Temperature-controlled divergent synthesis of 4-alkoxy- or 4-alkenyl-chromanes via inverse electron-demand cycloaddition with in situ generated ortho-quinone methides

被引：16

作者：

Tanaka, Kenta ^{[1
]}

Kishimoto, Mami ^{[1
]}

Hoshino, Yujiro ^{[1
]}

Honda, Kiyoshi ^{[1
]}

机构：

[1] Yokohama Natl Univ, Grad Sch Environm & Informat Sci, Hodogaya Ku, Yokohama, Kanagawa 2408501, Japan

来源：

TETRAHEDRON LETTERS | 2018年 / 59卷 / 19期

关键词：

Divergent synthesis; Chromanes; ortho-Quinone methide; Inverse-electron-demand cycloaddition; FACILE SYNTHESIS; INTRAMOLECULAR CYCLOADDITION; OXIDATIVE CYCLIZATION; O-QUINONEMETHIDES; DERIVATIVES; PRINCIPLE; PROPERTY; INDOLE; AMIDES; BONDS;

D O I：

10.1016/j.tetlet.2018.03.090

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The temperature-controlled divergent synthesis of 4-alkoxy- or 4-alkenyl-chromanes via inverse electron-demand cycloaddition with in situ generated ortho-quinone methides under identical reaction conditions except for thermal condition has been developed. At room temperature, the reaction generated 4-methoxychromanes, whereas the reaction performed at room temperature to 100 degrees C gave 4-alkenylchromanes. Trifluoromethanesulfonic acid was efficiently suitable in the reaction to give the 4-substituted chromanes. This divergent synthetic strategy exhibits a new method giving carbon-carbon or carbon oxygen bond by controlling the reaction temperature. (C) 2018 Elsevier Ltd. All rights reserved.

引用

页码：1841 / 1845

页数：5

共 24 条

[21] Inverse-electron-demand [4+2] cycloaddition of photogenerated aza-ortho-quinone methides with 1,3,5-triazinanes: access to perfluoroalkylated tetrahydroquinazolines
Liang, Dong
Tan, Li-Ping
Xiao, Wen-Jing
Chen, Jia-Rong
CHEMICAL COMMUNICATIONS, 2020, 56 (26) : 3777 - 3780
[22] Facile Synthesis of Silylated 4,5-Disubstituted Phthalates via Inverse Electron-demand Cycloaddition of 2-Pyrone-4,5-dicarboxylate with Silylacetylenes
Hoshino, Yujiro
Ikeda, Yoshitaka
Nakai, Yota
Honda, Kiyoshi
CHEMISTRY LETTERS, 2017, 46 (12) : 1743 - 1746
[23] Highly regioselective synthesis of 2,3-disubstituted 2H-1-benzopyrans: Bronsted acid catalyzed [4+2] cycloaddition reaction with a variety of arylalkynes via ortho-quinone methides
Tanaka, Kenta
Sukekawa, Mayumi
Shigematsu, Yosuke
Hoshino, Yujiro
Honda, Kiyoshi
TETRAHEDRON, 2017, 73 (45) : 6456 - 6464
[24] Reaction of Push-Pull Enaminoketones and in Situ Generated ortho-Quinone Methides: Synthesis of 3-Acyl-4H-chromenes and 2-Acy1-1H-benzo[f]chromenes as Precursors for Hydroxybenzylated Heterocycles
Lukashenko, Anton V.
Osyanin, Vitaly A.
Osipov, Dmitry V.
Klimochkin, Yuri N.
JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (03): : 1517 - 1528

← 1 2 3 →