Acetylenic esters. II. Further addition reactions with sulfur- and nitrogen-containing compounds

Some nitrogen and sulfur containing compounds as chemotherapeutic agents.

Addition-substitution reactions of 2-thio-3-chloroacrylamides with carbon, nitrogen, oxygen, sulfur and selenium nucleophiles.

Synthetically versatile conjugate addition of a range of carbon, nitrogen, oxygen, sulfur and selenium nucleophiles to the highly functionalised 2-thio-3-chloroacrylamides is described. The stereochemical and synthetic features of this transformation are discussed in detail. In most instances, the nucleophile replaces the chloro substituent with retention of stereochemistry. With the oxygen nuc...

Influence of Sulfur for Oxygen Substitution in the Solvolytic Reactions of Chloroformate Esters and Related Compounds

The replacement of oxygen within a chloroformate ester (ROCOCl) by sulfur can lead to a chlorothioformate (RSCOCl), a chlorothionoformate (ROCSCl), or a chlorodithioformate (RSCSCl). Phenyl chloroformate (PhOCOCl) reacts over the full range of solvents usually included in Grunwald-Winstein equation studies of solvolysis by an addition-elimination (A-E) pathway. At the other extreme, phenyl chlo...

Addition of Zinc Homoenolates to Acetylenic Esters and Amides : A Formal [ 3 + 21 Cycloaddition

The copper-catalyzed conjugate addition-cycloacylation reaction of zinc homoenolatee with acetylenic esters or acetylenic amides is described. The zinc homoenolate is prepared from [ (ethoxycyclopropy1)oxyltrimethylsilane and zinc chloride in ether. Addition of an acetylenic amide or ester provides 2-carboxamidoor 2-carboalkoxy-3-alkylcyclopent-2-en-l-ones ingood to excellent yields. The reacti...

Sulfur-containing compounds from Clinacanthus siamensis.

Two new sulfur-containing compounds, trans-3-methylsulfonyl-2-propenol (1) and trans-3-methylsulfinyl-2-propenol (2) were isolated together with trans-3-methylthioacrylamide (3), entadamide A (4) and entadamide C (5) from the leaves of Clinacanthus siamensis. The structures were established on the basis of the spectroscopic data. The compounds were tested for antimalarial and antimycobacterial ...