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Accelerated synthesis of phthalimide derivatives: Intrinsic reactivity of diamines towards phthalic anhydride evaluated by paper spray ionization mass spectrometry.
de Paula, Camila Cristina Almeida; Binatti, Ildefonso; Coelho Pimenta, João Victor; Augusti, Rodinei.
Afiliação
  • de Paula CCA; Departamento de Química, Universidade Federal de Minas Gerais, Belo Horizonte, Minas Gerais, Brazil.
  • Binatti I; Centro Federal de Educação Tecnológica, Belo Horizonte, Brazil.
  • Coelho Pimenta JV; Departamento de Química, Universidade Federal de Minas Gerais, Belo Horizonte, Minas Gerais, Brazil.
  • Augusti R; Departamento de Química, Universidade Federal de Minas Gerais, Belo Horizonte, Minas Gerais, Brazil.
Rapid Commun Mass Spectrom ; 36(24): e9407, 2022 Dec 30.
Article em En | MEDLINE | ID: mdl-36169595
RATIONALE: Paper spray (PS) is a simple and innovative ambient ionization technique for mass spectrometry (MS) analysis. Under PS-MS conditions, chemical reactions, which usually occur slowly on a bulk scale, are accelerated. Moreover, the formation of products and transient species can be easily monitored. In this manuscript, reactions between phthalic anhydride and diamines were conducted and monitored using a PS-MS platform. The reaction products (phthalimides) have many pharmaceutical applications, but their traditional syntheses can take hours under reflux, requiring laborious purification steps. METHODS: In situ reactions were performed by dropping methanolic solutions of phthalic anhydride and diamines on a triangular paper. The analyses were achieved by positioning the triangle tip in front of the mass spectrometer entrance, whereas a metal clip was attached to the triangle base. After adding methanol to the paper, a high voltage was applied across the metal clip, and the mass spectra were acquired. RESULTS: The intrinsic reactivity of alkyl and aromatic diamines was evaluated. The carbon chain remarkably influenced the reactivity of aliphatic diamines. For aryl diamines, the ortho isomer was the most reactive. Moreover, for aryl amines with electron-withdrawing substituents, no reaction was noticed. CONCLUSIONS: Taking advantage of the unique characteristics of PS-MS, it was possible to investigate the intrinsic reactivity of model alkyl (ethylene versus propylene) and aryl (o-phenylene versus m-phenylene and p-phenylene) diamines towards phthalic anhydride. Some crucial parameters that affect the intrinsic reactivity of organic molecules, such as isomerism, intramolecular interaction, and conformation, were easily explored.
Assuntos

Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Anidridos Ftálicos / Diaminas Tipo de estudo: Prognostic_studies Idioma: En Revista: Rapid Commun Mass Spectrom Ano de publicação: 2022 Tipo de documento: Article País de afiliação: Brasil País de publicação: Reino Unido

Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Anidridos Ftálicos / Diaminas Tipo de estudo: Prognostic_studies Idioma: En Revista: Rapid Commun Mass Spectrom Ano de publicação: 2022 Tipo de documento: Article País de afiliação: Brasil País de publicação: Reino Unido