A comprehensive survey upon diverse and prolific applications of chitosan-based catalytic systems in one-pot multi-component synthesis of heterocyclic rings

International Journal of Biological Macromolecules, Journal Year: 2021, Volume and Issue: 186, P. 1003 - 1166

Published: June 24, 2021

Language: Английский

---

Copper-Catalyzed One-Pot Synthesis of Thiazolidin-2-imines

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(11), P. 7727 - 7740

Published: May 10, 2024

The synthesis of thiazolines, thiazolidines, and thiazolidinones has been extensively studied, due to their biological activity related neurodegenerative diseases, such as Parkinson's Alzheimer's, well antiparasitic antihypertensive properties. closely thiazolidin-2-imines have studied less, efficient strategies for synthesizing them, mainly based on the reaction propargylamines with isothiocyanates, explored less. use one-pot approaches, providing modular, straightforward, sustainable access these compounds, also received very little attention. Herein, we report a novel, one-pot, multicomponent, copper-catalyzed among primary amines, ketones, terminal alkynes, toward bearing quaternary carbon centers five-membered ring, in good excellent yields. Density functional theory calculations, combined experimental mechanistic findings, suggest that copper(I)-catalyzed between situ-formed isothiocyanates proceeds lower energy barrier pathway leading S-cyclized product, compared N-cyclized one, chemo- regioselective formation 5-exo-dig thiazolidin-2-imines.

Language: Английский

---

An Efficient One-Pot Synthesis of 5-Sulfanyl-1-[2-(vinyloxy)ethyl]-1H-pyrrol-2-amines as Precursors of 1-Vinylpyrroles

Synthesis, Journal Year: 2022, Volume and Issue: 54(18), P. 4033 - 4048

Published: April 7, 2022

Abstract Sequential processing of monolithiated tertiary propargylamines with 2-(vinyloxy)ethyl isothiocyanate and t-BuOK–DMSO results in the introduction a highly reactive group at position 1 pyrrole ring thus formed. In this way, series new 5-sulfanyl-1-[2-(vinyloxy)ethyl]-1H-pyrrol-2-amines were obtained yield up to 92%. The latter presence system (110–120 °C, 10–15 min) eliminates vinyl alcohol give rare-functionalized 1-vinylpyrroles, namely 5-sulfanyl-1-vinyl-1H-pyrrol-2-amines, inaccessible by known methods.

Language: Английский

---

Dinuclear silver-bis(N-heterocyclic carbene) complexes: Synthesis, catalytic activity in propargylamine formation and computational studies

Journal of Coordination Chemistry, Journal Year: 2021, Volume and Issue: 74(14), P. 2289 - 2301

Published: July 18, 2021

Preparation of a series 1,1′-dialkyl-3,3′-(2-methylenepropane-1,3-diyl)dibenzimidazolium salts (alkyl = ethyl, propyl, butyl) (2a-2c) and their dinuclear bis(N-heterocyclic carbene) silver complexes (3a-3c) is reported. The were synthesized via in situ deprotonation with Ag2O 67-74% yields. structural definitions the compounds performed by 1H NMR, 13C elemental analysis, FT-IR also LC-MSMS techniques (only for 3a-3c). utilized three-component coupling reactions aldehydes, amines alkynes (A3-coupling). It was found that increasing chain length alkyl substituent on N-heterocyclic carbene ligand led to increase catalytic performance. 3c showed highest activity 81% yield TON 27 N,N-diethyl-3-phenylprop-2-yn-1-amine formation. Geometry optimization geometric parameters calculated compounds. theoretical harmonic vibration frequencies molecules computed DFT/B3LYP methods optimized geometries.

Language: Английский

---

Mass Spectra of New Heterocycles: XXVI. Electron Impact Ionization Study of N-(5-Amino­thiophen-2-yl)- and N-[2-(Methylsulfanyl)-1,3-thiazol-5-yl]­isothioureas

Russian Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 59(7), P. 1136 - 1143

Published: July 1, 2023

Language: Английский

---

Self-Assembly of 4,4′-Linked Dipyrromethanes from Unconventional Reactants─Propargylamines, 2-(Vinyloxy)ethyl Isothiocyanate, and Alkylating Agents under Basic Conditions

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 89(2), P. 864 - 881

Published: Dec. 28, 2023

Self-assembly of 4,4′-linked dipyrromethanes from 2-(vinyloxy)ethyl isothiocyanate, tertiary propargylamines, and alkylating agents has been discovered. The plausible reaction mechanism, the major stages which have confirmed experimentally, includes (1) lithiation propargylamine (with n-BuLi); (2) formation lithium N-[2-(vinyloxy)ethyl]but-2-ynimidothioate (product addition monolithiated to isothiocyanate); (3) isomerization latter in corresponding allenylimidothioate (under action t-BuOK/t-BuOH system); (4) low-temperature (<15 °C) intramolecular cyclization into potassium N-(5-amino-2-thienyl)-N-[2-(vinyloxy)ethyl]amide; (5) base-induced cleavage C–O bond N-[2-(vinyloxy)ethyl] group removal vinyloxide-anion leading acetaldehyde; (6) interaction acetaldehyde with two molecules N-(5-amino-2-thienyl)-N-[2-(vinyloxy)ethyl]amide-anion resulting dithienomethane N-anionic intermediate; (7) recyclization dipyrromethane S-anionic intermediate. Final S-alkylation affords synthetically challenging 4,4′-dipyrromethanes a yield 22–51%. whole process is carried out single synthetic operation very short time (∼10–15 min, excluding alkylation time).

Language: Английский

---

Mass Spectra of New Heterocycles: XXIII. Electron Impact and Chemical Ionization Study of 5-[(Cyanomethyl)sulfanyl]- and 5-[(1,3-Dioxolan-2-ylmethyl)sulfanyl]-1H-pyrrol-2-amines

Russian Journal of Organic Chemistry, Journal Year: 2021, Volume and Issue: 57(12), P. 1901 - 1912

Published: Dec. 1, 2021

Language: Английский

---

Mass Spectra of New Heterocycles: XXII. Electron Impact and Chemical Ionization of 1-Alkyl(cycloalkyl, alkoxyalkyl)-5-[(alkyl, allyl, benzyl)sulfanyl]-1H-pyrrol-2-amines

Russian Journal of Organic Chemistry, Journal Year: 2021, Volume and Issue: 57(3), P. 347 - 354

Published: March 1, 2021

Language: Английский

---

Reactions of Acetylenic and Allenic Carbanions with Heterocumulenes: A Straightforward Route to Fundamental Heterocycles

Russian Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 59(10), P. 1676 - 1703

Published: Oct. 1, 2023

Language: Английский

---

Acetylenic and allenic carbanions in the reaction with heterocumulenes: a simple way to fundamental heterocycles

Журнал органической химии, Journal Year: 2023, Volume and Issue: 59(10), P. 1319 - 1350

Published: Dec. 15, 2023

Language: Английский

---