A new method using 2-chloro-4,6-dimethoxy-1,3,5-triazine for facile elimination of dimethylamino group in Eschenmoser's methylenation for synthesis of α,β-unsaturated esters

被引：16

作者：

Yamada, Kohei ^{[1
]}

Masaki, Kazumasa ^{[1
]}

Hagimoto, Yuri ^{[2
]}

Kamiya, Seina ^{[3
]}

Kunishima, Munetaka ^{[1
,2
]}

机构：

[1] Kanazawa Univ, Inst Med Pharmaceut & Hlth Sci, Fac Pharmaceut Sci, Kanazawa, Ishikawa 9201192, Japan

[2] Kobe Gakuin Univ, Cooperat Res Ctr Life Sci, Chuo Ku, Kobe, Hyogo 6558586, Japan

[3] Kobe Gakuin Univ, Fac Pharmaceut Sci, Chuo Ku, Kobe, Hyogo 6558586, Japan

来源：

TETRAHEDRON LETTERS | 2013年 / 54卷 / 13期

关键词：

Eschenmoser's methylenation; 2-Chloro-4,6-dimethoxy-1,3,5-triazine (CDMT); alpha; beta-Unsaturated esters; DEHYDROCONDENSATION; INTERFACE; MICELLES; CHLORIDE; AMIDES; ACIDS;

D O I：

10.1016/j.tetlet.2013.01.092

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A facile one-step method for the elimination of the dimethylamino group in Eschenmoser's methylenation has been developed using a combination of 2-chloro-4,6-dimethoxy-1,3,5-triazine and triethylamine. The chemoselective elimination of the dimethylamino group occurred in compounds possessing either a diethylamino group or an alkylsulfanyl group. (C) 2013 Elsevier Ltd. All rights reserved.

引用

页码：1758 / 1760

页数：3

共 3 条

[1] A caveat on the use of 2-chloro-4,6-dimethoxy-1,3,5-triazine for the synthesis of 4,4-dimethyl-2-R-2-oxazolines
Gossage, RA
Sadowy, AL
LETTERS IN ORGANIC CHEMISTRY, 2005, 2 (01) : 25 - 28
[2] Fluorous coupling reagents: Application of 2-chloro-4,6-bis[(heptadecafluorononyl)oxy]-1,3,5-triazine in peptide synthesis
Markowicz, MW
Dembinski, R
SYNTHESIS-STUTTGART, 2004, (01): : 80 - 86
[3] A Simple Practical Method for the Synthesis of 4,6-Dimethoxy-1,3,5-triazin-2(1H)-one Using Dimethylamine-Functionalized Solid-Phase Reagents
Hioki, Kazuhito
Ohshima, Kelichi
Sota, Yuko
Tanaka, Miki
Kunishima, Munetaka
SYNTHESIS-STUTTGART, 2009, (04): : 542 - 544

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