Thoination of N-alkyl-O-acyl hydroxamic acid derivatives via Lawesson's reagent

Thionation reactions of 2-pyrrole carboxylates

RSC Advances ◽

10.1039/c6ra14809c ◽

2016 ◽

Vol 6 (74) ◽

pp. 69691-69697 ◽

Cited By ~ 4

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.

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Cross metathesis-mediated synthesis of hydroxamic acid derivatives

Beilstein Journal of Organic Chemistry ◽

10.3762/bjoc.14.285 ◽

2018 ◽

Vol 14 ◽

pp. 3070-3075 ◽

Cited By ~ 4

Author(s):

Shital Kumar Chattopadhyay ◽

Subhankar Ghosh ◽

Suman Sil

Keyword(s):

Hydroxamic Acid ◽

Cyclic Peptide ◽

Alternative Synthesis ◽

Acid Component ◽

Cross Metathesis ◽

Reaction Proceeds ◽

Amino Acid Component ◽

Short Time ◽

Unusual Amino Acid ◽

Hydroxamic Acid Derivatives

An alternative synthesis of α,ß-unsaturated hydroxamates via cross metathesis between a class-I olefin and N-benzyloxyacrylamide is reported. The reaction proceeds better in the presence of Grubbs’ second generation catalyst within short time and in good yields (57–85%) with a range of substrates. Subsequent hydrogenation of each of the CM products delivers the title compounds in moderate to very good yield (70–89%). An important demonstration of the protocol is the preparation of the unusual amino acid component of the bioactive cyclic peptide Chap-31.

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

Australian Journal of Chemistry ◽

10.1071/ch18206 ◽

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.

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