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The reaction of hydrazine hydrate with certain 2-substituted styryl-4-quinazolones results in the formation of a novel tricyclic heterocycle and not the previously reported acyl hydrazide. A mechanistic rationale is presented.

A variety of quaternary ammonium salts derived from 2-aryl-3-(N, N-dimethylamino)-1-propenes have been converted to the corresponding alkyl and fluoroalkyl ethers by displacement of the ammonium group. This procedure represents an efficient means for the construction of 2-aryl substituted allylic ethers.

Novel β-polyfluoroalkoxy vinamidinium salts 3 and/or 4 were synthesized in good yields by the reaction of N-(2-polyfluoroalkoxy-3,3-difluoro-1-propenyl)trimethylammonium iodides (2), prepared from N-(2,3,3-trifluoro-1-propenyl)trimethylammonium iodide (1), with secondary amines in MeCN at 70 °C for 1 h. The salts were also obtainable in comparable yields by the one-pot reaction of 1 with sodium polyfluoroalkoxide followed by treatment with amines.

The synthesis of two, vinylogous iminium salts, which contain an appended thiophene group, are described along with their conversion to thiophene substituted pyrimidines and pyrroles

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A series of activated polyhalobenzenes have been reacted with various amounts of sodium 2,2,2-trifluoroethoxide in DMF or HMPA. The nature of these monosubstitution and polysubstitution reactions are described.

A series of esters and nitrotoluenes were reacted with Gold's reagent under basic conditions and were found to produce the corresponding dimethylamino methylenenated product in both cases.

A series of activated polyhalobenzenes and polyhaloheteroaromatic compounds have been reacted with a variety of fluoroalkoxide anions. In most cases, regioselective monosubstitution or polysubstitution was observed. The nature of these monosubstitution and polysubstitution reactions is described.

A series of neutral and ionic phase transfer catalysts have been investigated with regard to catalyzing the fluoroalkoxylation of haloaromatic and haloheteroaromatic systems. Poly(ethyleneglycol)8000 and tetrabutylphosphonium bromide were found to be the most effective catalysts. In previous papers1 we have described the fluoroalkoxylation of monohalo and dihaloaromatic and heteroaromatic substrates. Our interest in this reaction stemmed from the need to prepare some fluoroalkoxylated analogs of compound 1 which had been shown2 to be active against a number of harmful insect pests.

The preparation1 of fluorinated compounds continues to be of significant interest to organic chemists due to their diverse and important application as polymers, blood substitutes, pharmaceuticals and pesticides. Considerable attention has been directed to the formation of fluoroalkoxy benzenes with the majority of the synthetic routes involving the reaction of an electrophilic haloalkyl fluoride with a nucleophilic phenol derivative1,2. In a somewhat related procedure, Mendel3 has prepared ortho-2,2,2-trifluoroethoxy methyl benzoate by reacting ortho-hydroxy methyl benzoate with 2,2,2-trifluoroethyl trifluoromethylsulfonate in a potassium carbonate/acetone mixture.

Par reaction avec le bromure de methyl-Mg ou avec des alkyl-lithium, on obtient les aryl-2 alcenes-1 correspondants. Par reduction avec NaBH 4 , obtention des aryl-2 propenes

A variety of organometallic reagents have been found to undergo regioselective reaction with 1-aryl-vinamidinium salts and 3-aryl-3-chloropropeniminium salts. The products of such reactions were found to be α,β-unsaturated ketones and chlorovinyl amines, respectively.

A series of organometallic reagents have been added to a 2-arylsubstituted vinamidinium perchlorate. The resulting reaction mixture was treated with borane or diisobutylaluminum hydride solution to produce a series of 3-substituted-2-aryl-N,N-dimethyl allylic amines. The overall one-pot procedure constitutes a convenient synthesis of 2,3-disubstituted allylic amines.

A series of ortho aminobenzoic acids were treated with Gold's reagent. In each case a 4-hydroxyquinazoline was produced. The resulting transformation constitutes the use of Gold's reagent as a two atom lynch pin.

A variety of quaternary ammonium salts derived from 2-aryl-3-(N, N-dimethylamino)-1-propenes have been converted to the corresponding alkyl and fluoroalkyl ethers by displacement of the ammonium group. This procedure represents an efficient means for the construction of 2-aryl substituted allylic ethers.

A series of ketoximes have been found to react with HMPA in the absence of acid catalysis to produce N,N-dimethyl-N′-arylamidines in reasonable yields.

A variety of 2-aryl-N, N-dimethylallylic amines have been reacted with butyllithium and t-butyllithium to produce the corresponding 3-butyl and 3-t-butyl substituted 2-aryl-propenes. This procedure represents a convenient and clean method for the synthesis of α-substituted styrenes and related substances.

A series of α-β-unsaturated ketones has been reacted with sodium perborate in water and a cosolvent to produce the corresponding epoxides in good yield. The reaction constitutes a mild and convenient method for the synthesis of α-β-epoxyketones.

Two readily available and different quaternary ammonium salts have been prepared by the alkylation of vinamidinium salt reduction products. These salts have been successfully converted to 2-aryl-1-cyano-1-propenes and this methodology represents a clean and efficient procedure for the construction of such systems.

We recently reported1 that [3-(Dimethylamino)-2-azaprop-2-en-1-ylidene] dimethylammonium chloride2 (1) could be reacted with anions derived from ketones or amides to produce enaminones or acylamidines, respectively.

We recently reported1 that “Gold's reagent” (1) is an effective material for the conversion of aryl methyl ketones to the corresponding aryl 8-dimethylaminovinyl ketones.

The reaction of simple iminium salts, such as the Eschenmoser reagent (1) with Grignard and lithium reagents has been recently described1.

A series of activated aryl and heteroaryl dihalides were reacted with HMPA at elevated temperatures. Of the eleven examples studied, all but one reacted in a regioselective manner to give a monohalo-N,N-dimethylamino derivative.

HMPA is known to be an efficient solvent for various anionic reactions. As a consequence of this, we recently1 became interested in using HMPA as a solvent for effecting aromatic nucleophilic substitution between chlorobenzonitriles and sodium 2,2,2-trifluoroethoxide. This application was based on earlier work reported by Shaw2 and Kornblum3 who investigated similar reactions with alkoxide ions.

A variety of quaternary ammonium salts derived from 2-aryl-3-(N,N-dimethylamino)-1-propenes have been reacted with enolate anions derived from several activated methylene compounds. The reactions represent clean and efficient methodology for the elaboration of the 2-aryl-1-propene system.

A series of lactones have been reacted with HMPA at elevated temperatures. In most of the examples studied, unsaturated amides were produced in relatively good yields.

The reaction of hydrazine hydrate with certain 2-substituted styryl-4-quinazolones results in the formation of a novel tricyclic heterocycle and not the previously reported acyl hydrazide. A mechanistic rationale is presented.

A series of α-substituted styrene analogs have been reacted with sodium perborate in acetic acid to produce l-acetoxy-2-aryl-2-propanol analogs in good yield. The reaction constitutes a mild and convenient method for the oxidation of styrene type double bonds.

Effets du solvant, du temps, de la temperature, du groupe depart et du nucleophile sur les reactions d'halogenures d'aryle et d'heteryle avec des trifluoro-2,2,2 ethanolates

A variety of organometallic reagents have been found to undergo regioselective reaction with 1-aryl-vinamidinium salts and 3-aryl-3-chloropropeniminium salts. The products of such reactions were found to be α,β-unsaturated ketones and chlorovinyl amines, respectively.