Synthesis of 3-Substituted 2-Aminonaphtho[2,3-b]furan-4,9-diones from 2-Hydroxy-1,4-Naphthoquinone and Nitroalkenes

被引：10

作者：

Zanwar, Manoj R. ^{[1
]}

Kavala, Veerababurao ^{[1
]}

Gawande, Sachin D. ^{[1
]}

Kuo, Chun-Wei ^{[1
]}

Kuo, Ting-Shen ^{[1
]}

Chen, Mei-Ling ^{[1
]}

He, Chiu-Hui ^{[1
]}

Yao, Ching-Fa ^{[1
]}

机构：

[1] Natl Taiwan Normal Univ, Dept Chem, Taipei 116, Taiwan

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 2013卷 / 36期

关键词：

Multicomponent reactions; Green chemistry; Quinones; Nitroalkenes; Amines; ORGANIC-REACTIONS; CATALYST-FREE; WATER CHEMISTRY; DERIVATIVES; FURANONAPHTHOQUINONES; CONSTITUENTS; CYTOTOXICITY; SUPPRESSION; DECOMPOSITA; ALKYLATION;

D O I：

10.1002/ejoc.201300996

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The efficient base-catalyzed synthesis of 3-substituted 2-aminonaphtho[2,3-b]furan-4,9-dione derivatives from readily available precursors such as 2-hydroxy-1,4-naphthoquinone and nitroalkenes under aqueous conditions is described. Interesting features of this methodology are the conversion of a nitro functionality into an amino functionality in the absence of a reducing agent and the development of a three component reaction for accessing the same product from an aldehyde, 2-hydroxy-1,4-naphthoquinone and nitromethane.

引用

页码：8288 / 8298

页数：11

共 50 条

[21] Synthesis of naphtho[2,3-b]furan-4,9-diones having a trifluoromethyl group under conditions of phase-transfer catalysis
Davydov, DV
Beletskaya, IP
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 40 (01) : 134 - 136
[22] Synthesis of Naphtho[2,3-b]furan-4,9-diones Having a Trifluoromethyl Group under Conditions of Phase-Transfer Catalysis
D. V. Davydov
I. P. Beletskaya
Russian Journal of Organic Chemistry, 2004, 40 : 134 - 136
[23] DFT calculations and IR studies on 2-hydroxy-1,4-naphthoquinone and its 3-substituted derivatives
Satoh, Takehiko
Tsuji, Takemasa
Matsuda, Hiroko
Sudoh, Susumu
Bulletin of the Chemical Society of Japan, 2007, 80 (02): : 321 - 323
[24] DFT calculations and IR studies on 2-hydroxy-1,4-naphthoquinone and its 3-substituted derivatives
Satoh, Takehiko
Tsuji, Takemasa
Matsuda, Hiroko
Sudoh, Susumu
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2007, 80 (02) : 321 - 323
[25] ONE-STEP SYNTHESIS OF 2,3-DIHYDRONAPHTHO[2,3-B]THIOPHENE-4,9-DIONES BY A NEW REGIOSELECTIVE [3+2]PHOTOADDITION OF PHOTOGENERATED 2-MERCAPTO-1,4-NAPHTHOQUINONE WITH ALKENES
SUGINOME, H
KOBAYASHI, K
KONISHI, A
MINAKAWA, H
SAKURAI, H
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (09) : 807 - 809
[26] A FACILE SYNTHESIS OF 2-ACETYLNAPHTHO[2,3-B]FURAN-4,9-DIONE
KOYANAGI, J
YAMAMOTO, K
NAKAYAMA, K
TANAKA, A
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1995, 32 (04) : 1289 - 1291
[27] Lapachol and isomeric 5-and 8-hydroxy-2-(1'-hydroxyethyl)naphtho[2,3-b] furan-4,9-diones are effective antileishmanial constituents of Tabebuia avellanedae
Ali, A.
Kiderlen, A.
Kolodziej, H.
PLANTA MEDICA, 2010, 76 (12) : 1312 - 1312
[28] PHOTOINDUCED MOLECULAR-TRANSFORMATION .120. NEW ONE-STEP GENERAL-SYNTHESIS OF 2,3-DIHYDRONAPHTHO[2,3-B]FURAN-4,9-DIONES BY REGIOSELECTIVE PHOTOADDITION OF 2-HYDROXY-1,4-NAPHTHOQUINONES WITH VARIOUS ALKENES AND ITS APPLICATION TO A 2-STEP SYNTHESIS OF MATURINONE
KOBAYASHI, K
SHIMIZU, H
SASAKI, A
SUGINOME, H
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (10): : 3204 - 3205
[29] Visible-light-mediated synthesis, NMR analysis and X-ray crystal structure of naphtho[2,3-b]furan-4,9-diones
Tan, Hong-bo
Zhang, Xu
Xiang, Yu-heng
Huang, Jing-wen
Xu, Zhi-gang
Tang, Dian-yong
Chen, Zhong-zhu
Wang, Bo-chu
JOURNAL OF MOLECULAR STRUCTURE, 2023, 1292
[30] A facile, three-component domino protocol for the microwave-assisted synthesis of functionalized naphtho[2,3-b]furan-4,9-diones in water
Prasanna, Pitchaimani
Balamurugan, Kamaraj
Perumal, Subbu
Carlos Menendez, J.
GREEN CHEMISTRY, 2011, 13 (08) : 2123 - 2129

← 1 2 3 4 5 →