Intramolecular Reductive Amidation of Unactivated Esters with Nitroarenes: A Telescoped Synthesis of Tetrahydropyrrolo/Pyrido[1,2-a]quinoxalinones DOI
Amitava Hazra, Joydev K. Laha

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(15), С. 11053 - 11059

Опубликована: Июль 22, 2024

A reductive amidation of unactivated esters with nitroarenes, a key step in the telescopic synthesis tetrahydropyrrolo[1,2-

Язык: Английский

Reducing the cost of making drugs for low/limited-income countries by going green DOI Creative Commons
Bruce H. Lipshutz

Trends in Chemistry, Год журнала: 2024, Номер 6(4), С. 173 - 185

Опубликована: Март 28, 2024

In efforts to improve the affordability of drugs in regions world where they are most needed, synthetic sequences described that apply green and sustainable technologies partial or total syntheses several target molecules. Here, focus is on routes to: (i) three antimalarial drugs, key portions thereof; (ii) a targeted polypeptide (as found Paxlovid) used extensively treatment COVID-19; (iii) two subsections potent, timely, anti-HIV agent. Each highlighted by its adherence Principles Green Chemistry, leading more environmentally responsible, hence potentially cost-effective, route associated with their manufacture. Such approaches may impact health well-being millions, while dramatically reducing overall environmental impact.

Язык: Английский

Процитировано

2

Photochemical Deracemization of N‐Carboxyanhydrides en route to Chiral α‐Amino Acid Derivatives DOI Creative Commons
Maximilian Iglhaut,

Philip Freund,

Thorsten Bach

и другие.

Angewandte Chemie International Edition, Год журнала: 2024, Номер unknown

Опубликована: Окт. 16, 2024

Readily accessible, racemic N-carboxyanhydrides (NCAs) of α-amino acids underwent a deracemization reaction upon irradiation at λ=366 nm in the presence chiral benzophenone catalyst. The enantioenriched NCAs (up to 98 % ee) serve as activated acid surrogates and, due their instability, they were directly converted into consecutive products. N-Protected esters obtained after with MeOH and N-benzoylation (14 examples, 70 %-quant., 82-96 ee). Other reactions included amide (ten 65 90-98 peptide (three 75-89 %, d. r.=97/3 94/6) bond formation. Limitations method relate for some issues solubility, photooxidation, high configurational lability.

Язык: Английский

Процитировано

2

Metal-Free Bisamidation of N-Tosylhydrazones with Carboxylic Acids Promoted by Tetrabutylammonium Iodide and tert-Butyl Hydroperoxide DOI
Ali Shamnad,

Kalinga H. Nayak,

Beneesh P. Babu

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(9), С. 6545 - 6554

Опубликована: Апрель 17, 2024

A versatile reaction between N-tosylhydrazones and carboxylic acids to access bisamides is reported. This metal-free, room-temperature was catalyzed by TBAI, while TBHP served as the oxidant. Broad substrate scope good functional group tolerance are key features of strategy. Subsequent intramolecular N-arylation suitably substituted readily afforded functionalized 3-indazolones.

Язык: Английский

Процитировано

1

Covalent Organic Framework Catalyzed Amide Synthesis Directly from Alcohol Under Red Light Excitation DOI

Monojit Roy,

Bikash Mishra,

Shyamali Maji

и другие.

Angewandte Chemie, Год журнала: 2024, Номер 136(40)

Опубликована: Июль 2, 2024

Abstract The dehydrogenative coupling of alcohols and amines to form amide bonds is typically catalysed by homogeneous transition metal catalysts at high temperatures ranging from 130–140 °C. In our pursuit an efficient recyclable photocatalyst capable conducting this transformation room temperature, we report herein a COF‐mediated synthesis. TTT‐DHTD COF was strategically designed incorporate density functional units, specifically dithiophenedione, trap photogenerated electrons effectively facilitate hydrogen atom abstraction reactions. photoactive COF, synthesized using solvothermal methods showed crystallinity moderate surface area, providing ideal platform for heterogeneous Light absorption the across entire visible range, narrow band gap, valence position make it well‐suited generation excitons necessary targeted dehydrogenation. Utilizing red light irradiation employing extremely low loading have successfully prepared wide range amides, including challenging secondary in good excellent yields. substrates’ group tolerance, very mild reaction conditions, catalyst's significant recyclability represent substantial advancements over prior methodologies.

Язык: Английский

Процитировано

1

Intramolecular Reductive Amidation of Unactivated Esters with Nitroarenes: A Telescoped Synthesis of Tetrahydropyrrolo/Pyrido[1,2-a]quinoxalinones DOI
Amitava Hazra, Joydev K. Laha

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(15), С. 11053 - 11059

Опубликована: Июль 22, 2024

A reductive amidation of unactivated esters with nitroarenes, a key step in the telescopic synthesis tetrahydropyrrolo[1,2-

Язык: Английский

Процитировано

1