Amphoteric 2-(sulfonylamino)benzaldehydes, secondary amines and isocyanides in the multicomponent synthesis of elusive  N -alkyl-2,3-diaminoindoles

Giustiniano, Mariateresa; Pelliccia, Sveva; Sangaletti, Luca; Meneghetti, Fiorella; Amato, Jussara; Novellino, Ettore; Tron, Gian Cesare

doi:10.1016/j.tetlet.2017.09.076

Cited by 14 publications

(16 citation statements)

References 29 publications

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“…After the optimisation of the reaction conditions, we next explored the reaction scope. With this aim, we synthesized nine different 2-(sulfonylamino)benzaldehydes 7 and selected five commercially available isocyanides, and their random combination gave derivatives 14-31, as shown in Figure 3. When tertiary isocyanides were used, both electron-withdrawing and electron-donating groups were tolerated on the aromatic ring of 2-(sulfonylamino)benzaldehydes (15-19, 23-25, and 28-31), as well as a phenyl ring (26 and 27), while when primary and secondary isocyanides were employed, the corresponding products, albeit formed during the reaction, were not stable and were degraded during chromatographic purification.…”

Section: Resultsmentioning

confidence: 99%

“…Domino processes involving sequential chemical transformations are straightforward synthetic approaches to both drug-like heterocycles and molecular synthons being one-pot, atom economical and convergent reactions 6 . Recently, we reported the use of 2-(sulfonylamino)benzaldehydes as an amphoteric scaffold for the synthesis of functionalized N-alkyl-2,3-diaminoindoles 7 . The This journal is © The Royal Society of Chemistry 20xx…”

Section: Introductionmentioning

confidence: 99%

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On-water pyrrolidine-mediated domino synthesis of 2-iminoisatins

et al. 2018

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

On-water pyrrolidine-mediated domino synthesis of 2-iminoisatins

et al. 2018

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“…Synthesis of N ‐[2‐(Hydroxymethyl)phenyl]‐4‐methylbenzenesulfonamide (8): To a solution of N ‐(2‐formylphenyl)‐4‐methylbenzenesulfonamide 7 (57.5 mg, 0.21 mmol) in DMSO (2 mL), was added HCOONa · 2H 2 O (26.1 mg, 0.25 mmol), and the resultant mixture was stirred at 120 °C for 24 h. Then, the mixture was cooled to the room temperature, and water (5 mL) was added. The obtained mixture was extracted with CH 2 Cl 2 (5 mL × 2) and dried with Na 2 SO 4 .…”

Section: Methodsmentioning

confidence: 99%

Catalyst‐ and Additive‐Free Chemoselective Transfer Hydrogenation of α‐Keto Amides to α‐Hydroxy Amides by Sodium Formate

Hao

Liu

et al. 2019

Eur J Org Chem

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A catalyst‐ and additive‐free chemoselective transfer hydrogenation of α‐keto amides to α‐hydroxy amides is easily achieved by using sodium formate as a hydrogen source. The utility of this method is demonstrated by gram‐scale synthesis and transformation of the resultant α‐hydroxy amides into polysubstituted acetamides and 2‐arylindole derivatives. Control experiments suggest that the NH group of α‐keto amides is crucial for the chemoselective reduction through the formation of hydrogen bonds.

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“…The success of this novel multicomponent transformation lies in presence of the amphoteric sulfonylamino group, which sequentially acts as a Brønsted acid and as a nucleophile, without the need for additional catalysts. 71…”

Section: Review Syn Thesismentioning

confidence: 99%

Interrupted Ugi and Passerini Reactions: An Underexplored Treasure Island

et al. 2018

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The formation of the key short-lived intermediate nitrilium ion in the Passerini and Ugi reactions was recognized early in the discovery of these two-multicomponent transformations. Surprisingly, the idea of intramolecularly intercepting it, eluding the attack by the carboxylate, and thus interrupting the normal course of the reaction, was missed by chemists for several decades. In this review we describe, in an exhaustive manner, the reported synthetic approaches, which can be categorized as interrupted Passerini/Ugi reactions. Besides, the clear goal of this review is to show the potential of these transformations, whilst highlighting the underexplored combinations of reagents toward the identification of novel interrupted Passerini/Ugi reactions.1 Introduction2 The Interrupted Ugi Reaction2.1 The Interrupting Functional Group is Present on the Amine Reactant2.2 The Interrupting Functional Group is Present on the Isocyanide Reactant2.3 The Interrupting Functional Group is Present on the Carbonyl Reactant3 The Interrupted Passerini Reaction3.1 The Interrupting Functional Group is Present on the Carbonyl Reactant3.2 The Interrupting Functional Group is Present on the Isocyanide Reactant4 Conclusions and Future Outlook

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Amphoteric 2-(sulfonylamino)benzaldehydes, secondary amines and isocyanides in the multicomponent synthesis of elusive N -alkyl-2,3-diaminoindoles

Cited by 14 publications

References 29 publications

On-water pyrrolidine-mediated domino synthesis of 2-iminoisatins

On-water pyrrolidine-mediated domino synthesis of 2-iminoisatins

Catalyst‐ and Additive‐Free Chemoselective Transfer Hydrogenation of α‐Keto Amides to α‐Hydroxy Amides by Sodium Formate

Interrupted Ugi and Passerini Reactions: An Underexplored Treasure Island

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