Synthesis of Functionalized Benzo[b]furans via Oxidative Cyclization of o-Cinnamyl Phenols

被引：24

作者：

Rehan, Mohammad ^{[1
]}

Nallagonda, Rajender ^{[1
]}

Das, Braja Gopal ^{[1
]}

Meena, Tannu ^{[1
]}

Ghorai, Prasanta ^{[1
]}

机构：

[1] Indian Inst Sci Educ & Res Bhopal, Dept Chem, Bhopal 462066, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 82卷 / 07期

关键词：

ONE-POT SYNTHESIS; ASSISTED INTRAMOLECULAR AMINATION; PALLADIUM-CATALYZED SYNTHESIS; UNACTIVATED INTERNAL ALKYNES; METAL-FREE SYNTHESIS; IN-VITRO EVALUATION; ALLYLIC ALCOHOLS; C-H; BENZOFURAN DERIVATIVES; 2,3-DISUBSTITUTED BENZOFURANS;

D O I：

10.1021/acs.joc.6b02752

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Disclosed herein is an efficient synthetic route for the synthesis of functionalized 2-benzyl benzo[b]furans via a regioselective 5-exo-trig intramolecular oxidative cyclization of ortho-cirinamyl phenols using [PdCl2(CH3CN)2] as catalyst and benzoquinone as an oxidant. Further, a sequential ortho-cinnamylation of phenols using cinnamyl alcohols catalyzed by Re2O7, followed by an oxidative cyclization using the above Pd catalyst, is performed. The reaction showed broad substrate scope with good to excellent yields.

引用

页码：3411 / 3424

页数：14

共 50 条

[21] Direct Access to Benzo[b]furans through Palladium-Catalyzed Oxidative Annulation of Phenols and Unactivated Internal Alkynes
Kuram, Malleswara Rao
Bhanuchandra, M.
Sahoo, Akhila K.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (17) : 4607 - 4612
[22] Oxidative Aromatic C-O Bond Formation: Synthesis of 3-Functionalized Benzo[b]furans by FeCl3-Mediated Ring Closure of α-Aryl Ketones
Liang, Zhidan
Hou, Weizhe
Du, Yunfei
Zhang, Yongliang
Pan, Yan
Mao, Deng
Zhao, Kang
ORGANIC LETTERS, 2009, 11 (21) : 4978 - 4981
[23] Synthesis of novel benzo[b]furans and benzo[b]thiophenes: analogs of combretastatin and resveratrol
Chauhan, Jay
Monteil, Alexandre R.
Patterson, Steven E.
HETEROCYCLIC COMMUNICATIONS, 2010, 16 (4-6) : 241 - 244
[24] Iron and Copper Salts in the Synthesis of Benzo[b]furans
Bonnamour, Julien
Piedrafita, Maria
Bolm, Carsten
ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (10) : 1577 - 1581
[25] Zeolite-catalyzed synthesis of 2,3-unsubstituted benzo[b]furans via the intramolecular cyclization of 2-aryloxyacetaldehyde acetals
Sun, Nan
Huang, Peng
Wang, Yifan
Mo, Weimin
Hu, Baoxiang
Shen, Zhenlu
Hu, Xinquan
TETRAHEDRON, 2015, 71 (29) : 4835 - 4841
[26] Palladium-Catalyzed Oxidative Cycloisomerization of 2-Cinnamyl-1,3-Dicarbonyls: Synthesis of Functionalized 2-Benzyl Furans
Nallagonda, Rajender
Reddy, Reddy Rajasekhar
Ghorai, Prasanta
CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (42) : 14732 - 14736
[27] Efficient Synthetic Approach to Substituted Benzo[b]furans and Benzo[b]thiophenes by Iodine-Promoted Cyclization of Enaminones
Labarrios, Ehecatl
Jerezano, Alberto
Jimenez, Fabiola
del Carmen Cruz, Maria
Delgado, Francisco
Gerardo Zepeda, L.
Tamariz, Joaquin
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2014, 51 (04) : 954 - 971
[28] Facile synthesis of benzofurans via copper-catalyzed aerobic oxidative cyclization of phenols and alkynes
Zeng, Wei
Wu, Wanqing
Jiang, Huanfeng
Huang, Liangbin
Sun, Yadong
Chen, Zhengwang
Li, Xianwei
CHEMICAL COMMUNICATIONS, 2013, 49 (59) : 6611 - 6613
[29] Recent Development on the Synthesis of Benzo[b]- and Naphtho[b]furans: A Review
Kwiecien, Halina
Smist, Malgorzata
Kowalewska, Monika
CURRENT ORGANIC SYNTHESIS, 2012, 9 (04) : 529 - 560
[30] Synthesis of benzo[b]thiophenes by electrophilic cyclization
Larock, RC
Yue, DW
TETRAHEDRON LETTERS, 2001, 42 (35) : 6011 - 6013

← 1 2 3 4 5 →