�ber N1-Alkylsulfonyl-N2-butylharnstoffe

Pantlitschko, M; Salvenmoser, F.

doi:10.1007/bf00898783

Cited by 5 publications

(2 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…We attempted the conversion of amines into corresponding urea derivatives followed by treatment with sulfonyl chlorides, but were unable to obtain the sulfonylurea derivatives. Our exploration was further necessitated by very few reports describing the synthesis of aliphatic sulfonylureas . We were drawn to the earlier methods of synthesis that used sulfonyl chlorides instead of sulfonamide as a starting material .…”

Section: Introductionmentioning

confidence: 99%

Sodium Cyanate Mediated Synthesis of Sulfonylurea and Sulfonyltriuret from Sulfonyl Chloride and Amine

et al. 2016

View full text Add to dashboard Cite

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.

show abstract

Section: Introductionmentioning

confidence: 99%

Sodium Cyanate Mediated Synthesis of Sulfonylurea and Sulfonyltriuret from Sulfonyl Chloride and Amine

et al. 2016

View full text Add to dashboard Cite

show abstract

“…Synthesis of sulfonylureas with aliphatic sidechains is challenging owing to the limited literature on the subject. 15,16 Our attempts to use common methods for the synthesis of sulfonylureas, namely treatment of sulfonamide with isocyanate in presence of base or conversion of sulfonamide into their carbamate derivatives followed by treatment with amines, did not yield desired aliphatic sulfonylureas. The synthesis of sulfonylurea by treatment of sulfonyl chloride with amine in presence of cyanate has been reported previously.…”

mentioning

confidence: 99%