5-(Alkynyl)dibenzothiophenium Triflates: Sulfur-Based Reagents for Electrophilic Alkynylation
The synthesis of a series of 5-(alkynyl) dibenzothiophenium triflates, prepared from dibenzo[b,d]thiophene 5-oxide and the corresponding trimethylsilyl-substituted alkynes is reported. Their structures were determined by X-ray crystallography, and their reactivities as electrophilic alkynylation reagents evaluated. Their broad substrate scope and functional-group tolerance illustrate their potential to become an alternative to the broadly used EBX reagents. Isotope labeling studies reveal that alkynyldibenzothiophenium salts may undergo attack by nucleophiles at either the α- or β-carbon atom depending on the nature of their substitution pattern. Subsequent elimination of the dibenzothiophene unit and 1,2-migration of one of the groups (in case of β-attack) affords the desired alkynes.
Waldecker, Bernd,Kraft, Finn,Golz, Christopher,Alcarazo, Manuel
DIBENZOTHIOPHENE SALT AS ALKYNYLATING AND CYANATING AGENT
The present invention describes a new alkynylation and cyanation agent, as well as its preparation and use to introduce nitrile (cyano) or alkyne groups into chemical target molecules by means of an electrophilic reaction. To enable an electrophilic reaction, the chemical backbone of dibenzothiophene was used.
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Paragraph 0092; 0051
(2021/08/27)
Unsaturated thioacetic acids as novel mechanism-based inhibitors of peptidylglycine α-hydroxylating monooxygenase
Several unsaturated thioacetic acids were synthesized as potential mechanism-based inhibitors of peptidylglycine α-hydroxylating monooxygenase (PHM) prepared from horse serum. Trans-styrylthioacetic acid produced potent time-dependent inhibition of PHM. Potential mechanisms are proposed to explain PHM inactivation by unsaturated thioacetic acids.
Casara,Ganzhorn,Philippo,Chanal,Danzin
p. 393 - 396
(2007/10/03)
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