INVESTIGATION OF THE DIRECTION OF THE REACTIONS OF MERCAPTOACETIC ACID ESTERS WITH EPI- AND THIOEPICHLOROHYDRINS

The reactions of mercaptoacetic acid ethers with epi- and thio-epichlorohydrin in alkaline medium have been investigated. It was found that the reaction of mercaptoacetic acid esters with epichlorohydrin in the presence of an equimolar amount of sodium hydroxide simultaneously produces 2,3-epoxy¬pro-pylalkoxycarbonylmethyl sulfides and 1-chlor-3-alkoxycarbonylmethylthiol-2-propanols. Under using sodium hydroxide is used as a catalyst, only 1-chlorine-3-alkoxycarbonylmethyltio-2-propa-nols are obtained the reaction of mercaptoacetic acid esters with epichlorohydrin. As a result of the interaction of mercapto-acetic acid esters with thioepichlorohydrin in the presence of equimolar amounts of sodium hydroxide, 2,3-epitiopropylalkoxycarbonylmethyl sulfides are formed as the only products of the reaction

Synthesis of 2-[(5-Amino-1H-pyrrol-2-yl)sulfanyl]acetic Acid Esters: One-Pot Assembly from Propargyl Amines, Isothiocyanates, and Alkyl­ 2-Bromoacetates

2-[(5-Amino-1H-pyrrol-2-yl)sulfanyl]acetic acid esters have been synthesized in up to 77% yield by the one-pot reaction of lithiated propargylamines with isothiocyanates followed by sequential treatment with t-BuOK–DMSO and alkyl 2-bromoacetates. The process occurs through the initial formation of the thiophene core, followed by its recyclization into the pyrrole nucleus at a higher temperature (ca. 45–60 °C).

An enantioselective synthesis of α-alkylated pyrroles via cooperative isothiourea/palladium catalysis

Herein we describe the direct enantioselective Lewis base/Pd catalysed α-allylation of pyrrole acetic acid esters.