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JOURNAL OF CHEMICAL RESEARCH · 2013 · IF 0.596

Synthesis of novel spiro[cyclopropane-indolizine] derivatives via magnesium-mediated conjugate addition of bromoform

Bin Liu,Xiaofang Li,Jie Zhang,Liyun Du,Rongjin Zeng

The reaction of 6,7-dihydroindolizin-8(5H)-one and an aromatic aldehyde yielded (E)-7-(arylmethylene)-6,7-dihydroindolizin-8(5H)-ones which underwent addition of bromoform in the presence of magnesium under N2 to give a novel series of 3-aryl-2,2-dibromo-5′H-spiro[cyclopropane-1,7′-indolizin]-8′(6′H)-one derivatives. The structures of the products were established by 1H NMR, 13C NMR, IR spectroscopy and mass spectra.

研究领域: 有机化学 · 药物化学
✓ 已验证 DOI 高影响因子
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JOURNAL OF ORGANIC CHEMISTRY · 2023 · IF 3.6

Copper-Catalyzed Formal [4 + 1] Annulation toward Diverse Trifunctionalized Indolizines from Pyridinium 1,4-Zwitterionic Thiolates and Diazos

Wen Li,Hexiang Wang,Yuan Zhang,Limin Zhao,Pengfeng Guo,Hua Cao,Xiang Liu

Pyridinium 1,4-zwitterionic thiolates were regarded as powerful and versatile building blocks to prepare nitrogen- and sulfur-containing heterocycles. Herein, we reported a copper-catalyzed formal [4 + 1] annulation of pyridinium 1,4-zwitterionic thiolates and diazo compounds without any additives to access a library of trifunctionalized indolizines in good yields. Besides, isoquinolinium 1,4-zwitterionic thiolates and imidazolium 1,4-zwitterionic thiolates were also applied to this formal [4 + 1] annulation reaction. Of particular note is that various functional groups such as −CO2R, −CO2NR2, −CF3, −CN, and −(O)P(OR)2 could be easily introduced into cycloaddition products indolizines by this strategy.

研究领域: 有机化学 · 合成化学
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SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY · 2021 · IF 4.098

Benzoindoxazine derivatives containing carbazole for detection of CN− and its application in plant seed extracts and cell imaging

Wei Pan,Guo-Guo Chen,Zhen-You Zhang,Xiao-Qun Cao,Shi-Li Shen,Xian-Hong Pang,Yan Zhu

Cyanide (CN − ) is a highly toxic compound that exists in many substances and is harmful to the environment and human health. Therefore, it is of great significance to develop excellent CN − ion probes, especially solvent-induced on–off fluorescent probes. Based on the condensation reaction of indolo[2,1-b][1,3]oxazine molecules with aldehydes, probes ( E )-13a-(2-(9-ethyl-9 H -carbazol-3-yl)vinyl)-14,14-dimethyl-10-nitro-13a,14-dihydro-8 H -benzo[e]benzo[5,6][1,3]oxazino[3,2-a]indole (NCO) and ( E )-13a-(2-(9-benzyl-9 H -carbazol-3-yl)vinyl)-14,14-dimethyl-10-nitro-13a,14-dihydro-8 H -benzo[e]benzo[5,6][1,3]oxazino[3,2-a]indole (NBO) were synthesized to detect CN − . Compared with other cyanogen ion probes, NCO and NBO have special carbazole ring structures and large conjugate systems. When CN − is added to the probe-detection solution, color changes that are visible to the naked eye can occur. The UV–vis spectrum test using differential spectroscopy shows that the probe (i) has excellent solvent-induced switching characteristics and stability (CH 3 OH–H 2 O) and (ii) high selectivity, anti-interference ability, and sensitivity for the detection of CN − . The fluorescence limit of detections (LODs) are 1.05 µM for NCO and 1.34 µM for NBO. The UV LODs are 0.83 µM for NCO and 0.87 µM for NBO. Fluorescence spectroscopy shows that the probe has remarkable fluorescence properties. Fluorescence titration experiments, liver cancer cell (Hep G2) imaging, and cytotoxicity experiments all show that the probes have high biocompatibility, low toxicity, high cell permeability, and high sensitivity for the detection of CN − in cells. In addition, NCO and NBO have been successfully used for the detection of cyanogenic glycosides in the seeds of ginkgo, crabapple, apple, and cherry. Test strips were fabricated to detect CN − . After adding CN − , the color of the test strip changed significantly—from brown to light yellow; thus, the test strips have a high application value in the fields of drug quality control, drug safety testing, and pharmacological research.

研究领域: 分析化学 · 生物医学 · 环境科学
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JOURNAL OF ORGANIC CHEMISTRY · 2024 · IF 3.3

Controlled and Site-Selective C–H/N–H Alkenylation, Dialkenylation, and Dehydrogenative β-Alkenylation of Various N-Heterocycles

Jin Yan,Suijie Zhong,Xu Chen,Yihuan Luo,Hua Cao,Xiang Liu,Limin Zhao

Here, we report controlled and site-selective C–H alkenylation and dialkenylation of indolizines and pyrrolo[1,2-a]quinolines with β-alkoxyvinyl trifluoromethylketones under simple and practical conditions. Moreover, this direct C–H alkenylation strategy can also be extended to imidazo[1,2-a]pyridines. Notably, without a transition metal and external oxidant, efficient dehydrogenative β-alkenylation of tertiary amines with β-alkoxyvinyl trifluoromethylketones is presented.

研究领域: 有机化学 · 合成化学
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