Traceless solid-phase synthesis of multiple sulfonamide-containing cyclic sulfides exploiting microwave irradiation

Saruta, Kunio; Ogiku, Tsuyoshi; Fukase, Koichi

doi:10.1016/j.tetlet.2009.05.028

Cited by 10 publications

(6 citation statements)

References 16 publications

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“…4‐Tosylthiomorpholine (3g): 20 White solid. 1 H NMR (400 MHz, CDCl 3 ): δ = 7.60 (d, J = 8.2 Hz, 2 H), 7.30 (d, J = 8.0 Hz, 2 H), 3.31–3.28 (m, 4 H), 2.69–2.67 (m, 4 H), 2.42 (s, 3 H) ppm.…”

Section: Methodsmentioning

confidence: 99%

Iodine‐Catalyzed Oxidative Amination of Sodium Sulfinates: A Convenient Approach to the Synthesis of Sulfonamides under Mild Conditions

2015

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The iodine‐catalyzed oxidative amination of sodium sulfinates in the presence of sodium percarbonate as the oxidant has been developed. The reaction shows good substrate scope and tolerates a wide range of functionalities in both amine and sodium sulfinate substrates. Aliphatic amines, heteroaromatic amines and hydrochloride salts of amines can be employed as the amine sources in this transformation. Mechanistic studies indicated that a radical pathway might be involved in the reaction process. This transition‐metal‐free protocol offers an alternative and convenient approach for a preparation of a series of sulfonamides in moderate to good yields under mild conditions.

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Section: Methodsmentioning

confidence: 99%

Iodine‐Catalyzed Oxidative Amination of Sodium Sulfinates: A Convenient Approach to the Synthesis of Sulfonamides under Mild Conditions

2015

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“…The same methodology was also applied for the synthesis of sulfonamide-containing cyclic sulfides. 326 As in the previous case, the synthesis started with the replacement of the chlorine of Merrifield resin 1 with 2-mercaptoethanols 1173 to yield resin 1174 (Scheme 213). Subsequent treatment with N-Boc- protected sulfonamides 1175 under Fukuyama-modified Mitsunobu conditions 203 converted the alcohols to the sulfonamides, and the Boc-protecting group was then cleaved by n-BuNH 2 (resin 1176).…”

Section: Chemical Reviewsmentioning

confidence: 99%

“…This section describes traceless synthetic strategies involving on-resin intramolecular cyclization that resulted in the formation of quaternary ammonium, , sulfonium, , or oxonium salts that activated the linker for cleavage. For example, in the case of ammonium salts, the products are released from the resin by treatment with a nucleophile (scenario A, Scheme ).…”

Section: Release From Onium Speciesmentioning

confidence: 99%

Traceless Solid-Phase Organic Synthesis

2019

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Traceless solid-phase synthesis represents an ultimate sophisticated synthetic strategy on insoluble supports. Compounds synthesized on solid supports can be released without a trace of the linker that was used to tether the intermediates during the synthesis. Thus, the target products are composed only of the components (atoms, functional groups) inherent to the target core structure. A wide variety of synthetic strategies have been developed to prepare products in a traceless manner, and this review is dedicated to all aspects of traceless solid-phase organic synthesis. Importantly, the synthesis does not need to be carried out on a linker designed for traceless synthesis; most of the synthetic approaches described herein were developed using standard, commercially available linkers (originally devised for solid-phase peptide synthesis). The type of structure prepared in a traceless fashion is not restricted. The individual synthetic approaches are divided into eight sections, each devoted to a different methodology for traceless synthesis. Each section consists of a brief outline of the synthetic strategy followed by a description of individual reported syntheses.

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“…Nanocrystalline metal oxides are gaining importance as catalysts for various organic transformations [119]. The protocol makes clever use of simultaneous cleavage of the support, and the prepared compounds 164 (Scheme 35) were found to be relevant in the design and synthesis of biologically important antiobesity and antimalarial drugs [122]. Model experiments using bulk Al 2 O 3 and basic alumina as catalysts proved to be less effective.…”

Section: Use Of Heterogeneous Catalysismentioning

confidence: 99%

Green Synthetic Approaches for Medium Ring-Sized Heterocycles of Biological Interest

Chattopadhyay¹

2015

Green Synthetic Approaches for Biologically Relevant Heterocycles

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Traceless solid-phase synthesis of multiple sulfonamide-containing cyclic sulfides exploiting microwave irradiation

Cited by 10 publications

References 16 publications

Iodine‐Catalyzed Oxidative Amination of Sodium Sulfinates: A Convenient Approach to the Synthesis of Sulfonamides under Mild Conditions

Iodine‐Catalyzed Oxidative Amination of Sodium Sulfinates: A Convenient Approach to the Synthesis of Sulfonamides under Mild Conditions

Traceless Solid-Phase Organic Synthesis

Green Synthetic Approaches for Medium Ring-Sized Heterocycles of Biological Interest

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