Bronsted acidic ionic liquids: Green, efficient and reusable catalyst for synthesis of fluorinated Spiro [indole-thiazinones/thiazolidinones] as antihistamic agents

Bronsted acidic ionic liquid containing nitrogen-based organic cations 1-methylimidazolium and 1-butyl-3-methylimidazolium and inorganic anions such as BF4-, PF6- and PTSA(-) used as catalysts and reaction medium for synthesis of fluorinated spiro[3H-indole-3,2'-tetrahydro-1,3-thiazinel-2,4'(1H)- diones (4a-f), fluorinated spiro[3H-indole-3,2'-thiazolidine]-2,4' (1H)-diones (5a-f) in 90-97% yield by one-pot environmentally benign microwave induced technique. Synthesized compounds have been evaluated for their ability to inhibit the contractions induced by histamine on guinea pig ileum. The measurement of pA(2) values suggested that the reported compounds showed H1-antagonism. (c) 2012 Elsevier B.V. All rights reserved.