Lu Yuling, Duan Xianxian, Chen Xia, Yao Meng, Chen Chunmei, Zhu Hucheng, Luo Zengwei, Zhang Yonghui
Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation. School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, P. R. China.
Org Biomol Chem. 2022 Apr 13;20(15):3174-3182. doi: 10.1039/d2ob00121g.
The thermal tetradehydro-Diels-Alder (TDDA) reaction for the synthesis of polysubstituted aromatic compounds remains underestimated probably due to the harsh conditions and multiproduct results. Herein, a mild intramolecular TDDA reaction of aryldiyne compounds is presented with linear naphthalenes only, exhibiting good functional group tolerance. The reaction is easy to operate and amenable to multigram-scale synthesis. From the preliminary work, it was found that the mild conditions may be the key to the completely linear product in the reactions.
用于合成多取代芳香族化合物的热四脱氢狄尔斯-阿尔德（TDDA）反应可能由于条件苛刻和产物多样而一直未得到充分重视。在此，我们报道了芳基二炔化合物的温和分子内TDDA反应，该反应仅生成线性萘，具有良好的官能团耐受性。该反应操作简便，适用于多克规模的合成。从初步工作中发现，温和的条件可能是反应中得到完全线性产物的关键。
