A Facile Route to Substituted Dimethoxy Phosphonothionates Using Dimethyl Thiophosphite |
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| Authors: | Jeffrey Trautmann Alirica I. Suarez Pakamas Tongcharoensirikul Gregory W. Muth Charles M. Thompson |
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| Affiliation: | 1. Department of Pharmaceutical Sciences, School of Pharmacy , The University of Montana , Missoula , Montana , 59812-1512 , USA;2. Facultad de Farmacia , Universidad Central de Venezuela , APDO 40109, Caracas , 1041 , Venezuela |
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| Abstract: | Dimethyl thiophosphite reacts with aliphatic aldehydes and ketones, Michael acceptors, and N-benzyl imines to afford excellent yields of f -hydroxy phosphonothionates, g -substituted phosphonothionates and f -amino phosphonothionates, respectively. Dealkylation of f -amino phosphonothionates affords N-benzyl f -amino phosphonothioic acids. Dimethyl thiophosphite reacts with electrophiles at a significantly greater rate than dimethyl phosphite. |
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| Keywords: | α-Amino Phosphonothionates α-amino Phosphonothioic Acids α-hydroxy Phosphonothionates β-substituted Phosphonothionates Dimethyl Thiophosphite |
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