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

被引：13
|
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
下载
收藏
页码：31 / 37
页数：7
相关论文
共 50 条
  • [1] Antioxidant activity of 5,8-dihydroxy-1,4-dihydro-1,4-methanonaphthalene
    A. K. Mitra
    V. B. Gawandi
    K. George
    H. Mohan
    T. Mukherjee
    Research on Chemical Intermediates, 2008, 34 : 85 - 92
  • [2] Antioxidant activity of 5,8-dihydroxy-1,4-dihydro-1,4-methanonaphthalene
    Mitra, A. K.
    Gawandi, V. B.
    George, K.
    Mohan, H.
    Mukherjee, T.
    RESEARCH ON CHEMICAL INTERMEDIATES, 2008, 34 (01) : 85 - 92
  • [3] FLUORINATION OF NORBORNADIENE AND 1,4-DIHYDRO-1,4-METHANONAPHTHALENE WITH SUBSTITUTED (DIFLUOROIODO) BENZENES
    GREGORCIC, A
    ZUPAN, M
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1977, (12): : 1446 - 1449
  • [4] Investigations on the antioxidant activity of 5,8-dihydroxy-1,4-dihydro-1,4-methanonaphthalene (DDMN)
    Mitra, A. K.
    Gawandi, V. B.
    George, K.
    Mohan, H.
    Mukherjee, T.
    RESEARCH ON CHEMICAL INTERMEDIATES, 2009, 35 (01) : 13 - 20
  • [5] Investigations on the antioxidant activity of 5,8-dihydroxy-1,4-dihydro-1,4-methanonaphthalene (DDMN)
    A. K. Mitra
    V. B. Gawandi
    K. George
    H. Mohan
    T. Mukherjee
    Research on Chemical Intermediates, 2009, 35 : 13 - 20
  • [6] SYNTHESIS AND STRUCTURE OF 1,4-DIHYDRO-1,4-DIPHOSPHININES AND 1,4-DIHYDRO-1,4-PHOSPHARSININES
    MARKL, G
    WEBER, W
    WEISS, W
    CHEMISCHE BERICHTE-RECUEIL, 1985, 118 (06): : 2365 - 2395
  • [7] A simple procedure for preparing annulated p-benzoquinones.: Improved synthesis of 1,4-dihydro-1,4-methanonaphthalene-5,8-dione
    Marchand, AP
    Alihodzic, S
    Shukla, R
    SYNTHETIC COMMUNICATIONS, 1998, 28 (03) : 541 - 546
  • [8] Synthesis and Characterization of Stereoisomers of 1,4-Dihydro-1,4-diarsinines
    Arita, Manabu
    Naka, Kensuke
    Morisaki, Yasuhiro
    Nakahashi, Akiko
    Chujo, Yoshiki
    ORGANOMETALLICS, 2009, 28 (20) : 6109 - 6113
  • [9] SYNTHESIS, REACTIVITY, AND LIGAND PROPERTIES OF 1,4-DIHYDRO-1,4-DIBORANAPHTHALENE AND 2,3-BENZO-1,4-DIHYDRO-1,4-DIBORAFULVENE DERIVATIVES
    FESSENBECKER, A
    SCHULZ, H
    PRITZKOW, H
    SIEBERT, W
    CHEMISCHE BERICHTE, 1990, 123 (12) : 2273 - 2278
  • [10] Synthesis of 1,4-dialkyl-1,4-dihydro-1,4-benzo[e]diazepine-5-ones
    Wang, TS
    Cloudsdale, IS
    SYNTHESIS-STUTTGART, 2000, (02): : 265 - 268
12345