Catalyst‐Free Efficient Synthesis of Alkyl Acetates Bearing Arylsulfide and Quinoxaline Moieties and Stereoselective Synthesis of Dialkyl 2‐Amino‐3‐thiomalates at Room Temperature

Abstract

A novel and efficient procedure was introduced for the synthesis of alkyl acetates bearing arylthio and quinoxaline moieties from the reaction of o‐phenylenediamines, dialkyl acetylenedicarboxylates, and in‐situ generated arylsulphenyl chlorides in DMF as solvent at room temperature. The procedure worked well for a variety of starting materials and the corresponding products were obtained in good yields. Moreover, some derivatives of dialkyl 2‐amino‐3‐thiomalates were stereoselectively synthesized via the reaction of amines, dialkyl acetylenedicarboxylates and in‐situ generated arylsulphenyl chlorides in moderate to good yields in DCE as solvent at room temperature.

Triethylamine‐Promoted Stereoselective Synthesis of Dialkyl 2‐Thiofumarates by the Reaction of Thiols and Dialkyl Acetylenedicarboxylates

“…During the course of our investigations in this area, [23] we wish to report an efficient stereoselective synthetic route to some new sulfur‐containing fumarates. This procedure offers a facile method for the stereoselective Z ‐type configuration synthesis of a series of desired linearly substituted dialkyl 2‐thiofumarates with good yields.…”

One-pot synthesis of new alkyl 1-naphthoates bearing quinoline, pyranone and cyclohexenone moieties via metal-free sequential addition/oxidation reactions

“…With these considerations in mind, and in the continuation of our efforts to develop new pathways toward the chemical synthesis [30][31][32][33][34][35][36] and as part of our current study on the oxidative cleavages of cyclic vicinal diols to synthesize new potentially biologically active heterocycles, 31 we have herein focused on the development of a facile and effective method for the synthesis of new naphthoate derivatives (Scheme 1). In this study, we report the results of our efforts on the synthesis of various new alkyl 1-naphthoates containing 2,4-dihydroxyquinoline, 4-hydroxy-2pyranone, and 2-hydroxycyclohexenones, starting from acenaphthoquinone and various 1,3-diketones in the presence of different primary alcohols (ROH, R: aliphatic and benzylic groups) as solvent and reagent followed by metal-free H 5 IO 6mediated oxidative cleavage of the corresponding vicinal diols.…”