Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (2): 501-510.DOI: 10.6023/cjoc201907033 Previous Articles     Next Articles


岳永双, 解正峰, 褚义成, 薛松松   

  1. 西南石油大学化学化工学院 油气田应用化学四川省重点实验室 成都 615000
  • 收稿日期:2019-07-24 修回日期:2019-09-09 发布日期:2019-10-09
  • 通讯作者: 解正峰
  • 基金资助:

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

Yue Yongshuang, Xie Zhengfeng, Chu Yicheng, Xue Songsong   

  1. Oil&Gas Field Applied Chemistry Key Laboratory of Sichuan Province, College of Chemistry and Chemical Engineering, Southwest Petroleum University, Chengdu 610500
  • Received:2019-07-24 Revised:2019-09-09 Published:2019-10-09
  • Supported by:
    Project supported by the Youth Science and Technology Innovation Team of Southwest Petroleum University (No. 2017CXTD05).

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-1H,3'H-spiro[chromene[2,3-c]pyrazole-4,1'-isobenzofuran]-3'-one (1e) and 1-(4-chlorophenyl)-7-(dibutylamino)-3-methyl-1H,3'H-spiro[chromene[2,3-c]pyrazole-4,1'-isobenzofuran]-3'-one (1j) have potential as pH indicators for strong acids and bases.

Key words: spiro[chromo(2,3-c)pyrazole-4,1'-isobenzofuran]-3'-one, pyrazolone, Knoevenagel reaction, pH