以森田-贝里斯-希尔曼(MBH)碳酸酯为原料合成多取代1,4-二氢喹啉类衍生物
收稿日期: 2020-08-12
修回日期: 2020-09-08
网络出版日期: 2020-09-30
基金资助
西南民族大学中央高校基本科研业务费专项资金(2018NQN35)
Synthesis of Multi-substituted 1,4-Dihydroquinoline Derivatives from Morita-Baylis-Hillman (MBH) Carbonates
Received date: 2020-08-12
Revised date: 2020-09-08
Online published: 2020-09-30
Supported by
the Fundamental Research Funds for the Central Universities, Southwest Minzu University(2018NQN35)
以森田-贝里斯-希尔曼(MBH)碳酸酯和活泼亚甲基类化合物为原料, 在叔胺的催化下, 经历两次亲核取代反应得到关键叠氮中间体, 再与三苯基膦作用经连续的Staudinger反应、分子内aza-Wittig反应及异构化等, 在温和的反应条件下合成了17个新的多取代1,4-二氢喹啉类衍生物. 中间体及目标化合物均为新化合物, 其结构均经红外光谱、高分辨质谱、核磁共振氢谱和核磁共振碳谱确证.
关键词： 1,4-二氢喹啉; 氮杂Wittig反应; MBH碳酸酯; 叠氮化物
史鸿燕 , 钟莹 , 赵志刚 . 以森田-贝里斯-希尔曼(MBH)碳酸酯为原料合成多取代1,4-二氢喹啉类衍生物[J]. 有机化学, 2021 , 41(2) : 677 -687 . DOI: 10.6023/cjoc202008020
Using Morita-Baylis-Hillman (MBH) carbonates and active methylene compounds as raw materials, the key azide intermediates were obtained through two nucleophilic substitution reactions catalyzed by tertiary amine. Then, seventeen new multi-substituted 1,4-dihydroquinoline derivatives were obtained by sequential Staudinger/intramolecular aza-Wittig/isomeri- zation reactions of the azide intermediates with triphenylphosphine under mild conditions. The intermediates and target compounds are all new compounds, and their structures have been confirmed by IR, HRMS, 1H NMR and 13C NMR techniques.
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