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

页码：31 / 37

页数：7

共 35 条

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