Rongalite as C1 Synthon in the Synthesis of Divergent Pyridines and Quinolines

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(11), С. 7188 - 7198

Опубликована: Май 12, 2023

Rongalite has been used as a cheap and efficient carbon synthon for the synthesis of divergent N-heteroaromatics, including different pyridines quinolines. The selective products can be achieved by employing enaminones or enaminones/anilines reaction partners. In addition, compared with using conventional aldehyde synthons, rongalite displays an evident advantage in providing considerably higher product yields under milder conditions. GC-MS analysis process performed to probe possible mechanism.

Язык: Английский

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Oxidative Dehydrogenative Coupling of Arylamines with N-allyl and N-vinylamines for the Synthesis of Quinolines and 2-Methylquinoline Derivatives

Tetrahedron, Год журнала: 2025, Номер unknown, С. 134450 - 134450

Опубликована: Янв. 1, 2025

Язык: Английский

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Formaldehyde surrogates in multicomponent reactions

Beilstein Journal of Organic Chemistry, Год журнала: 2025, Номер 21, С. 564 - 595

Опубликована: Март 13, 2025

Formaldehyde emerges as a cornerstone in multicomponent reactions, mainly prized for its robust reactivity. Yet, alongside these beneficial traits, this highly reactive C1-building block raises concerns, primarily regarding toxicity. One notable issue is the challenge of controlling formation undesired byproducts during reactions. This review explores alternative blocks that serve surrogates formaldehyde, aiming to mitigate some challenges associated with use By identifying alternatives, toxicity concerns and improved reaction control can be addressed, paving way more efficient sustainable synthetic methodologies.

Язык: Английский

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Recent Achievements in Organic Reactions in DMSO

Опубликована: Март 8, 2024

In this chapter, we have summarized some special and representative transformations using DMSO as a green solvent in organic synthesis over the last 5 years. contrast to previous reviews, focus more on situ activation pattern of by summarizing different fragmentation processes show reaction initiation pathway. For example, Pummerer-type, Selectfluor-enabled, electrocatalytic-enabled, photocatalytic-enable were classified discussed detail. each pattern, several recent are listed, along with their selected products generality, while detailed mechanism is also provided after example facilitate reader's understanding illustrate chemical principles. We believe that chapter provides unique perspective lead better DMSO-mediated integrated information for researchers who keen select method activation.

Язык: Английский

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Facile access to 3-sulfonylquinolines via Knoevenagel condensation/aza-Wittig reaction cascade involving ortho-azidobenzaldehydes and β-ketosulfonamides and sulfones

Beilstein Journal of Organic Chemistry, Год журнала: 2023, Номер 19, С. 800 - 807

Опубликована: Июнь 9, 2023

Quinoline-based sulfonyl derivatives, and especially sulfonamides, are relevant promising structures for drug design. We have developed a new convenient protocol the synthesis of 3-sulfonyl-substituted quinolines (sulfonamides sulfones). The approach is based on Knoevenagel condensation/aza-Wittig reaction cascade involving o-azidobenzaldehydes ketosulfonamides or ketosulfones as key building blocks. appropriate both ketosulfonyl reagents α-sulfonyl-substituted alkyl acetates providing target quinoline derivatives in good to excellent yields.

Язык: Английский

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Acid/base-co-catalyzed cyclization of ketones with o-amino-benzylamines: Direct synthesis of quinoline compounds

Tetrahedron Letters, Год журнала: 2023, Номер 128, С. 154700 - 154700

Опубликована: Авг. 10, 2023

Язык: Английский

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Facile Cleavage of Activated Ketones: An Access to Thioethers via In Situ Generation of Anhydrides by Pummerer-Type Rearrangement

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(10), С. 7020 - 7026

Опубликована: Апрель 25, 2024

Herein, we report an oxygen insertion in activated ketones from simple inorganic carbonates for the synthesis of symmetric aromatic anhydrides. For first time, Li2CO3 acts as source and situ generated anhydrides undergo Pummerer-type rearrangement to access α-benzoyloxy–thioethers. Attractively, this protocol occurs under metal-, ligand-, oxidant-free conditions is compatible with a wide range substrates. Control experiments reveal reaction pathway.

Язык: Английский

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Electrochemical Selenocyclization of N-Alkyl anilines: Access to 3-Selenyl quinolines

Tetrahedron, Год журнала: 2024, Номер unknown, С. 134257 - 134257

Опубликована: Сен. 1, 2024

Язык: Английский

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Recent advances in the synthesis of N-heterocycles from α-amino acids mediated by iodine

Chemical Communications, Год журнала: 2024, Номер unknown

Опубликована: Янв. 1, 2024

The synthesis of N-heterocycles has received extensive attention from scientists considering their important role in organic synthesis, pharmaceuticals, and materials chemistry. α-Amino acids (α-AAs), both natural non-natural, are structurally diverse, containing basic amino groups, acidic carboxyl various side-chain R groups a single molecule. Given structural properties wide range sources, they have undoubtedly become suitable synthetic building blocks for synthesis. However, conventional transformations (AAs) focus on the independently. Conversions these two prominent functional generally do not affect alpha positions branched chains. Over past decade, with application iodine (I

Язык: Английский

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Dual Functionalization of the α,β-C–H Bonds in Alanine Ester Derivatives via Enamine–Imine Tautomerism: Construction of 4-Quinolinolate Skeletons through a Fragmentation–Reassembly Pathway

Organic Letters, Год журнала: 2024, Номер unknown

Опубликована: Дек. 16, 2024

Using a SbCl

Язык: Английский

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