2-Substituted perimidines: Zwitterionic tauterism in solid state, substituent effect on their crystal packing and biological activity

Fernández‐Gijón, César Augusto; Olvera‐Mancilla, Jessica; Lagadec, Ronan Le; Barba-Behrens, Noráh; Rico-Bautista, Hugo; Toscano, Rubén A.; Alexandrova, Larissa

doi:10.1016/j.molstruc.2021.132056

Cited by 3 publications

(1 citation statement)

References 52 publications

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“…Nitrogen-containing tricyclic heterocycles, [26] such as perimidines and 2,3-dihydro-1H-perimidines, are omnipresent in various natural products [27] and exhibit several biological activities, [28] photochromic properties [29] and other peculiar features commonly used in different fields. [30] Concerning the synthesis of these N-heterocycle scaffolds, several traditional methods were well documented in the literature, [31] but longer reaction times, high temperatures, use of hazardous solvents, expensive reagents, and lower yield of the products are the major drawbacks.…”

Section: Benzimidazolesmentioning

confidence: 99%

Application of Bertagnini's Salts in a Mechanochemical Approach Toward Aza‐Heterocycles and Reductive Aminations via Imine Formation

Behera,

Kanti Bera,

Basoccu

et al. 2024

Adv Synth Catal

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Our research has demonstrated that mechanochemical activation is more effective with solid reagents. We have showcased the practicality of Bertagnini's salts, also called aldehyde‐bisulfite adducts, which are crystalline, simplifying preparation and storage. These salts are stable substitutes for liquid aldehydes and ketones that have been effectively employed in reductive amination, synthesizing aza‐heterocycles and hydrazones within mechanochemistry. The technique's effectiveness broadens the substrate scopes, simplifies purification, reduces reaction times, and delivers good product yields. Additionally, the thermal stability of the bisulfite adducts has been confirmed through TGA (Thermogravimetric analysis) analysis.

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