechanistic studies suggest this process proceeds via the generation of imino analogues of munchnones, which can undergo in situ coupling with alkynes to liberate isocyanate and form the pyrrole product.     

An efficient synthesis of pentasubstituted pyrroles: one-pot four-component reaction of arylamine,acetylenedicarboxylate, arylglyoxal,and symmetrical 1,3-dicarbonyl compounds

An efficient and catalyst-free for the synthesis of dialkyl 5-(aryl)-4-(1,3-dicarbonyl)-1-(aryl)-1H-pyrrole-2,3-dicarboxylate via a novel one-pot four-component reaction of arylamine, acetylenedicarboxylate, arylglyoxal, and 1,3-dicarbonyl compounds in ethanol is reported. All the products were obtained in excellent yields and their structures were established from their spectroscopic data.     

Rearrangement of pyrrolines derived from the Birch reduction of electron-deficient pyrroles: radical ring-expansion to substituted tetrahydropyridines

Access to the synthetically important tetrahydropyridine motif has been achieved by radical rearrangement of pyrrolines obtained from the Birch reduction of electron-deficient pyrroles.     

Silver-catalyzed efficient synthesis of enaminones from propargyl alcohols and amines

Enaminones are used as the key intermediates to construct heterocyclic compounds with various bioactivities. In this study, a simple and efficient approach for the synthesis of enaminones via amination of propargyl alcohols was developed. Under the catalysis of Ag₂CO₃, the reaction proceeded smoothly to afford the desired products in good yields. Preliminary mechanism experiments showed that Ag₂CO₃ played an essential role in the procedure of the reaction.     

Transition metal-catalyzed synthesis of pyrroles from dienyl azides

A range of 2,5-disubstituted and 2,4,5-trisubstituted pyrroles can be synthesized from dienyl azides at room temperature using catalytic amounts of ZnI2 or Rh2(O2CC3F7)4.     

New synthesis of pyrroles

The reaction of ammonia or a primary amine with alkyl(cycloaklyl, phenyl)-,-dihalopropyl ketones gives 2-. 2,4-, and 1,2- or 1.2,4-substituted pyrroles in high yields.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 790–793, June, 1976.     

Cationic dirhodium carboxylate-catalyzed synthesis of dihydropyrimidones from propargyl ureas

Cationic Rh(II) complexes are able to catalyze the regioselective hydroamination of propargyl ureas in a 6-endo fashion. This transformation permits access to interesting substitution patterns of dihydropyrimidines, which have found use as nucleotide exchange factor inhibitors.     

Palladium-catalyzed synthesis of pyrroles

Pyrrole derivatives are prepared in high yields by the catalytic action of a Pd(II) salt on 1-amino-3-alkyn-2-ols which are obtained from conjugate ynones.     

A new and general one-pot synthesis of propargyl alcohols from esters

Intermediates easily prepared by partial reduction of various esters with LDBBA as a reducing agent smoothly react with lithium acetylides to give propargyl alcohols, without isolation of partial reduction intermediates, in good yields (73-83%).     

The silylalkyne-Prins cyclization: stereoselective synthesis of tetra- and pentasubstituted halodihydropyrans

[reaction: see text] A new type of Prins cyclization using silylated secondary homopropargylic alcohols and aldehydes yielding tetra- and pentasubstituted dihydropyrans is described. The presence of the trimethylsilyl group in the triple bond favors the Prins cyclization and minimizes the 2-oxonia-[3,3]-sigmatropic rearrangement as a competitive alternative pathway. Ab initio theoretical calculations of the species involved in the rearrangements support the proposed mechanism. The process is highly stereoselective, affording cis-dihydropyran as the only isomer.     

Direct synthesis of pyrroles via a silver-promoted three-component reaction involving unusual imidazole ring opening

A novel silver-promoted three-component reaction toward the synthesis of multifunctionalized pyrroles has been developed. This reaction involves an unusual imidazole ring decomposition, presumably via 1,5-isomerization and subsequent hydrolysis.     

A new synthesis of pyrroles

The radical reaction between an N-ethylsulfonylenamide and an alpha-xanthyl ketone gives an intermediate gamma-keto imine which spontaneously ring-closes to the pyrrole.     

An efficient one-pot synthesis of pyrrolines and tetrahydropyridines from their chloro-precursors via in situ aza-Wittig reaction

A simple and efficient method for synthesizing pyrrolines and tetrahydropyridines via an intramolecular aza-Wittig reaction has been achieved by microwave irradiation of the corresponding chloro-alkane derivatives in the presence of tertiary phosphite and sodium azide. The in situ formation of the alkyl azides makes this a facile and safe method for aza-Wittig reactions.     

Simple synthesis of substituted pyrroles

Simple synthesis of substituted pyrroles using iodine-catalyzed and montmorillonite KSF-clay-induced modified Paal-Knorr methods has been accomplished with excellent yields. N-Substituted carbazole has also been prepared by following this method. If one of the reactants is a liquid, the reaction proceeds exceedingly well without a solvent. This method gives pyrroles with less nucleophilic multicyclic aromatic amines at room temperature.