Citation: Zhi Bin XU, Zong Ru GUO. An Abnormal Reaction of N-(2,4-dinitrophenyl)-L-proline with Thionyl Chloride[J]. Chinese Chemical Letters, ;2003, 14(2): 133-134. shu

An Abnormal Reaction of N-(2,4-dinitrophenyl)-L-proline with Thionyl Chloride

Zhi Bin XU ,
Zong Ru GUO

Institute of Materia Medica, Chinese Academy of Medical Sciences & Peking Union Medical College, Beijing 100050

Received Date: 15 April 2002

N-(2,4-Dinitrophenyl)-4-amino-n-butyl aldehyde 3 was obtained with high yield of 80% when N-(2,4-dinitrophenyl)-L-proline 1 reacted with SOCl₂ at room temperature.However, the anticipated product N-(2,4-dinitrophenyl)-tetrahydropyrrolyl-2-(4-methylthiophenyl) ketone 2 did not be produced.The mechanism was discussed in this article.
- L-Proline,
- 1-fluoro-2,4-dinitrobenzene(FDNB),
- N-(2,4-dinitrophenyl)-4-amino-n-butylaldehyde
1. [1]
  Xuehua SUN , Min MA , Jianting LIU , Rui TIAN , Hongmei CHAI , Huali CUI , Loujun GAO . Pr/N co-doped biomass carbon dots with enhanced fluorescence for efficient detection of 2,4-dinitrophenylhydrazine. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 561-573. doi: 10.11862/CJIC.20240294
2. [2]
  Junjun Huang , Ran Chen , Yajian Huang , Hang Zhang , Anran Zheng , Qing Xiao , Dan Wu , Ruxia Duan , Zhi Zhou , Fei He , Wei Yi . Discovery of an enantiopure N-[2-hydroxy-3-phenyl piperazine propyl]-aromatic carboxamide derivative as highly selective α_1D/1A-adrenoceptor antagonist and homology modelling. Chinese Chemical Letters, 2024, 35(11): 109594-. doi: 10.1016/j.cclet.2024.109594
3. [3]
  Yang Liu , Jing Liang , Mengzhu Zheng , Haoze Song , Lixia Chen , Hua Li . PD-L1/SHP2 dual PROTACs inhibit melanoma by enhancing T-cell killing activity. Chinese Chemical Letters, 2025, 36(6): 110317-. doi: 10.1016/j.cclet.2024.110317
4. [4]
  Huixian Weng , Lefei Hu , Lei Hu , Yihan Zhou , Aohua Wang , Ning Wang , Wenzhe Li , Chunliu Zhu , Shiyan Guo , Miaorong Yu , Yong Gan . Corrigendum to "The complexation of insulin with sodium N-[8-(2-hydroxybenzoyl)amino]-caprylate for enhanced oral delivery: Effects of concentration, ratio, and pH" [Chinese Chemical Letters 33 (2022) 1889-1894]. Chinese Chemical Letters, 2025, 36(8): 111316-. doi: 10.1016/j.cclet.2025.111316
5. [5]
  Xiu-Mei Xie , Hongyang Zhang , Shao-Xuan Gong , Hong-Xia Sun , Yu-Ting Liu , Xue-Ling Chen , Shuming Chen , Tian-Yu Gao , Wai-Yeung Wong , Zhen Zhang , Da-Gang Yu . Carbonylation of C(sp³)–H bonds with CO₂: Facile synthesis of 2,4-quinolinediones and related luminescent materials. Chinese Chemical Letters, 2026, 37(3): 112003-. doi: 10.1016/j.cclet.2025.112003
6. [6]
  Qiong-Hui Peng , Ning-Bo Li , Jia-Cheng Hou , Cai-Jun He , Ya-Xin Yang , Chun-Lin Zhuang , Li-Juan Ou , Mei Yuan , Wei-Min He . Nd@g-C₃N₄ dual-functional photosynthesis and antitumor activities of 3-fluoroalkylated quinoxalin-2(1H)-ones. Chinese Chemical Letters, 2025, 36(12): 111402-. doi: 10.1016/j.cclet.2025.111402
7. [7]
  An Lu , Yuhao Guo , Yi Yan , Lin Zhai , Xiangyu Wang , Weiran Cao , Zijie Li , Zhixia Zhao , Yujie Shi , Yuanjun Zhu , Xiaoyan Liu , Huining He , Zhiyu Wang , Jian-Cheng Wang . Nanomedicine integrating the lipidic derivative of 5-fluorouracil, miriplatin and PD-L1 siRNA for enhancing tumor therapy. Chinese Chemical Letters, 2024, 35(6): 108928-. doi: 10.1016/j.cclet.2023.108928
8. [8]
  Cong-Bin Ji , Ding-Xiong Xie , Mei Chen , Ye-Ying Lan , Bao-Hua Zhang , Ji-Ying Yang , Zheng-Hui Kang , Shu-Jie Chen , Yu-Wei Zhang , Yun-Lin Liu . Green synthesis of 2-trifluoromethylquinoline skeletons via organocatalytic N-[(α-trifluoromethyl)vinyl]isatins CN bond activation. Chinese Chemical Letters, 2025, 36(7): 110598-. doi: 10.1016/j.cclet.2024.110598
9. [9]
  Shuang Zhao , Fei Jia , Kaibei Zhan , Rui-Xi Wang , Pengfei Tan , Lin Shen , Li-Ming Wu , Ling Chen . Amino substitution strategy achieves significant blue shift while preserving high optical anisotropy: A₂(H₃C₃N₄S₂)₂•H₂O (A =NH₄, K, Rb, Cs). Chinese Chemical Letters, 2026, 37(3): 110625-. doi: 10.1016/j.cclet.2024.110625
