Recent synthetic applications of α-amido sulfones as precursors of <i>N</i>-acylimino derivatives

Marcantoni, Enrico; Palmieri, Alessandro; Petrini, Marino

doi:10.1039/c9qo00196d

Cited by 45 publications

(35 citation statements)

References 268 publications

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“…The latter, however, has only been superficially explored, again mainly using carbamates, although some individual examples with benzamides are present. 13 , 14 , 18 − 21 Also, in the corresponding paper by Petrini, only aromatic aldehydes were found to be reliable reaction partners. 13 Yields decreased with aliphatic aldehydes and these substrates were not further explored.…”

Section: Introductionmentioning

confidence: 91%

“… 13 , 14 , 18 − 21 Also, in the corresponding paper by Petrini, only aromatic aldehydes were found to be reliable reaction partners. 13 Yields decreased with aliphatic aldehydes and these substrates were not further explored. An alternative but comparable strategy was reported by Katritzki and co-workers, who stabilized the N -acylimine intermediate with benzotriazole.…”

Section: Introductionmentioning

confidence: 91%

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Strecker-Derived Methodology for Library Synthesis of N-Acylated α-Aminonitriles

et al. 2021

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The Strecker reaction is a three-component condensation of an aldehyde, an amine, and hydrogen cyanide, delivering an α-amino carbonitrile. Despite extensive investigations, the possibility to use amides instead of amines as one of the three condensation partners has been largely neglected. Nonetheless, the N-acylated α-aminocarbonitriles that are obtained in this way are of direct interest for drug discovery, because they make up a well-known class of mechanism-based inhibitors of serine-and cysteinetype hydrolases. In response, we have thoroughly explored the corresponding variant of the Strecker reaction, focusing on catalyst use, solvent, reaction time, and cyanide source. Optimized parameters were combined in a sequential one-pot protocol for which the scope was found to be compatible with library synthesis applications. Product yields ranged from 7 to 90%, and conditions were found to be mild and tolerant to a wide range of functional groups, including moieties that are typically present in druglike molecules.

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Section: Introductionmentioning

confidence: 91%

Section: Introductionmentioning

confidence: 91%

Strecker-Derived Methodology for Library Synthesis of N-Acylated α-Aminonitriles

et al. 2021

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“…Considering that Lewis acids are known to promote the elimination of arylsulfinyl group from sulfonyl indoles, a direct assistance of magnesium salts in the generation of the alkylideneindolenine intemediate V could be envisaged. [21] The optimized reaction conditions have been applied to a series of sulfonyl indoles 1 and indoles 2 leading to the results displayed in Table 2. Sulfonyl indoles 1 bearing aliphatic or aromatic side chains usually give satisfactory results with a wide range of indolylmagnesium bromide reagents 2.…”

Section: Full Papermentioning

confidence: 99%

Synthesis of Unsymmetrical Bisindolylmethanes by Reaction of Indolylmagnesium Bromides with Sulfonyl Indoles

2020

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Sulfonyl indoles are widely recognized as alkylideneindolenine precursors amenable to provide functionalized indole derivatives upon reaction with nucleophiles. In this paper reaction of sulfonyl indoles with indolylmagnesium bromides is used to access unsymmetrical bisindolylmethanes. The target compounds are obtained in satisfactory yields starting from a wide range of substrate/reagent combinations. The utilization of pyrrolylmagnesium bromides for the same reaction also affords the expected adducts albeit in moderate yield.

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“…Compounds obtained from these reactions accompanied by Schiff bases have been used in the treatment of various diseases due to their biological activity [23]. Many reagents have been used for the synthesis of imines such as Lewis acids [24][25][26][27], metal complex [28,29], metal-free conditions [30,31], promoted by microwave irradiation [32] and ultrasound radiation [33].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of New Schiff Base Compounds and Identification of Their Structures

Berber¹

2020

Adıyaman University Journal of Science

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Schiff bases (imines) have been frequently used in various fields such as medicine, pharmaceutical purposes due to their various biological properties. In this study, nine new imine compounds (3a-h) were synthesized from 1-naphthyl amine with aromatic aldehydes in MeOH and their chemical structures were defined by 1H/13C NMR, IR and elemental analysis studies. We observed a singlet one hydrogen of the imines (-CH=N-) at 8.56-8.86 ppm in the 1H NMR spectra and also carbon of the Schiff bases (-CH=N-) at 158.2-163.4 ppm in the 13C NMR spectra. Also the IR spectra displayed the (-C=N-) characteristic absorption band at around 1600 cm-1. The obtained characteristic peaks at the expected locations proved the structural accuracy of the synthesized new derivative Schiff bases.

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Recent synthetic applications of α-amido sulfones as precursors of N-acylimino derivatives

Cited by 45 publications

References 268 publications

Strecker-Derived Methodology for Library Synthesis of N-Acylated α-Aminonitriles

Strecker-Derived Methodology for Library Synthesis of N-Acylated α-Aminonitriles

Synthesis of Unsymmetrical Bisindolylmethanes by Reaction of Indolylmagnesium Bromides with Sulfonyl Indoles

Synthesis of New Schiff Base Compounds and Identification of Their Structures

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