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Intramolecular catalysis of aminolysis of phosphorus heterocycles incorporating an α‐aminoamide moiety. III. Synthesis of 2‐oxo or 2‐thioxo 1,3‐disulfonyl‐1,3,2‐diazaphospholidines and reactions with amines and alcohols
Author(s) -
Dujols Frédéric J. M.,
Mulliez Michel E.
Publication year - 2001
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570380227
Subject(s) - aminolysis , chemistry , steric effects , moiety , intramolecular force , pyridine , hydrolysis , catalysis , organic chemistry , condensation , medicinal chemistry , physics , thermodynamics
A series of 2‐oxo or 2‐thioxo 1,3‐disulfonyl‐1,3,2‐diazaphospholidines 4 was prepared by condensation of phosphonyl dichlorides 2 with bis‐ N,N' ‐sulfonylethylenediamines 1 in pyridine. Complete aminolysis or alcoholysis of heterocycles 4 took place with regeneration of sulfonyldiamines 1 . These reactions are very sensitive to steric hindrance, and hydrolysis is generally favoured over aminolysis. The results are discussed in terms of mechanisms of phosphorylation.