scholarly journals Lewis base-free thiophosphonium ion: a cationic sulfur atom transfer reagent

2021 ◽  
Author(s):  
Pawel Löwe ◽  
Tim Witteler ◽  
Fabian Dielmann
Keyword(s):  
Sulfur Atom ◽  
Lewis Base ◽  
Atom Transfer ◽  
Lawesson’S Reagent ◽  
Lawesson's Reagent

Phosphorus(V) sulfide and Lawesson’s reagent are commonly used thionating reagents which are considered to operate after dissociation into highly reactive dithiophosphorane fragments. We report the synthesis and properties of a...

Thionation of Aminophthalimide Hindered Carbonyl Groups and Application to the Synthesis of 3,6′-Dithionated Pomalidomides

Synlett ◽  
2021 ◽  
Author(s):  
Michael T. Scerba ◽  
Maxime A. Siegler ◽  
Nigel H. Greig
Keyword(s):  
Sulfur Atom ◽  
Late Stage ◽  
Carbonyl Groups ◽  
One Pot ◽  
Lawesson’S Reagent ◽  
Pyridine Complex ◽  
Lawesson's Reagent

AbstractHerein, we present a new one-pot procedure for the 3,6′-dithionation of pomalidomide derivatives in which the key 3-position sulfur atom is preferentially installed at the desired (but sterically congested) carbonyl of the aminophthalimide system and with regiochemistry distinct from Lawesson’s Reagent thionation methods. When heated in 1,4-dioxane with P4S10–pyridine complex, pomalidomides are smoothly and reproducibly converted into their 3,6′-dithionated analogues in roughly 30% isolated yield and at various scales. While detrimental to the desired 3,6′-type outcome when employing Lawesson’s Reagent, we hypothesize that the pomalidomide aniline group instead facilitates P4S10-type thionation at the otherwise hindered 3-position carbonyl, contributing to the selectivity observed. When paired with classical methods of thionation, this approach offers an interesting and appealing addition to the synthetic toolbox, permitting facile late-stage access to complementary thionated pomalidomides in direct single-flask procedures.

Thionation reactions of 2-pyrrole carboxylates

RSC Advances ◽  
2016 ◽  
Vol 6 (74) ◽  
pp. 69691-69697 ◽  
Author(s):  
Brandon R. Groves ◽  
Deborah A. Smithen ◽  
T. Stanley Cameron ◽  
Alison Thompson
Keyword(s):  
Elevated Temperatures ◽  
Lawesson’S Reagent ◽  
New Class ◽  
Lawesson's Reagent

Reaction of 2-pyrrole carboxylates with Lawesson's reagent at elevated temperatures results in the corresponding thionoesters, concurrent with the production of a new class of pyrrole annulated with the (1,3,2)-thiazaphospholidine unit.

Thioamide Derivative of the Potent Antitubercular 2-(Decylsulfonyl)acetamide is Less Active Against Mycobacterium tuberculosis, but a More Potent Antistaphylococcal Agent

2018 ◽  
Vol 71 (9) ◽  
pp. 716
Author(s):  
Hsien-Kuo Sun ◽  
Angel Pang ◽  
Dylan C. Farr ◽  
Tamim Mosaiab ◽  
Warwick J. Britton ◽  
...  
Keyword(s):  
Staphylococcus Aureus ◽  
Mycobacterium Tuberculosis ◽  
Parent Compound ◽  
Gram Positive ◽  
Antibacterial Compounds ◽  
Lawesson’S Reagent ◽  
Lawesson's Reagent ◽  
Structural Simplicity

Due to the prevalence of thioamides in antibacterial compounds, we chose to convert the amide in the antitubercular compound 2-(decylsulfonyl)acetamide to a thioamide using Lawesson’s reagent to study its activity against a range of microorganisms. This derivative (8) had significantly diminished activity against tuberculosis but slightly better activity than the parent compound against the Gram positive species Staphylococcus aureus. This activity against a second major pathogen is remarkable considering the structural simplicity of these compounds.

Metal–Ligand Cooperativity Promoting Sulfur Atom Transfer in Ferrous Complexes and Isolation of a Sulfurmethylenephosphorane Adduct

2018 ◽  
Vol 57 (18) ◽  
pp. 11552-11559 ◽  
Author(s):  
Dieter Sorsche ◽  
Matthias E. Miehlich ◽  
Eva M. Zolnhofer ◽  
Patrick J. Carroll ◽  
Karsten Meyer ◽  
...  
Keyword(s):  
Sulfur Atom ◽  
Atom Transfer ◽  
Metal Ligand
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