Sodium Cyanate Mediated Synthesis of Sulfonylurea and Sulfonyltriuret from Sulfonyl Chloride and Amine. Issue 10 (5th July 2016)

• Record Type: Journal Article
• Authors: Hadianawala, Murtuza; Shaik, Althaf; Hasija, Nisha; Vasu, Anuji K.; Datta, Dr Bhaskar
• Is Part Of: ChemistrySelect. Volume 1:Issue 10(2016)
• Page Start: 2212
• Page End: 2216
• Publication Date: 2016-07-05
• Subjects: Sulfonylurea -- Sulfonyltriuret -- Sulfonyl chloride -- Hypoglycemic drugs -- Herbicides; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/slct.201600259
• Languages: English
• ISSNs: 2365-6549

Abstract

Abstract: Synthetic methods providing access to sulfonylureas are immensely valuable considering the wide usage of sulfonylurea derivatives as hypoglycemic drugs and herbicides. In this work, the scope of a sodium cyanate mediated single‐step synthesis of sulfonylureas from amines and sulfonyl chlorides as starting materials has been examined. Success of the single‐step reaction in affording desired aliphatic and aromatic sulfonylurea products depends on the combination of suitable nucleophilicity of amines and reactivity of sulfonyl chlorides. In addition to providing access to sulfonylureas, the interplay of reactivities of the amine and sulfonyl chloride is found to result in emergence of specific oligomeric products that are characterized as novel sulfonyltriurets. In effect, the sodium cyanate mediated single‐step reaction for synthesis of sulfonylureas also provides a method for synthesis of specific sulfonyltriurets. Electronic effects accompanying the amine and sulfonyl chloride modulate the nature of major product between sulfonylureas and sulfonyltriurets. The sodium cyanate mediated single‐step reaction is thus sought to be considered as a method for synthesis of sulfonyltriurets in addition to sulfonylureas. Abstract : A single‐step method for synthesis of sulfonylureas and sulfonyltriurets from amine and sulfonyl chloride starting materials is described. The sodium cyanate mediated reaction permits synthesis of aliphatic and aromatic sulfonylureas. The reaction also affords facile access to novel sulfonyltriurets. Electronic effects surrounding the amine and sulfonyl chloride starting materials control the proportion of sulfonylurea and sulfonyltriuret products.