Synthesis of Novel Trisubstituted Olefin-Type Probe Molecules Containing <i>N</i>-Heterocycles and Their Application in Detection of Malononitrile
Zhao-Hua Chen,
Shi-Wei Yu,
Wen-Jin Xu,
Miao-Xin Li,
Yong Zeng,
Si-Wei Deng,
Jian-Yun Lin,
Zhao-Yang Wang
Affiliations
Zhao-Hua Chen
School of Chemistry, South China Normal University, GDMPA Key Laboratory for Process Control and Quality Evaluation of Chiral Pharmaceuticals, Guangzhou Key Laboratory of Analytical Chemistry for Biomedicine, Key Laboratory of Theoretical Chemistry of Environment, Ministry of Education, Guangzhou 510006, China
Shi-Wei Yu
School of Chemistry, South China Normal University, GDMPA Key Laboratory for Process Control and Quality Evaluation of Chiral Pharmaceuticals, Guangzhou Key Laboratory of Analytical Chemistry for Biomedicine, Key Laboratory of Theoretical Chemistry of Environment, Ministry of Education, Guangzhou 510006, China
Wen-Jin Xu
School of Chemistry, South China Normal University, GDMPA Key Laboratory for Process Control and Quality Evaluation of Chiral Pharmaceuticals, Guangzhou Key Laboratory of Analytical Chemistry for Biomedicine, Key Laboratory of Theoretical Chemistry of Environment, Ministry of Education, Guangzhou 510006, China
Miao-Xin Li
School of Chemistry, South China Normal University, GDMPA Key Laboratory for Process Control and Quality Evaluation of Chiral Pharmaceuticals, Guangzhou Key Laboratory of Analytical Chemistry for Biomedicine, Key Laboratory of Theoretical Chemistry of Environment, Ministry of Education, Guangzhou 510006, China
Yong Zeng
School of Chemistry, South China Normal University, GDMPA Key Laboratory for Process Control and Quality Evaluation of Chiral Pharmaceuticals, Guangzhou Key Laboratory of Analytical Chemistry for Biomedicine, Key Laboratory of Theoretical Chemistry of Environment, Ministry of Education, Guangzhou 510006, China
Si-Wei Deng
School of Chemistry, South China Normal University, GDMPA Key Laboratory for Process Control and Quality Evaluation of Chiral Pharmaceuticals, Guangzhou Key Laboratory of Analytical Chemistry for Biomedicine, Key Laboratory of Theoretical Chemistry of Environment, Ministry of Education, Guangzhou 510006, China
Jian-Yun Lin
School of Chemistry, South China Normal University, GDMPA Key Laboratory for Process Control and Quality Evaluation of Chiral Pharmaceuticals, Guangzhou Key Laboratory of Analytical Chemistry for Biomedicine, Key Laboratory of Theoretical Chemistry of Environment, Ministry of Education, Guangzhou 510006, China
Zhao-Yang Wang
School of Chemistry, South China Normal University, GDMPA Key Laboratory for Process Control and Quality Evaluation of Chiral Pharmaceuticals, Guangzhou Key Laboratory of Analytical Chemistry for Biomedicine, Key Laboratory of Theoretical Chemistry of Environment, Ministry of Education, Guangzhou 510006, China
Recently, the construction of the trisubstituted olefin-type probe molecules has elicited the attention of many researchers. However, the synthesis of the trisubstituted olefin-type probes containing two N-heterocycles simultaneously has been rarely reported. In this study, starting from the inexpensive mucobromic acid 1 and N-heterocyclic compound 2, we first utilized a simple one-step reaction to synthesize a series of trisubstituted olefin-type compounds 3 simultaneously bearing with the structure of two N-heterocyclic rings in the absence of transition metal catalysts with a yield of 62–86%. The optimal reaction conditions were systematically explored, and the structure of the obtained compounds 3 were well characterized with 1H NMR, 13C NMR, X-ray single-crystal and HR-MS. The preliminary observation showed that, in the presence of base, mucobromic acid 1 reacts as its ring-opening structure, and the successive nucleophilic substitution reaction and Michael addition reaction can generate the target product 3. Considering that the aldehyde group in the molecular structure of the trisubstituted olefin-type compounds 3 may react with malononitrile, we carried out some relevant investigations so as to realize the visual detection of malononitrile. Interestingly, among the products, compounds 3a–3c can be prepared in portable test strips through a simple process and used to achieve the naked-eye detection of malononitrile in environmental systems as designed.