Alkylation of N-arylcyanamides and electron-deficient phenols with (chloromethyl)thiirane

作者：Butkevich A N; Zibinsky M; Sokolov V V^*; Tomashevskii A A

来源：Chemistry of Heterocyclic Compounds, 2012, 47(12): 1509-1515.

DOI：10.1007/s10593-012-0941-2

• 3-aminothietanes
• N-arylcyanamides
• (chloromethyl)thiirane
• phenols
• thiirane-thietane rearrangement

Alkylation of N-arylcyanamides with (chloromethyl)thiirane in aqueous alkaline solution provides an easy synthetic approach to N-aryl-N-(thietan-3-yl)cyanamides. Yields vary from 34 to 76% and are lower in the case of electron-deficient aryl substituents. The reaction with phenols containing electron-withdrawing groups results in formation of 3-(aryloxy)thietanes in 19-45% yields.

• 出版日期2012-3