Synthesis of Isothiocyanates from Primary Amines via Visible-Light Photocatalysis

Organic Letters, Journal Year: 2023, Volume and Issue: 25(30), P. 5692 - 5696

Published: July 26, 2023

A photocatalyzed, efficient, and mild approach for the synthesis of various substituted isothiocyanates from amine carbon disulfide was reported in this work. This expands scope photocatalytic applications provides a new method preparation aliphatic aromatic isothiocyanates, which are significant organic building blocks biological diagnostic markers.

Language: Английский

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Engineering of Dual-Function Vitreoscilla Hemoglobin: A One-Pot Strategy for the Synthesis of Unnatural α-Amino Acids

Organic Letters, Journal Year: 2023, Volume and Issue: 25(39), P. 7115 - 7119

Published: Sept. 22, 2023

Despite a well-developed and growing body of work on the directed evolution hemoproteins, potential hemoproteins to catalyze non-natural reactions remains underexplored. This paper reports new biocatalytic strategy for one-pot synthesis unnatural α-amino acids. Engineered variants dual-function Vitreoscilla hemoglobin were found efficiently N-H insertion C-H sp3 alkylation, providing moderate excellent yields (57%-95%) acid derivatives turnover numbers (1425-2375).

Language: Английский

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Radical-Cascade Avenue to Access 1,2-Dithioles Employing Dithioesters and Edman’s Reagent

Organic Letters, Journal Year: 2023, Volume and Issue: 25(13), P. 2258 - 2263

Published: March 26, 2023

An operationally simple and efficient domino etiquette has been developed for the facile construction of 1,2-dithioles employing easily accessible dithioesters as a three-atom CCS synthon aryl isothiocyanates two-atom CS unit in absence any catalyst additive at room temperature under open air. The reaction proceeded efficiently affording desired good yields having various functional groups diverse electronic steric nature. This approach avoids possible toxicity tiresome workup conditions features easy to handle, cheap, readily reagents, O2 green oxidant, gram-scale ability. Notably, final S-S bond formation cascade ring follow radical pathway, which recognized via trapping experiment with BHT during course reaction. exocyclic C═N position 3 1,2-dithiole possesses Z stereochemistry.

Language: Английский

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Lipase‐Catalyzed Synthesis of Anthrone Functionalized Benzylic Amines via a Multicomponent Reaction in Supercritical Carbon Dioxide

ChemistrySelect, Journal Year: 2022, Volume and Issue: 7(5)

Published: Feb. 2, 2022

Abstract In this study, supercritical carbon dioxide (ScCO 2 ), which is a sustainable and green solvent, was used as reaction medium in the lipase‐catalyzed synthesis of anthrone‐functionalized benzylic amines for first time. We synthesized target compounds via multicomponent cascade aldehydes, sulfonamides, anthrones ScCO . The can be accomplished good‐to‐excellent yields (77 %–95 %) exhibit good functional group tolerance. brief, characterized by step economy, metal‐free conditions, environmentally friendly solvents, biocatalysts.

Language: Английский

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Efficient synthesis of 3-hydroxy chromones via oxidative cyclization mediated by lipase

Green Chemistry Letters and Reviews, Journal Year: 2022, Volume and Issue: 15(3), P. 689 - 694

Published: July 3, 2022

In this work, an efficient synthesis of 3-hydroxy chromones was accomplished through oxidative cyclization mediated by lipase. This enzymatic process has salient features environmental friendliness, mild reaction condition, satisfactory yield, green reusable biocatalyst, and short time. The proposed method expands the application lipase in organic synthesis.

Language: Английский

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Phenolate‐Induced N−O Bond Formation versus Tiemann‐Type Rearrangement for the Synthesis of 3‐Aminobenzisoxazoles and 2‐Aminobenzoxazoles

ChemistryOpen, Journal Year: 2022, Volume and Issue: 11(12)

Published: Dec. 1, 2022

Abstract A novel oxadiazolone‐based method for the synthesis of 3‐aminobenzisoxazoles by N−O bond formation and 2‐aminobenzoxazoles through a Tiemann‐type rearrangement has been developed. The these two pharmaceutically relevant heterocycles was realized an unexplored retrosynthetic disconnection using cyclic nitrenoid precursor‐based strategy. selective isomers significantly influenced steric electronic effects substituents. However, tetrabutylammonium chloride (TBACl) efficiently promoted over formation. Control experiments indicate that deprotonation phenol induces both rearrangements.

Language: Английский

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Synthesis of functionalized 1,4-dihydropyridines containing benzosultams catalyzed by lipase

New Journal of Chemistry, Journal Year: 2023, Volume and Issue: 47(20), P. 9708 - 9713

Published: Jan. 1, 2023

As a base structural unit, 1,4-dihydropyridines (DHPs) containing benzosultams widely exist in bioactive molecules and drugs.

Language: Английский

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Oxidative cyclization of N-(2-oxo-4-phenyl-1,2-dihydropyridin-3-yl)thioureas to 7-phenyloxazolo[5,4-b]pyridin-2-amines

Russian Chemical Bulletin, Journal Year: 2024, Volume and Issue: 73(7), P. 2004 - 2013

Published: July 1, 2024

Language: Английский

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Hemin-catalyzed controlled oxidative cyanation of secondary amine for the synthesis of α-aminonitriles and α-iminonitriles

Molecular Catalysis, Journal Year: 2022, Volume and Issue: 529, P. 112576 - 112576

Published: Aug. 1, 2022

Language: Английский

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Efficient synthesis of 2-aryl benzothiazoles mediated by Vitreoscilla hemoglobin

Molecular Catalysis, Journal Year: 2022, Volume and Issue: 533, P. 112784 - 112784

Published: Nov. 4, 2022

Language: Английский

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