The formation of dimethyl amino(pyrene-1-yl)methylphosphonates in the Kabachnik-Fields reaction with dibenzyl phosphite, pyrene-1-carboxaldehyde and a non-aromatic amine in methanol

GRAPHICAL ABSTRACT

ABSTRACT

The Kabachnik-Fields reaction of pyrene-1-carboxaldehyde with dibenzyl phosphite and aliphatic amines in methanol led to the formation of dimethyl amino(pyren-1-yl)methyl-phosphonates, in some cases accompanied by dimethyl hydroxy(pyren-1-yl)methyl-phosphonate. These results are exclusive for the above compounds, in all other studied cases (aromatic aldehydes, aromatic amines) the mixtures of several aminophosphonates were obtained.

KEYWORDS:

• Transesterification
• pyrene-1-carboxaldehyde
• Kabachnik-Fields reaction
• dibenzyl phosphite

Funding

We thank the Polish National Centre of Science (NCN) for funding part of the work in the framework of the grant no. 2014/13/B/NZ9/02418.