I. N. Bardasov, R. Golubev, O. V. Ershov
Sep 14, 2011
Citations
0
Influential Citations
11
Citations
Journal
Tetrahedron Letters
Abstract
The one-pot reactions of 2-[amino(2-cyano-3-aryloxiran-2-yl)methylene]malononitriles with thiocyanate to afford 5-amino-3-arylfuro[3,2-c]isothiazole-6-carbonitriles in good yields. 2011 Elsevier Ltd. All rights reserved. Cascade-heterocyclization reactions have a special place in modern organic synthesis and achieve complicated chemical transformations in one synthetic operation. Their use in reactions of cyano-containing compounds allows the synthesis of functional mono-, bi-, and polycyclic structures. 1 Prospective substrates for the synthesis of new heterocyclic compounds are 2-[amino(2-cyano-3-aryloxiran-2-yl)methylene]malononitriles 1, 2 which are obtained by epoxidation of arylmethylidene derivatives of malononitrile dimers. 3 The use of these compounds in organic synthesis has enabled the development of one-pot syntheses of 5-amino-3-arylfuro[3,2-c]isothiazole-6-carbonitriles 2. The presence of enaminecarbonitrile moieties makes them promising for further chemical transformations. Besides some isothiazole derivatives are known to possess cytotoxic, antiproliferative, antiviral, antibacterial, and antipsychotic activity. 4