Regiospecific synthesis of N,N’-disubstituted-2-imino-hydantoins derived from cyanamides

Abstract

The present work developed a new simple method and convenient procedure to synthesize a novel series of 1-(4,6-dimethylpyrimidin-2-yl)-2-imino-3-arylimidazolidin-4-ones 3. The sodium salt of N-(4,6-dimethylpyrimidin-2-yl)cyanamide (1) was selected to use as the starting material to undergo intramolecular cyclization reaction with 2-chloro-N-arylacetamides in boiling acetone for about 12–18 hours. According to this new synthetic route, eleven imino-hydantoins were readily separated in moderate to excellent yields as single products after cooling the reaction without any purification technique. Also, on the basis of the experimental results and analysis data (IR, NMR, elemental analyses, and GC-MS spectra), the reaction is regiospecific as well as a plausible mechanism to form the target products 3 instead of di-imino-oxazolidines 4 and/or 2-imino-2,3-dihydro-oxazoles 5 is proposed.

HIGHLIGHTS

• A successful synthesis of novel series of N,N’-disubstituted-2-iminohydantoins.

• There are regiospecifity for the formation of 2-iminohydantoins instead of di-imino-oxazolidines and/or 2-imino-2,3-dihydro-oxazoles.

• The structures of title compounds were established by using IR, NMR, elemental analyses and GC-MS spectral data.

Graphical Abstract

Keywords:

• Cyanamide
• iminohydantoin
• regiospecific
• imidazolidin-4-one
• intramolecular cyclization

Declaration of interest

The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.

Additional information

Funding

This work was supported by the Deanship of Scientific Research, Vice Presidency for Graduate Studies and Scientific Research, King Faisal University, Saudi Arabia [Grant No. KFU241157].