ONE-POT SYNTHESIS OF ISOBENZOFURAN-1(3H)-ONES USING SULFURIC ACID IMMOBILIZED ON SILICA UNDER SOLVENT-FREE CONDITIONS AND SURVEY OF THIRD-ORDER NONLINEAR OPTICAL PROPERTIES

Abstract

ABSTRACT Solvent-free synthesis of isobenzofuran-1(3 H )-ones have been described via reaction of phthalaldehydic acid (2-carboxybenzaldehyde) with methylaryl or cyclic ketones using sulfuric acid immobilized on silica (H 2 SO 4 -SiO 2 ) in excellent yields (70–88%). The catalyst can be recovered by simple filtration and reused. Also, some of these compounds has been studied the third-order nonlinear optical properties by laser Gaussian z-scan techniques. e-mail: b.maleki@hsu.ac.ir INTRODUCTION Isobenzofuran-1(3 H )-ones and their derivatives are very important biological compounds that occur widely in natural products. Typical examples are are fuscinarin ( 1 ) 1 , typhaphthalide ( 2 ) 2 , catalpalactone ( 3 ) 3 , alcyopterosin E ( 4 ) 4 , (+)-spirolaxine ( 5 ) 5 , vermistatin ( 6 ) 6 , rubiginone-H ( 7 ) 7 , (-)-hydrastine ( 8 ) 8 , isopestacin ( 9 ) 9 , and cryphonectricacid ( 10 ) 10 . Figure 1. Some members of this family have displayed interesting physiological activities and found attractive applications in medicinal chemistry, being used as anti-bacterial, anti-convulsant, anti-HIV, anti-asthmatic, anti-tumor, anti-plateletactivities, anesthesiaprolongation, and PGF