Synthesis and arylation of unprotected sulfonimidamides

Maldonado, Matías F.; Sehgelmeble, Fernando W.; Bjarnemark, Fanny; Svensson, Mats; Åhman, Jens; Arvidsson, Per I.

doi:10.1016/j.tet.2012.06.072

Cited by 58 publications

(25 citation statements)

References 27 publications

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“…Organolithium reagent 11 was obtained from the corresponding bromide and employed in the synthesis of three sulfonimidamides (12)(13)(14). [22] Pleasingly,t he parent sulfonimidamide (17)c ould be prepared in high yield by oxidative cleavage of the DMBprotected sulfonimidamide 14. [22] Pleasingly,t he parent sulfonimidamide (17)c ould be prepared in high yield by oxidative cleavage of the DMBprotected sulfonimidamide 14.…”

Section: Angewandte Chemiementioning

confidence: 99%

One‐Pot, Three‐Component Sulfonimidamide Synthesis Exploiting the Sulfinylamine Reagent N‐Sulfinyltritylamine, TrNSO

2017

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Sulfonimidamides are increasingly important molecules in medicinal chemistry and agrochemistry, but their preparation requires lengthy synthetic sequences, which has likely limited their use. We describe a one-pot de novo synthesis of sulfonimidamides from widely available organometallic reagents and amines. This convenient and efficient process uses a stable sulfinylamine reagent, N-sulfinyltritylamine (TrNSO), available in one step on 10 gram scale, as a linchpin. In contrast to classical approaches starting from thiols or their derivatives, our TrNSO-based approach facilitates the rapid assembly of the three reaction components into a variety of differentially substituted sulfonimidamides containing medicinally relevant moieties, including pyridines and indoles. Analogues of the sulfonamide-containing COX-2 inhibitor Celecoxib were prepared and evaluated.

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Section: Angewandte Chemiementioning

confidence: 99%

One‐Pot, Three‐Component Sulfonimidamide Synthesis Exploiting the Sulfinylamine Reagent N‐Sulfinyltritylamine, TrNSO

2017

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“…Possibilities for further functionalization on these complex structures were explored; N-alkylation of 12 with methyl iodide proceeded quantitatively (15), while N-arylation via ap alladium-catalyzed cross-coupling was also successful (16). [22] Pleasingly,t he parent sulfonimidamide (17)c ould be prepared in high yield by oxidative cleavage of the DMBprotected sulfonimidamide 14.…”

Section: Angewandte Chemiementioning

confidence: 99%

One‐Pot, Three‐Component Sulfonimidamide Synthesis Exploiting the Sulfinylamine Reagent N‐Sulfinyltritylamine, TrNSO

2017

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Sulfonimidamides are increasingly important molecules in medicinal chemistry and agrochemistry,b ut their preparation requires lengthy synthetic sequences,w hich has likely limited their use.Wedescribe aone-pot de novo synthesis of sulfonimidamides from widely available organometallic reagents and amines.This convenient and efficient process uses astable sulfinylamine reagent, N-sulfinyltritylamine (TrNSO), available in one step on 10 gram scale,asalinchpin. In contrast to classical approaches starting from thiols or their derivatives, our TrNSO-based approach facilitates the rapid assembly of the three reaction components into av ariety of differentially substituted sulfonimidamides containing medicinally relevant moieties,i ncluding pyridines and indoles.A nalogues of the sulfonamide-containing COX-2 inhibitor Celecoxib were prepared and evaluated. Scheme 1. a) At ypical linear synthesis of sulfonimidamides via the intermediacy of unstable sulfinyl chlorides.b )This work:aone-pot sulfinylamine-based synthesis of sulfonimidamides.

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“…[51][52][53][54][55] Generally conditions for Bn group removal entail use of 10% Pd/C catalyst at >40 bar and >40°C, [52][53][54][56][57][58] with Cbz groups are amenable to removal at lower temperatures and pressures. [51][52][53][54][55] Generally conditions for Bn group removal entail use of 10% Pd/C catalyst at >40 bar and >40°C, [52][53][54][56][57][58] with Cbz groups are amenable to removal at lower temperatures and pressures.…”

Section: Hydrogenolysis Of Alcohols and Aminesmentioning

confidence: 99%

The expanding utility of continuous flow hydrogenation

et al. 2015

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There has been an increasing body of evidence that flow hydrogenation enhances reduction outcomes across a wide range of synthetic transformations. Moreover flow reactors enhance laboratory safety with pyrophoric catalysts contained in sealed cartridges and hydrogen generated in situ from water. This mini-review focuses on recent applications of flow chemistry to mediate nitro, imine, nitrile, amide, azide, and azo reductions. Methodologies to effect de-aromatisation, hydrodehalogenation, in addition to olefin, alkyne, carbonyl, and benzyl reductions are also examined. Further, protocols to effect chemoselective reductions and enantioselective reductions are highlighted. Together these applications demonstrate the numerous advantages of performing hydrogenation under flow conditions which include enhanced reaction throughput, yields, simplified workup, and the potential applicability to multistep and cascade synthetic protocols.

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Synthesis and arylation of unprotected sulfonimidamides

Cited by 58 publications

References 27 publications

One‐Pot, Three‐Component Sulfonimidamide Synthesis Exploiting the Sulfinylamine Reagent N‐Sulfinyltritylamine, TrNSO

One‐Pot, Three‐Component Sulfonimidamide Synthesis Exploiting the Sulfinylamine Reagent N‐Sulfinyltritylamine, TrNSO

One‐Pot, Three‐Component Sulfonimidamide Synthesis Exploiting the Sulfinylamine Reagent N‐Sulfinyltritylamine, TrNSO

The expanding utility of continuous flow hydrogenation

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