Comprehensive experimental investigation of mechanically induced 1,4-diazines synthesis in solid state

Abstract

Compared mechanosynthesis of two condensed 1,4-diazines were investigated in ball milling conditions from o-phenylenediamine. 13 C CP-MAS NMR revealed a hemiaminal intermediate for dibenzo[a,c] phenazine synthesis accumulated under mechanical action, as confirmed by calorimetry. Such intermediate, which is not detected in the case of 2,3-diphenylquinoxaline synthesis, provides experimental evidence of a concerted reaction between highly reactive mechanically-excited diamine and 9,10phenanthrenequinone.

Mechanochemical Synthesis and Biological Evaluation of Novel Isoniazid Derivatives with Potent Antitubercular Activity

“…It is still important to mention that, differently from the phenolic hydrazones, a melting was produced when the p -TSA was added, and, therefore, the reaction was not fully in solid-state. The formation of a fluid phase is vastly found for solid mixtures (eutectic melting) [ 68 ] and surely contributed to reach high conversions in short times of grinding for these hydrazones.…”

Investigating the role of reducing agents on mechanosynthesis of Au nanoparticles

“…45 Moreover, these dominant kinetic features are consistent with other mechanochemical transformations -e.g. cocrystal and salt formation, [55][56][57][58] and covalent bond-forming reactions [59][60][61][62] -suggesting the same physical effects guide the apparent macroscopic rate of Au NP BUMS. The magnitude of the induction period depends markedly on the choice of R A , following as HQ < AA < NaBH 4 < Ctr, Fig.…”

Tribochemistry, Mechanical Alloying, Mechanochemistry: What is in a Name?

“…To date, mechanochemical approaches being applied to transformations from across the chemical sciences have been reported, spanning from the synthesis of inorganic and organic compounds [including those as complex as peptides ( Hernández et al, 2017 ; Maurin et al, 2017 )] through to the preparation of large porous frameworks such as metal-organic frameworks [MOFs( Stolar et al, 2017 ; Stolar and Užarević, 2020 ; Wang et al, 2020 ; Zhou et al, 2020 ; Głowniak et al, 2021 ; Stolar et al, 2021 )]. Moreover, the scale of mechanochemical reactions has ranged from the mechanical manipulation of single atoms and molecules (predominantly, synthetic and natural polymers) using atomic force microscopy ( Kaupp, 2009 ; Ribas-Arino and Marx, 2012 ; Makarov, 2016 ; Li et al, 2017 ) to the induction of reactions in multi-component inorganic and organic powder mixtures in ball milling reactors or extruders ( Iwasaki et al, 2010 ; Am Ende et al, 2014 ; Oliveira et al, 2017 ; Andersen and Mack, 2018b ; Egleston et al, 2020 ). Alongside synthetic covalent chemical reactions, a wide range of supramolecular assemblies have been also prepared by mechanical treatment, including cocrystals and salts ( Myz et al, 2009 ; Weyna et al, 2009 ; Friščić, 2012 ; Myz et al, 2012 ; Braga et al, 2013 ; Hasa et al, 2015 ), as well as non-covalently bound mechano-composites such as drug delivery devices comprising active pharmaceutical ingredients with excipients ( Shakhtshneider et al, 2007 ; Shakhtshneider et al, 2014a ; Shakhtshneider et al, 2014b ; Lomovsky et al, 2017 ; Ogienko et al, 2018 ; Bychkov et al, 2019 ; Adekenov et al, 2020 ; Skripkina et al, 2020 ).…”

“…Moreover, the scale of mechano-chemical reactions has ranged from the mechanical manipulation of single atoms and molecules (predominantly, synthetic and natural polymers) using atomic force microscopy [52][53][54][55] to the induction of reactions in multi-component powder mixtures in ball milling reactors or extruders. [56][57][58][59][60] Alongside synthetic covalent chemical reactions, a wide range of supramolecular assemblies have been also prepared by mechanical treatment, including cocrystals and salts, [61][62][63][64][65][66] as well as non-covalently bound mechano-composites such as drug delivery devices comprising active pharmaceutical ingredients with excipients. [67][68][69][70][71][72][73] Moreover, many mechanochemical processes have been successfully scaled-up, 49,56,58,[74][75][76][77][78][79][80] offering a direct route to translate mechanochemistry from laboratory curiosity to industrial applications.…”