Continuous-Flow Process for the Synthesis of 5-Nitro-1,4-dihydro-1,4-methanonaphthalene

被引：15
作者：
Tan, Zhiyong [1 ]
Li, Zhenhua [1 ]
Jin, Guoqiang [1 ]
Yu, Chuanming [2 ]
机构：
[1] Zhejiang Univ Technol, Coll Pharmaceut Sci, Minist Educ, Key Lab Green Pharmaceut Technol & Related Equipm, Chao Wang Rd 18, Hangzhou 310014, Zhejiang, Peoples R China
[2] Zhejiang Univ Technol, Collaborat Innovat Ctr Yangtze River Delta Reg, Natl Engn Res Ctr Proc Dev Act Pharmaceut Ingredi, Green Pharmaceut, Hangzhou 310014, Zhejiang, Peoples R China
来源：
ORGANIC PROCESS RESEARCH & DEVELOPMENT | 2019年 / 23卷 / 01期
基金：
中国国家自然科学基金;
关键词：
continuous-flow reaction; isoamyl nitrite; diazotization; Diels-Alder reaction; aryne; ISOAMYL NITRITE; ARYNES; ACID; CHEMISTRY; REACTORS; SCOPE;
D O I：
10.1021/acs.oprd.8b00281
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
In this article, we describe a safe and practical process for the synthesis of 5-nitro-1,4-dihydro-1,4-methanonaphthalene (1) via a continuous-flow reactor. The primary procedures in this process involved not merely the production of isoamyl nitrite but also the temperature-programmed Diels-Alder reaction of an aryne (derived from 2-amino-6-nitrobenzoic acid) with cyclopentadiene in the series flow reactor. The continuous-flow process minimized the accumulation of dangerous isoamyl nitrite and the energetic diazonium salt, and the entire reaction time was held down to 250 s.
引用
收藏
页码：31 / 37
页数：7
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