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

[41] Synthesis of 1-/2-substituted-[1,2,3]triazolo[4,5-g]phthalazine4,9-diones and evaluation of their cytotoxicity and topoisomerase II inhibition
Kim, Jin Sung
Rhee, Hee-Kyung
Park, Hyen Joo
Lee, Sang Kook
Lee, Chong-Ock
Choo, Hea-Young Park
[J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2008, 16 (08) : 4545 - 4550
[42] A new synthesis of indolo[2,3-b]quinolines from 3-acetyl-N-alkyl-2-chloroindoles with 2-aminobenzophenone
Zhang, Hong
Jiang, Yunhe
Sun, Xiaoxue
Liang, Tianyu
Wang, Xiang
Li, Yang
[J]. RSC ADVANCES, 2024, 14 (42) : 30707 - 30712
[43] Synthesis of 2,5-Asymmetrically Substituted 3,4-Diaminothieno[2,3-b]thiophenes by Domino Reaction
Zubarev, Andrey A.
Larionova, Natalia A.
Rodinovskaya, Lyudmila A.
Mortikov, Valery Yu.
Shestopalov, Anatoliy M.
[J]. ACS COMBINATORIAL SCIENCE, 2013, 15 (10) : 546 - 550
[44] One-Step Synthesis of 1H-1,2,3-Triazol-1-Ylmethyl-2,3-Dihydronaphtho[1,2-b]furan-4,5-Diones
Chipoline, Ingrid C.
Ferreira, Vitor F.
da Silva, Fernando de C.
[J]. CURRENT ORGANIC SYNTHESIS, 2015, 12 (05) : 565 - 569
[45] Synthesis of Novel Pyrano[2,3-b]pyridines from ,-Bis(substituted-benzylidene)cycloalkanones
Bigdeli, Mohammad Ali
Marjani, Katayon
Farokhi, Elinaz
Sheikhhosseini, Enayatollah
Ghazanfari, Dadkhoda
[J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 2013, 50 (03) : 625 - 629
[46] A Facile One-Pot Synthesis of Substituted Thieno[2,3-b]pyridines from Enaminones
Gao, Baochang
Dong, Dewen
Zhang, Jie
Ding, Changjiang
Dong, Chunming
Liang, Yongjiu
Zhang, Rui
[J]. SYNTHESIS-STUTTGART, 2012, 44 (02): : 201 - 206
[47] Discovery of antitumor anthra[2,3-b]furan-3-carboxamides: Optimization of synthesis and evaluation of antitumor properties
Shchekotikhin, Andrey E.
Dezhenkova, Lyubov G.
Tsvetkov, Vladimir B.
Luzikov, Yuri N.
Volodina, Yulia L.
Tatarskiy, Victor V., Jr.
Kalinina, Anastasia A.
Treshalin, Michael I.
Treshalina, Helen M.
Romanenko, Vladimir I.
Kaluzhny, Dmitry N.
Kubbutat, Michael
Schols, Dominique
Pommier, Yves
Shtil, Alexander A.
Preobrazhenskaya, Maria N.
[J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2016, 112 : 114 - 129
[48] New antitumor anthra[2,3-b]furan-3-carboxamides: Synthesis and structure-activity relationship
Tikhomirov, Alexander S.
Lin, Chia-Yang
Volodina, Yulia L.
Dezhenkova, Lyubov G.
Tatarskiy, Victor V.
Schols, Dominique
Shtil, Alexander A.
Kaur, Punit
Chueh, Pin Ju
Shchekotikhin, Andrey E.
[J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2018, 148 : 128 - 139
[49] Substituted N-(thieno[2,3-b]pyridine-3-yl)acetamides: synthesis, reactions, and biological activity
Dotsenko, Victor V.
Buryi, Dmitrii S.
Lukina, Darya Yu
Stolyarova, Angelica N.
Aksenov, Nicolai A.
Aksenova, Inna, V
Strelkov, Vladimir D.
Dyadyuchenko, Lyudmila, V
[J]. MONATSHEFTE FUR CHEMIE, 2019, 150 (11): : 1973 - 1985
[50] Synthesis of 6-Substituted 6H-Indolo[2,3-b]quinolines from Isoindigos
Fan, Ling
Liu, Meilin
Ye, Yu
Yin, Guodong
[J]. ORGANIC LETTERS, 2017, 19 (01) : 186 - 189

← 1 2 3 4 5 →