Formation of Thioureas by Reaction of Isothiocyanates with Weakly Basic or Betaine Amines Promoted by DMAP
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| Year of publication | 2007 |
| MU Faculty or unit | |
| Citation | |
| Description | Several thousand papers and patents refer since 1970s that activation of acyl, alkoxycarbonyl or aryloxycarbonyl synthons for their coupling with N, O, C nucleophiles may be very effectively realized by an addition of 4 N,N dialkylaminopyridine (DMAP) in catalytic amount [1]. On the other hand, formation of thioureas is not easy for reactions starting from small reactive isothiocyanates (e. g. alkyl, electron donor substituted aryl or heteroaryl isothiocyanates) and/or weakly basic or betaine amines (amino acids). The last mentioned betaines are insoluble in non polar organic solvents and reactions must be frequently carried out for the most part in heterogenous two phase systems or in water organic solvents mixture very often with poor yields. The activation of organic isothiocyanates for reactions with small reactive isothiocyanates and/or weakly basic or betaine amines by DMAP will be demonstrated. |
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