Base-Promoted [4 + 1 + 1] Multicomponent Tandem Cycloaddition of Ortho-Substituted Nitroarenes, Aldehydes, and
Guiyun Zeng1, Juan Wan1, Yilong Yuan1
1Key Laboratory of Biomass Green Chemical Conversion of Yunnan Provincial Education Department, Yunnan Key La-boratory of Chiral Functional Substance Research and Application, School of Chemistry & Environment, Yunnan Minzu University, Kunming 650504, P. R. China.
Abstract:
We report a base-promoted, metal-free multicomponent tandem reaction, involving a [4 + 1 + 1] cycloaddition process between ortho-substituted nitroarenes, aldehydes, and ammonium salts. Modifying the substituents on the nitroaromatic compounds effectively provides structurally diverse 2-substituted and 4-alkenylquinazolines with good to excellent yields (77%-90% and quinazoline 51 examples) and high tolerance for various inorganic ammonium salts (13 examples, such as NH3·H2O, NH4Cl, and NH4HF2). A new method for constructing 2,4-substituted quinazoline compounds with high selectivity from simple nitrogen source compounds was developed, and the reaction can be scaled up to a gram scale. Additionally, this method also facilitates the preparation of organic molecules with photophysical properties, offering new insights into the further transformation of quinazolines.
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