Convenient Synthesis of 2-Amino-4H-chromenes from Photochemically Generated o-Quinone Methides and Malononitrile

被引：18

作者：

Fujiwara, Makoto ^{[1
]}

Sakamoto, Masanori ^{[1
]}

Komeyama, Kimihiro ^{[1
]}

Yoshida, Hiroto ^{[1
]}

Takaki, Ken ^{[1
]}

机构：

[1] Hiroshima Univ, Grad Sch Engn, Dept Appl Chem, Higashihiroshima 7398527, Japan

来源：

JOURNAL OF HETEROCYCLIC CHEMISTRY | 2015年 / 52卷 / 01期

关键词：

AQUEOUS-MEDIA; MANNICH-BASES; 2-AMINO-2-CHROMENES; DERIVATIVES;

D O I：

10.1002/jhet.1964

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2-Amino-4H-chromenes were synthesized in moderate to good yields by the reaction of o-quinone methides photochemically generated from o-(dimethylaminomethyl)phenols with malononitrile. This method was applicable to the synthesis of fluorinated chromenes that were difficult to obtain by other methods. In addition, o-(hydroxymethyl)phenols could be used for the reaction in the presence of tertiary amine bases.

引用

页码：59 / 66

页数：8

共 50 条

[31] MULTI-COMPONENT SYNTHESIS OF 2-AMINO-4H-CHROMENES CATALYZED BY NANO ZnO IN WATER
Hosseini-Sarvari, Mona
Shafiee-Haghighi, Sara
COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 2011, 76 (11) : 1285 - 1298
[32] Mesolite: An Efficient Heterogeneous Catalyst for One-Pot Synthesis of 2-Amino-4H-chromenes
Pawar, Ganesh T.
Magar, Rameshwar R.
Lande, Machhindra K.
POLYCYCLIC AROMATIC COMPOUNDS, 2018, 38 (01) : 75 - 84
[33] Synthesis and characterization of functionalized nano NaY zeolite with metformin and use for the synthesis of 2-amino-4H-chromenes
Haghdadi, Niloofar
Asghari, Sakineh
Pasha, Ghasem Firouzzadeh
RESEARCH ON CHEMICAL INTERMEDIATES, 2024, 50 (05) : 1961 - 1992
[34] Aqua mediated synthesis of substituted 2-amino-4H-chromenes and in vitro study as antibacterial agents
Kidwai, M
Saxena, S
Khan, MKR
Thukral, SS
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2005, 15 (19) : 4295 - 4298
[35] A synergetic role of Aegle marmelos fruit ash in the synthesis of biscoumarins and 2-amino-4H-chromenes
Patil, Rupesh C.
Shinde, Sachinkumar K.
Patil, Uttam P.
Birajdar, Appasaheb T.
Patil, Suresh S.
RESEARCH ON CHEMICAL INTERMEDIATES, 2021, 47 (04) : 1675 - 1691
[36] A Concise Synthesis of 2-(2-Hydroxyphenyl)acetonitriles via the o-Quinone Methides Generated from 2-(1-Tosylalkyl)phenols
Wu, Bo
Gao, Xiang
Chen, Mu-Wang
Zhou, Yong-Gui
CHINESE JOURNAL OF CHEMISTRY, 2014, 32 (10) : 981 - 984
[37] A synergetic role of Aegle marmelos fruit ash in the synthesis of biscoumarins and 2-amino-4H-chromenes
Rupesh C. Patil
Sachinkumar K. Shinde
Uttam P. Patil
Appasaheb T. Birajdar
Suresh S. Patil
Research on Chemical Intermediates, 2021, 47 : 1675 - 1691
[38] Mg(ClO4)2-catalyzed one-pot synthesis of 2-amino-4H-chromenes and dihydropyrano[c]chromenes
Emtiazi, H.
Amrollahi, M. A.
BULGARIAN CHEMICAL COMMUNICATIONS, 2017, 49 (02): : 478 - 482
[39] Pt(IV)-catalyzed generation and [4+2]-cycloaddition reactions of o-quinone methides
Radomkit, Suttipol
Sarnpitak, Pakornwit
Tummatorn, Jumreang
Batsomboon, Paratchata
Ruchirawat, Somsak
Ploypradith, Poonsakdi
TETRAHEDRON, 2011, 67 (21) : 3904 - 3914
[40] NHC-catalyzed stereoselective synthesis of spirooxindole lactones from in situ generated oxindole-embedded o-quinone methides and aldehydes
Cao, Zhengqiang
Hu, Fang
Chu, Yunpeng
Pei, Jiaxue
Hui, Xin-Ping
ORGANIC CHEMISTRY FRONTIERS, 2024, 11 (12) : 3326 - 3332

← 1 2 3 4 5 →