新型螺[色烯并(2,3-c)吡唑-4,1’-异苯并呋喃]-3’-酮类化合物的合成及光学性能研究

Synthesis and Optical Properties of Novel Spiro[chromo(2,3-c)-pyrazole-4,1’-isobenzofuran]-3’-one Compounds

在酸催化及脱水作用下,以2-(4-二丁基氨基-2-羟基苯甲酰基)苯甲酸或2-(4-二乙基氨基-2-羟基苯甲酰基)苯甲酸和吡唑啉酮为原料,通过Knoevenagel缩合和脱水反应,合成了一系列新型螺[色烯并(2,3-c)吡唑-4,1’-异苯并呋喃]-3’-酮类化合物.考察了反应物配比、催化剂、温度和时间等因素对反应的影响,初步探究了所合成化合物在不同pH、溶剂中的光学性能,其中1-(4-氯苯基)-7-(二乙基氨基)-3-甲基-1H,3’H-螺[色烯并[2,3-c]吡唑-4,1’-异苯并呋喃]-3’-酮(1e)和1-(4-氯苯基)-7-(二丁基氨基)-3-甲基-1H,3’H-螺[色烯并[2,3-c]吡唑-4,1’-异苯并呋喃]-3’-酮(1j)有潜力作为强酸强碱的pH指示剂.

A series of novel spiro[chromo(2,3-c)pyrazole-4,1’-isobenzofuran]-3’-one compounds were synthesized via Knoevenagel condensation and dehydration reaction of 2-(4-dibutylamino-2-hydroxybenzoyl)benzoic acid or 2-[4-(diethylamino)-2-hydroxybenzoyl]benzoic acid with pyrazolones using acid as catalysts and dehydrants. The effects of the ratio of the substrates, catalyst, temperature and reaction time were examined. Their optical properties in different pH and solvent were investigated. It shows that 1-(4-chlorophenyl)-7-(diethylamino)-3-methyl-1 H,3’H-spiro[chromene[2,3-c]pyrazole-4,1’-isobenzofuran]-3’-one(1 e) and 1-(4-chlorophenyl)-7-(dibutylamino)-3-methyl-1 H,3’H-spiro[chromene[2,3-c]pyrazole-4,1’-isobenzofuran]-3’-one(1 j) have potential as pH indicators for strong acids and bases.