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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

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, Email: zpzhanxmu.edu.cn

Z.-C. Ding, L-C. Ju, Y. Yang, X.-M. An, Y.-B. Zhou, R.-H. Li, H.-T. Tang, C.-K. Ding, Z.-P. Zhan, J. Org. Chem., 2016, 81, 3936-3941.

DOI: 10.1021/acs.joc.6b00428 (free Supporting Information)


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Abstract

A mild and highly efficient AgOTf catalyzed [3,3] sigmatropic rearrangement/1,3-H shift/6π aza-electrocyclization cascade reaction of N-propargylic hydrazones provides arious polysubstituted 1,6-dihydropyridazines with high selectivity.

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plausible mechanism



Key Words

N-heterocycles


ID: J42-Y2016