A metal-free and a solvent-free synthesis of thio-amides and amides: an efficient Friedel–Crafts arylation of isothiocyanates and isocyanates

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Abstract

A rapid, metal-free and solvent-free (very low loading of solvent in few cases) reaction conditions for synthesizing thioamides and amides using a Bronsted super acid such as triflic acid has been developed. This method shows a broad substrate scope with a variety of electron-rich arenes including thiophene derivatives. The reaction works well for both aromatic as well as aliphatic isothiocyanates. Most of the thioamides are obtained in excellent yields in short reaction times and in most of the examples, a simple work up procedure has been developed which does not require further purification.

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Mechanism of thioamide drug action against tuberculosis and leprosy

Feng Wang, ROBERT LANGLEY, Gulcin Gulten … (2007)

Thioamide drugs, ethionamide (ETH) and prothionamide (PTH), are clinically effective in the treatment of Mycobacterium tuberculosis, M. leprae, and M. avium complex infections. Although generally considered second-line drugs for tuberculosis, their use has increased considerably as the number of multidrug resistant and extensively drug resistant tuberculosis cases continues to rise. Despite the widespread use of thioamide drugs to treat tuberculosis and leprosy, their precise mechanisms of action remain unknown. Using a cell-based activation method, we now have definitive evidence that both thioamides form covalent adducts with nicotinamide adenine dinucleotide (NAD) and that these adducts are tight-binding inhibitors of M. tuberculosis and M. leprae InhA. The crystal structures of the inhibited M. leprae and M. tuberculosis InhA complexes provide the molecular details of target–drug interactions. The purified ETH-NAD and PTH-NAD adducts both showed nanomolar Kis against M. tuberculosis and M. leprae InhA. Knowledge of the precise structures and mechanisms of action of these drugs provides insights into designing new drugs that can overcome drug resistance.

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Use of Lawesson's reagent in organic syntheses.

O Mert, T Öztürk, Ibrahim Ertas (2007)

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Closthioamide: an unprecedented polythioamide antibiotic from the strictly anaerobic bacterium Clostridium cellulolyticum.

Swantje Behnken, T Lincke, Keishi Ishida … (2010)

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Author and article information

Journal

Journal ID (publisher-id): RSCACL

Title: RSC Adv.

Abbreviated Title: RSC Adv.

Publisher: Royal Society of Chemistry (RSC)

ISSN (Electronic): 2046-2069

Publication date Created: 2014

Publication date (Print): 2014

Volume: 4

Issue: 105

Pages: 60798-60807

Article

DOI: 10.1039/C4RA12944J

SO-VID: e0ce4a3d-09fb-48f4-87ea-b4b2f6fabd49

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