John T. Gupton

Reactions of β-fluorovinamidinium salt with bifunctional hetero nucleophiles. A new synthetic route to fluorinated heterocycles

Abstract β-Fluorovinamidinium salt (2), readily prepared fromN-(2, 3, 3-trifluoro-1-propenyl)trimethyl-ammonium iodide (1) and diethylamine, reacted with bifunctional hetero nucleophiles such as amidine and guanidine hydrochlorides in the presence of a base to afford regiospecifically monofluorinated pyrimidines4 in good yields. The one-pot procedure starting from1 was applicable for synthesizing heterocyclic compounds4 in almost comparable yields.

Aromatic fluoroalkoxylation via direct displacement of a nitro or fluoro group

Substitution par reaction de nitro- et fluoro-, benzonitrile, -diphenylsulfone, -benzophenone, benzaldehyde, -acetophenone, -benzamide, -benzene-sulfonamide avec des polyfluoroalcanolate de sodium

The application of vinylogous iminium salts and related synthons to the preparation of trisubstituted pyridines

Abstract The reaction of unsymmetrical vinylogous iminum salts and related analogs with β-aminocrotononitrile to yield 2,3,6-trisubstituted pyridines with regioselective control is described.

The Oxidation of α-β-Unsaturated Ketones in Aqueous Sodium Perborate

Abstract 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.

The application of unsymmetrical vinylogous iminium salts and related synthons to the preparation of monosubstituted triazolo [1, 5-a]pyrimidines

Abstract The reaction of vinylogous iminium salts and related analogs with 3-amino-1,2,4-triazole to yield 7-substituted and 5-substituted triazolo [1,5-a]pyrimidines is described.

The preparation and some reactions of a benzotriazole substituted vinamidinium salt

Abstract A three step synthesis of a novel 2-(1-benzotriazolyl)-vinamidinium salt is described along with its direct conversion to a series of unusual 5-(1-benzotriazolyl) pyrimidines, 4-(1-benzotriazolyl)-pyrazoles, and 4-(1-benzotriazolyl) pyrroles.

One Atom Lynch Pin Transformations of Gold's Reagent

Abstract A series of o-phenylenediamines and o-aminophenols have been reacted with Golds reagent to yield benzimidazoles and benzoxazoles, respectively. Additionally, o-hydroxyacetophenone and anthranilamide, when reacted with Golds reagent, were found to produce chromone and 3H-quinazoline-4-one, respectively. These transformations represent the use of Golds reagent as a one atom lynch pin.

A Mild and Convenient Oxidation of Aryl Nitriles to Aryl Amides by Aqueous Sodium Perborate

Abstract A series of benzonitriles has been reacted with sodium perborate in water and a cosolvent to produce the corresponding amides in good yield. The procedure is a mild and convenient alternative for the synthesis of aryl amides.

Regioselective Fluoroalkoxylation and Polyfluoroalkoxylation of Activated Polyhalobenzenes

Abstract 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 Reinvestigation of the Reaction of Hmpa With Ketoximes

Abstract 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.