Citation: Yue Yongshuang, Xie Zhengfeng, Chu Yicheng, Xue Songsong. Synthesis and Optical Properties of Novel Spiro[chromo(2, 3-c)-pyrazole-4, 1'-isobenzofuran]-3'-one Compounds[J]. Chinese Journal of Organic Chemistry, ;2020, 40(2): 501-510. doi: 10.6023/cjoc201907033 shu

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

Oil&Gas Field Applied Chemistry Key Laboratory of Sichuan Province, College of Chemistry and Chemical Engineering, Southwest Petroleum University, Chengdu 610500

Corresponding author: Xie Zhengfeng, xiezhf@swpu.edu.cn
Received Date: 24 July 2019
Revised Date: 9 September 2019
Available Online: 9 February 2019
Fund Project: Project supported by the Youth Science and Technology Innovation Team of Southwest Petroleum University (No. 2017CXTD05)Project supported by the Youth Science and Technology Innovation Team of Southwest Petroleum University No. 2017CXTD05

Figures(8)

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