Efficient Synthesis of 2,3‐Disubstituted‐1,3‐benzoxazines by Chlorotrimethylsilane‐Mediated Aza‐Acetalizations of Aromatic Aldehydes
Efficient Synthesis of 2,3‐Disubstituted‐1,3‐benzoxazines by Chlorotrimethylsilane‐Mediated Aza‐Acetalizations of Aromatic Aldehydes
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DOI：
10.1002/jhet.1590
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发表时间：
2013-09
影响因子：
2.4
通讯作者：
Zi-long Tang;Zhonghua Zhu;Lin Yan;Shuhong Chang;Hanwen Liu
中科院分区：
文献类型：
--
作者：
Zi-long Tang;Zhonghua Zhu;Lin Yan;Shuhong Chang;Hanwen Liu
以3，4-二氢-2H-1，3-苯并恶嗪为原料，在氯三甲基硅烷或SnCl4存在下，通过芳醛与2-(N-取代氨基甲基)苯酚的氮合缩合反应合成了一系列新型取代的3，4-二氢-2H-1，3-苯并恶嗪。结果表明，氯三甲基硅烷对该反应尤其是对氟苯甲醛的反应更为有效，为3，4-二氢-2H-1，3-苯并恶嗪的合成提供了一种有效的方法。化合物的结构经红外光谱、核磁共振氢谱、核磁共振碳谱、质谱图和元素分析确证。
A series of novel substituted 3,4-dihydro-2H-1,3-benzoxazines were prepared in moderate to good yields by aza-acetalizations of aromatic aldehydes with 2-(N-substituted aminomethyl)phenols in the presence of chlorotrimethylsilane or SnCl4. It was found that chlorotrimethylsilane was more effective for the reaction, especially for the reaction of fluorobenzaldehyde, and thereby, an efficient method for the preparation of 3,4-dihydro-2H-1,3-benzoxazines was developed. The structures of the compounds were determined by FT-IR, 1H NMR, 13C NMR, MS, and elemental analysis.