Silver(I)-Catalyzed Tandem Sigamatropic Rearrangement/1,3‑H Shift/ 6π Aza-electrocyclization of N‑Propargylic Hydrazones: A Mild Synthetic Route to 1,6-Dihydropyridazines

Silver(I)-Catalyzed Tandem Sigamatropic Rearrangement/1,3‑H Shift/ 6 π Aza-electrocyclization of N‑Propargylic Hydrazones: A Mild Synthetic Route to 1,6-Dihydropyridazines

Zong-Cang Ding, Lu-Chuan Ju, Ying Yang, Xiao-Ming An, Yun-Bing Zhou, Ren-Hao Li, Hai-Tao Tang, Cheng-Ke Ding, and Zhuang-Ping Zhan*

 

Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, Fujian, P. R. China

J. Org. Chem. DOI: 10.1021/acs.joc.6b00428

TOC:

Abstract:

A highly efficient AgOTf catalyzed [3,3]

sigmatropic rearrangement/1,3-H shift/6π aza-electrocycliza-

tion cascade reaction of N-propargylic hydrazones has been

developed. This method provides a new mild synthetic route

to various polysubstituted 1,6-dihydropyridazines including the

3-CF3-substituted ones with high selectivity.