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Short Paper | Regular issue | Vol 106, No. 9, 2023, pp.1570-1579
Published online, 30th August, 2023
DOI: 10.3987/COM-23-14889
A Convenient Synthesis of 1,2,4-Triazino[2,3-b]indazol-3-amine Derivatives via Tandem Abnormal Staudinger/Aza-Wittig/Isomerization Reaction

Hai Xie,* Xiu-Ting Qin, Ji Li, Ya-Li Zhang, Jin-Yu Li, and Lei Zhang*

*College of Chemistry and Chemical Engineering, Shanxi Datong University, Datong, 037009, People’s Republic of China


A Convenient synthesis route of 1,2,4-triazino[2,3-b]indazol-3-amine analogs by iminophosphoranes with in situ generated from acrylamide containing azide and imino groups and tributylphosphine is herein described. This annulation reaction proceeds through a tandem abnormal Staudinger reaction, intramolecular aza-Wittig reaction and isomerization reaction. This operating procedure has the advantages of simple, cheap and easily available starting materials, mild reaction conditions, no catalyst required, simple operation, and good yield (78-86%). The structures of the synthesized compounds were confirmed by IR, NMR, HRMS and X-ray diffraction.