Selective Synthesis of Cyano-Functionalized 2-Aryl-4H-chromenes and 2-Amino-4H-chromene-3-carbonitriles by Catalyst-Tuned Reactions of 2-Hydroxychalcones with 2-Substituted Acetonitriles

被引：18

作者：

Yin, Guodong ^{[1
]}

Shi, Houqiang ^{[1
]}

Xu, Liqianyun ^{[1
]}

Wei, Xianhong ^{[1
]}

Tao, Qing ^{[1
]}

机构：

[1] Hubei Normal Univ, Hubei Key Lab Pollutant Anal & Reuse Technol, Coll Chem & Environm Engn, Huangshi 435002, Peoples R China

来源：

SYNTHESIS-STUTTGART | 2013年 / 45卷 / 03期

基金：

中国国家自然科学基金;

关键词：

heterocycles; nitriles; catalysis; chromenes; ONE-POT SYNTHESIS; EFFICIENT ACCESS; DERIVATIVES; APOPTOSIS; SALICYLALDEHYDES; MALONONITRILE; 4H-CHROMENES; PROTEIN; 2-IMINO; DESIGN;

D O I：

10.1055/s-0032-1317945

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A selective synthesis of 4H-chromenes by the reactions of 2-hydroxychalcone derivatives with acetonitriles substituted with electron-withdrawing groups is described. Under catalyst-free conditions, the reactions give cyano-functionalized 2-aryl-4H-chromenes, whereas in the presence of sodium bicarbonate, 2-amino-4H-chromene-3-carbonitriles are obtained in excellent yields.

引用

页码：334 / 340

页数：7

共 35 条

[1] Aminocyanopyridine inhibitors of mitogen activated protein kinase-activated protein kinase 2 (MK-2)
Anderson, DR
Hegde, S
Reinhard, E
Gomez, L
Vernier, WF
Lee, L
Liu, S
Sambandam, A
Snider, PA
Masih, L
[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2005, 15 (06) : 1587 - 1590
[2] Enantioselective One-Pot Synthesis of 2-Amino-4-(indol-3-yl)-4H-Chromenes
Chen, Weiliang
Cai, Yunfei
Fu, Xuan
Liu, Xiaohua
Lin, Lili
Feng, Xiaoming
[J]. ORGANIC LETTERS, 2011, 13 (18) : 4910 - 4913
[3] The condensation of salicylaldehydes and malononitrile revisited:: Synthesis of new dimeric chromene derivatives
Costa, Marta
Areias, Filipe
Abrunhosa, Luis
Venancio, Armando
Proenca, Fernanda
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (05) : 1954 - 1962
[4] Potassium exchanged layered zirconium phosphate as catalyst in the preparation of 4H-chromenes
Curini, M
Epifano, F
Chimichi, S
Montanari, F
Nocchetti, M
Rosati, O
[J]. TETRAHEDRON LETTERS, 2005, 46 (20) : 3497 - 3499
[5] Simple, Efficient, and Catalyst-Free Synthesis of (2-Amino-4H-1-benzopyran-4-yl)phosphonates in Polyethylene Glycol
Das, Biswanath
Balasubramanyam, Penagaluri
Reddy, Gandollo Chinna
Salvanna, Nayaki
[J]. HELVETICA CHIMICA ACTA, 2011, 94 (07) : 1347 - 1350
[6] An ecofriendly approach to the synthesis of 2-imino- and 2-oxo-3-phenylsulfonyl-2H-chromenes
Dias, Tatiana A.
Fernanda Proenca, M.
[J]. TETRAHEDRON LETTERS, 2012, 53 (39) : 5235 - 5237
[7] Enantioselective organocatalytic synthesis of medicinally privileged 2-amino-4H-chromene-3-carbonitriles via a cascade process
Du, Zhiyun
Siau, Woon-Yew
Wang, Jian
[J]. TETRAHEDRON LETTERS, 2011, 52 (46) : 6137 - 6141
[8] Catalysis of salicylaldehydes and two different C-H acids with electricity:: First example of an efficient multicomponent approach to the design of functionalized medicinally privileged 2-Amino-4H-Chromene scaffold
Elinson, Michail N.
Dorofeev, Alexander S.
Miloserdov, Fedor M.
Ilovalsky, Alexey I.
Feducovich, Sergey K.
Belyakov, Pavel A.
Nikishin, Gennady I.
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (04) : 591 - 601
[9] Solvent-free cascade reaction: direct multicomponent assembling of 2-amino-4H-chromene scaffold from salicylaldehyde, malononitrile or cyanoacetate and nitroalkanes
Elinson, Michail N.
Ilovaisky, Alexey I.
Merkulova, Valentina M.
Belyakov, Pavel A.
Chizhov, Alexander O.
Nikishin, Gennady I.
[J]. TETRAHEDRON, 2010, 66 (23) : 4043 - 4048
[10] Unexpected C-C Bond Cleavage: A Route to 3,6-Diarylpyridazines and 6-Arylpyridazin-3-ones from 1,3-Dicarbonyl Compounds and Methyl Ketones
Gao, Qinghe
Zhu, Yanping
Lian, Mi
Liu, Meicai
Yuan, Jingjing
Yin, Guodong
Wu, Anxin
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (21) : 9865 - 9870

← 1 2 3 4 →