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

Paulo F. M. Oliveira (1) , Naoki Haruta (2) , Alain Chamayou (1) , Brigitte Guidetti (3) , Michel Baltas (3) , Kazuyoshi Tanaka (2) , Tohru Sato (2, 4) , Michel Baron (1)

1 RAPSODEE - Centre de recherche d'Albi en génie des procédés des solides divisés, de l'énergie et de l'environnement
2 Graduate School of Engineering, Kyoto University
3 SPCMIB - Synthèse et Physico-Chimie de Molécules d'Intérêt Biologique
4 Unit of Element Strategy Initiative for Catalysts & Batteries, ESICB, Kyoto University

Compared mechanosynthesis of two condensed 1,4-diazines were investigated in ball milling conditions from o-phenylenediamine. C-13 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 9,10-phenanthrenequinone.

Mots clés: Diazines; Mechanochemistry; Ball milling; Reaction mechanism; Reaction intermediates

Domaines: Sciences de l'ingénieur [physics]

Paulo F. M. Oliveira, Naoki Haruta, Alain Chamayou, Brigitte Guidetti, Michel Baltas, et al.. Comprehensive experimental investigation of mechanically induced 1,4-diazines synthesis in solid state. Tetrahedron, 2017, 73 (16), p.2305-2310. ⟨10.1016/j.tet.2017.03.014⟩. ⟨hal-01619243⟩