Recent Advances in the Use of Dimethyl Sulfoxide as a Synthon in Organic Chemistry

Topics in Current Chemistry, Год журнала: 2022, Номер 380(6)

Опубликована: Окт. 28, 2022

Язык: Английский

---

I₂-DMSO-Mediated Construction of 2,3- and 2,4-Disubstituted Pyrimido[1,2-b]indazole Skeletons

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(6), С. 3941 - 3953

Опубликована: Фев. 29, 2024

An efficient synthetic method for constructing 2,3- and 2,4-disubstituted pyrimidio[1,2-b]indazole skeletons through I2-DMSO-mediated substrate-controlled regioselective [4 + 2] cyclization is reported. The reaction conditions are mild, its operation simple, the substrate scope wide. More than 60 derivatives have been synthesized, providing a new methodology related molecules potentially enriching bioactive-molecule libraries.

Язык: Английский

---

Cooperation between Cu+ and Cu2+ species in CuCoAl layered double hydroxide and substrate promoting effect afford a really simple protocol for the efficient synthesis of quinazolines

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер 22(22), С. 4494 - 4501

Опубликована: Янв. 1, 2024

In this study, a really simple and efficient catalytic protocol for the construction of quinazolines from alcohol diamine has been developed based on CuCoAl layered double hydroxide (CuCoAl-LDH). The CuCoAl-LDH catalyst could accelerate cascade reactions without any additives tolerate various alcohols with satisfactory yields. Cooperation between Cu

Язык: Английский

---

Research progress of self-organized reaction networks for cascade reactions

Tetrahedron, Год журнала: 2024, Номер 166, С. 134210 - 134210

Опубликована: Авг. 27, 2024

Язык: Английский

---

Recent Advances in DMSO-Based Direct Synthesis of Heterocycles

Molecules, Год журнала: 2022, Номер 27(23), С. 8480 - 8480

Опубликована: Дек. 2, 2022

Besides serving as a low-toxicity, inexpensive and easily accessible solvent, dimethyl sulfoxide (DMSO) has also been extensively used versatile reagent for the synthesis of functionalized molecules. Dimethyl can not only be utilized carbon source, sulfur source an oxygen but employed crucial oxidant enabling various transformations. The past decade witnessed large number impressive achievements on direct heterocycles well modifications heterocyclic compounds by applying DMSO reagent. This review summarized DMSO-based heterocycle constructions from 2012 to 2022.

Язык: Английский

---

A Pummerer Reaction-Enabled Modular Synthesis of Alkyl Quinoline-3-carboxylates and 3-Arylquinolines from Amino Acids

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(6), С. 3760 - 3771

Опубликована: Фев. 23, 2023

Concise synthesis of functionalized quinolines has received continuous research attention owing to the biological importance and synthetic potential bicyclic N-heterocycles. However, routes 2,4-unsubstituted alkyl quinoline-3-carboxylate scaffold, which is an important motif in drug design, remain surprisingly limited, with modular protocols that proceed from readily available materials being even more so. We herein report acidic I2-DMSO system converts aspartates anilines into quinoline-3-carboxylate. This method can be extended a straightforward 3-arylquinolines by simply replacing phenylalanines. Mechanistic studies revealed DMSO was activated HI via Pummerer reaction provide C1 synthon, while amino acid catabolized C2 synthon through I2-mediated Strecker degradation. A formal [3 + 2 1] annulation these two concurrently generated synthons aniline responsible for selective formation quinoline core. The utility this protocol illustrated efficient human 5-HT4 receptor ligand. Moreover, unprecedented chemoselective 2-deuterated, 3-substituted quinoline, featuring reaction, been established.

Язык: Английский

---

Oxidative annulation of l-phenylalanine using I₂/DMSO: an easy approach for chemoselective synthesis of 2,3,5-trisubstituted pyridines and 2,5-disubstituted oxazoles

Organic & Biomolecular Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

A facile approach for chemoselective synthesis of 2,3,5-trisubstituted pyridines and 2,5-disubstituted oxazoles from l -phenylalanine aryl methyl ketone using I 2 /DMSO has been developed.

Язык: Английский

---

A Novel Fe(III) Complex of Bispicen Ligand Covalently Attached to an Fe₃O₄ Nanomagnet: Catalytic Properties in C‐H Oxidation and Benzoxazol Synthesis

Applied Organometallic Chemistry, Год журнала: 2025, Номер 39(6)

Опубликована: Май 2, 2025

ABSTRACT This study discusses the development of an effective and environmentally friendly C‐H oxidation process for creation oxygenated compounds in presence tert ‐butyl hydroperoxide by a magnetically recoverable Fe 3 O 4 @SiO 2 ‐FeL Bpn nanocomposite. L stands deprotonated, pyridine‐based, four‐dentate, bispicen ligand. The synthesised catalyst was characterised Fourier‐transform infrared spectroscopy (FTIR), energy‐dispersive X‐ray analysis (EDX), diffraction (XRD), photoelectron (XPS), field emission scanning electron microscopy (FESEM), transmission (FETEM), dynamic light scattering (DLS), thermal gravimetric (TGA), vibrating sample magnetometer (VSM). (40 mg) introduced as TBHP (4 eq) varied C–H bonds to related carbonyl high yields. (5 used synthesis benzoxazole derivatives from 1 mmol every substrate aldehydes, ammonium acetate, catechol. By this process, vast amounts benzoxazoles were satisfyingly obtained H under moderated situations, whole products gained with excellent results. recovered reaction environment through simple exterior magnet reused three times without any remarkable reactivity loss. Moreover, hot filtration test confirmed heterogeneous character catalyst.

Язык: Английский

---

Application of N,N-Dimethylethanolamine as a One-Carbon Synthon for the Synthesis of Pyrrolo[1,2-a]quinoxalines, Quinazolin-4-ones, and Benzo[4,5]imidazoquinazolines via [5 + 1] Annulation

The Journal of Organic Chemistry, Год журнала: 2022, Номер 87(21), С. 14753 - 14762

Опубликована: Окт. 18, 2022

The synthesis of N-heterocycles composes a significant part synthetic chemistry. In this report, Cu(II)-catalyzed green and efficient pyrrolo[1,2-a]quinoxaline, quinazolin-4-one, benzo[4,5]imidazoquinazoline derivatives was developed, employing N,N-dimethylethanolamine (DMEA) as C1 synthon. Green oxidant O2 is critical in these transformations, facilitating the formation key intermediate─a reactive iminium ion. method conducted under mild conditions compatible with diversity functional groups, providing an appealing alternative to previously developed protocols.

Язык: Английский

---

I₂-DMSO Promoted Deaminative Coupling Reactions of Glycine Esters: Access to 5-(Methylthio)pyridazin-3(2H)-ones

Organic Letters, Год журнала: 2023, Номер 25(14), С. 2382 - 2387

Опубликована: Март 31, 2023

An unprecedented, one-step strategy for the synthesis of 5-(methylthio)pyridazin-3(2H)-one derivatives has been developed through iodine triggered deaminative coupling glycine esters with methyl ketones and hydrazine hydrate in DMSO. These transformations absence helped to generate different 3-methylthio-4-oxo-enoates good yields. Notably, DMSO played multiple roles such as oxidant, methylthiolating reagent, solvent.

Язык: Английский

---