Synlett, Table of Contents Synlett 2020; 31(01): 73-76DOI: 10.1055/s-0037-1610737 letter © Georg Thieme Verlag Stuttgart · New York One-Pot Synthesis of [1,2,3]Triazolo[1,5-a]quinoxalin-4(5H)-ones by a Metal-Free Sequential Ugi-4CR/Alkyne–Azide Cycloaddition Reaction Yan-Mei Yan a Department of Chemistry, Taiyuan Normal University, Jinzhong 030619, P. R. of China , Hao-Yang Li a Department of Chemistry, Taiyuan Normal University, Jinzhong 030619, P. R. of China , Min Zhang a Department of Chemistry, Taiyuan Normal University, Jinzhong 030619, P. R. of China , Rong-Xin Wang a Department of Chemistry, Taiyuan Normal University, Jinzhong 030619, P. R. of China , Chen-Guang Zhou a Department of Chemistry, Taiyuan Normal University, Jinzhong 030619, P. R. of China , Zhen-Xing Ren∗ b Institute of Applied Chemistry, Shanxi University, Taiyuan 030006, P. R. of China Email: zxren@sxu.edu.cn , Ming-Wu Ding ∗ c Central China Normal University, Wuhan 430079, P. R. of China Email: mwding@mail.ccnu.edu.cn › Author Affiliations Recommend Article Abstract Buy Article All articles of this category Abstract A convenient and one-pot approach to prepare [1,2,3]triazolo[1,5-a]quinoxalin-4(5H)-ones by a metal-free sequential Ugi-4CR/alkyne–azide cycloaddition reaction has been developed. The reaction of 2-azidobenzenamines, aldehydes, propiolic acids, and isocyanides produced the Ugi adducts, which were transformed to the [1,2,3]triazolo[1,5-a]quinoxalin-4(5H)-ones in moderate to good yields via alkyne–azide cycloaddition reaction. Key words Key wordsone-pot - metal-free - [1,2,3]triazolo[1,5-a]quinoxalin-4(5H)-one - Ugi reaction - alkyne–azide cycloaddition reaction Full Text References References and Notes 1a Rotstein BH, Zaretsky S, Rai V, Yudin AK. Chem. Rev. 2014; 114: 8323 1b Dömling A, Wang W, Wang K. Chem. Rev. 2012; 112: 3083 1c Touré BB, Hall DG. Chem. Rev. 2009; 109: 4439 2a Zhu J, Bienaymé H. Multicomponent Reactions. 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After the solvent was evaporated under vacuum, the residue was purified by recrystallization (diethyl ether/petroleum ether = 1:10, v/v) to afford 6. 25 Compound 6a: white solid (yield 412 mg, 85%); mp 236–237 °C. 1H NMR (600 MHz, CDCl3): δ = 8.54 (s, 1 H, Ar-H), 8.31 (d, J = 7.2 Hz, 2 H, Ar-H), 7.49–7.33 (m, 10 H, Ar-H), 6.69 (s, 1 H, NH), 5.86 (d, J = 10.8 Hz, 1 H, CH), 1.32 (s, 9 H, 3 CH3) ppm. 13C NMR (100 MHz, CDCl3): δ = 165.9, 155.1, 149.3, 134.5, 132.2, 129.5, 129.3, 129.2, 129.0, 128.9, 128.7, 128.3, 124.8, 122.5, 121.2, 118.1, 117.0, 52.3, 28.5, 18.4 ppm. HRMS (ESI): m/z [M + H]+ calcd for C27H25ClN5O2: 486.1691; found: 486.1694. Supplementary Material Supplementary Material Supporting Information
