123269-09-0Relevant articles and documents
A New Route to N-Monosubstituted Thioamides Utilizing Phosphoramidothionates as Reagents for the Thioamidation of Carboxylic Acids
DeBruin, Kenneth E.,Boros, Eric E.
, p. 6091 - 6098 (2007/10/02)
Several N-monosubstituted thioamides have been synthesized from the corresponding carboxylic acid chlorides and primary amines by a new procedure.The procedure utilizes a commercially available and inexpensive organophosphorus reagent (dimethyl chlorothiophosphate) to derivatize the amine, form the carboxamide bond, and accomplish the thionation of the carbonyl by an intramolecular rearrangement.The phosphoryl group is then cleaved from the resulting thiocarbonyl phosphoryl mixed imide by a simple hydrolysis.Thioamides (RCSNHR') containing a variety of functionality(R= simple alkyl, phenyl, bulky alkyl, cycloalkylalkyl, α,β-unsaturated, and alkyl with remote keto, ester, or amide carbonyl groups; R'= methyl, benzyl, allyl) have been prepared by this method in generally high overall yields (50-80 percent).Competing thionation of remote carbonyl groups or epimerization of a chiral center containing a proton α to a ketone group was not observed.
A NEW ROUTE TO PHOSPHORYL THIOCARBONYL MIXED IMIDES - STRUCTURE LIMITATIONS
De Bruin, Kenneth E.,Boros, Eric E.
, p. 139 - 142 (2007/10/02)
The rearrangement of N-methyl thiophosphoryl carbonyl mixed imides (I, XYP(S)N(Me)C(O)Z) to N-methyl phosphoryl thiocarbonyl mixed imides (II, XYP(O)N(Me)C(S)Z) was studied as a function of substitution on phosphorus (Ia: X = Y = MeO; Ib: X = Ph, Y = MeO;
AN UNUSUAL REARRANGEMENT OF N-SUBSTITUTED THIOPHOSPHORYL CARBONYL MIXED IMIDES
DeBruin, Kenneth E.,Boros, Eric E.
, p. 1047 - 1050 (2007/10/02)
N-Substituted O,O-dimethyl N-benzoyl phosphoramidothioates (III, R=Me, Ph but not H) undergo an uncatalyzed unimolecular rearrangement in an inert solvent; whereby, the carbonyl oxygen atom exchanges position with the thiophosphoryl sulfur atom (an O,S Sw