10. [10]
  Ting Pan , Dinghu Zhang , Guomei You , Xiaoxia Wu , Chenguang Zhang , Xinyu Miao , Wenzhi Ren , Yiwei He , Lulu He , Yuanchuan Gong , Jie Lin , Aiguo Wu , Guoliang Shao . PD-L1 targeted iron oxide SERS bioprobe for accurately detecting circulating tumor cells and delineating tumor boundary. Chinese Chemical Letters, 2025, 36(1): 109857-. doi: 10.1016/j.cclet.2024.109857
11. [11]
  Hai-Yang Song , Jun Jiang , Yu-Hang Song , Min-Hang Zhou , Chao Wu , Xiang Chen , Wei-Min He . Supporting-electrolyte-free electrochemical [2 + 2 + 1] annulation of benzo[d]isothiazole 1,1-dioxides, N-arylglycines and paraformaldehyde. Chinese Chemical Letters, 2024, 35(6): 109246-. doi: 10.1016/j.cclet.2023.109246
12. [12]
  Yi Zhou , Wei Zhang , Rong Fu , Jiaxin Dong , Yuxuan Liu , Zihang Song , Han Han , Kang Cai . Self-assembly of two pairs of homochiral M₂L₄ coordination capsules with varied confined space using Tröger's base ligands. Chinese Chemical Letters, 2025, 36(2): 109865-. doi: 10.1016/j.cclet.2024.109865
13. [13]
  Xiaofei NIU , Ke WANG , Fengyan SONG , Shuyan YU . Self-assembly of [Pd₆(L)₄]⁸⁺-type macrocyclic complexes for fluorescent sensing of HSO₃^-. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1233-1242. doi: 10.11862/CJIC.20240057
14. [14]
  Qing Zhang , Ling Sun , Lingyu Wu , Xue Wang , Liru Chen , Youyou Chen , Yuhang Liu , Wenhui Gu , Donglei Shi , Wenwen Liu , Jian Li , Yi-You Huang , Baoli Li , Hai-Bin Luo . Platycladus orientalis (L.) Franco demonstrates effective anti-psoriasis effects by inhibiting PDE4 with favorable safety profiles. Chinese Chemical Letters, 2025, 36(10): 110795-. doi: 10.1016/j.cclet.2024.110795
15. [15]
  Ruiyan CHEN , Yanping HE , Jian ZHANG . Synthesis and third-order nonlinear optical property of Ti₄L₆ cage-based metal-organic framework. Chinese Journal of Inorganic Chemistry, 2025, 41(10): 2149-2156. doi: 10.11862/CJIC.20250177
16. [16]
  Xiaopeng Han , Jiayin Li , Fei Li , Zhongyue Yuan , Hao Li , Lei Yang , Yan-Ming Xia , Chao Teng , Chao Qin , Lifang Yin . ROS-sensitive dihydroartemisinin prodrug amplify chemo-immunotherapy efficacy of doxorubicin by coordinating robust tumor cell immunogenic cell death and PD-L1 blockade. Chinese Chemical Letters, 2026, 37(2): 111335-. doi: 10.1016/j.cclet.2025.111335
17. [17]
  Xiaochun Liu , Gaoyan Chen , Xiaodong Yue , Chaoyue Wang , Xue-Xin Zhang , Xuecheng Ran , Yingxiao Zong , Junke Wang , Xicun Wang . A novel N-stable Co₂P nano-catalyst for the synthesis of quinoxalines by annulation of alkynes and 1,2-diaminobenzenes. Chinese Chemical Letters, 2025, 36(8): 110707-. doi: 10.1016/j.cclet.2024.110707
18. [18]
  Yanglin Jiang , Mingqing Chen , Min Liang , Yige Yao , Yan Zhang , Peng Wang , Jianping Zhang . Experimental and Theoretical Investigations of Solvent Polarity Effect on ESIPT Mechanism in 4′-N,N-diethylamino-3-hydroxybenzoflavone. Acta Physico-Chimica Sinica, 2025, 41(2): 100012-0. doi: 10.3866/PKU.WHXB202309027
19. [19]
  Tao Yu , Vadim A. Soloshonok , Zhekai Xiao , Hong Liu , Jiang Wang . Probing the dynamic thermodynamic resolution and biological activity of Cu(Ⅱ) and Pd(Ⅱ) complexes with Schiff base ligand derived from proline. Chinese Chemical Letters, 2024, 35(4): 108901-. doi: 10.1016/j.cclet.2023.108901
20. [20]
  Caixia Lin , Ting Liu , Zhaojiang Shi , Hong Yan , Keyin Ye , Yaofeng Yuan . Innovative Experiment of Electrochemical Dearomative Spirocyclization of N-Acyl Sulfonamides. University Chemistry, 2025, 40(4): 359-366. doi: 10.12461/PKU.DXHX202406107

Get Citation

PDF

XML

Metrics

PDF Downloads(2)
Abstract views(1145)
HTML views(22)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

Address：Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888

DownLoad: Full-Size Img PowerPoint

Return