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使用乙烯基三氟硼酸钾合成2-取代的2H-色烯

Synthesis of 2-substituted 2H-chromenes using potassium vinyltrifluoroborates.

作者信息

Liu Fei, Evans Todd, Das Bhaskar C

机构信息

Department of Nuclear Medicine Albert Einstein College of Medicine, Bronx, NY 10461, United States.

出版信息

Tetrahedron Lett. 2008 Mar 3;49(10):1578-1581. doi: 10.1016/j.tetlet.2008.01.008.

DOI:10.1016/j.tetlet.2008.01.008
PMID:21753857
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC3132890/
Abstract

2H-Chromenes were synthesized from salicylaldehyde using potassium vinylic borates in the presence of secondary amines. We synthesized these 2H-chromene derivatives as a part of an ongoing project to develop inhibitors for TGF-β receptors. Potassium vinyl trifluoroborates react with salicylaldehydes at 80 °C in the presence of a secondary amine and produced 2-substituted 2H-chromene derivatives with a 70-90% yield.

摘要

在仲胺存在下,使用乙烯基硼酸酯钾从水杨醛合成了2H-色烯。作为正在进行的开发转化生长因子-β(TGF-β)受体抑制剂项目的一部分,我们合成了这些2H-色烯衍生物。乙烯基三氟硼酸钾在仲胺存在下于80℃与水杨醛反应,以70-90%的产率生成2-取代的2H-色烯衍生物。

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本文引用的文献

1
Enantioselective Synthesis and Photoracemization Studies of (+)-2-Cyclopropyl-7,8-dimethoxy-2- chromene-5-carboxylic Acid Methyl Ester, an Advanced Intermediate of a Dihydrofolate Reductase Inhibitor.二氢叶酸还原酶抑制剂的一种高级中间体(+)-2-环丙基-7,8-二甲氧基-2-色烯-5-羧酸甲酯的对映选择性合成及光消旋化研究
J Org Chem. 1999 Jul 9;64(14):5321-5324. doi: 10.1021/jo990352s.
2
Organotrifluoroborates: protected boronic acids that expand the versatility of the Suzuki coupling reaction.有机三氟硼酸盐:可扩展铃木耦合反应多功能性的保护硼酸酯。
Acc Chem Res. 2007 Apr;40(4):275-86. doi: 10.1021/ar050199q. Epub 2007 Jan 26.
3
Unexpected tandem ylide annulation reaction for controllable synthesis of 2H-chromenes and 4H-chromenes.用于可控合成2H-色烯和4H-色烯的意外串联叶立德环化反应
Org Lett. 2006 Aug 17;8(17):3853-6. doi: 10.1021/ol0615174.
4
Oxidation of hydroxyl-substituted organotrifluoroborates.羟基取代的有机三氟硼酸盐的氧化反应。
J Am Chem Soc. 2006 Aug 2;128(30):9634-5. doi: 10.1021/ja062974i.
5
Synthesis of functionalized organotrifluoroborates via halomethyltrifluoroborates.通过卤代甲基三氟硼酸盐合成功能化有机三氟硼酸盐。
Org Lett. 2006 May 11;8(10):2031-4. doi: 10.1021/ol060375a.
6
cis-dihydroxylation of unsaturated potassium alkyl- and aryltrifluoroborates.不饱和烷基和芳基三氟硼酸钾的顺式二羟基化反应
Org Lett. 2006 Jan 5;8(1):75-8. doi: 10.1021/ol052549e.
7
Expanding organoboron chemistry: epoxidation of potassium organotrifluoroborates.拓展有机硼化学:有机三氟硼酸钾的环氧化反应
J Am Chem Soc. 2003 Sep 17;125(37):11148-9. doi: 10.1021/ja0351140.
8
Regiospecific functionalization of methyl C-H bonds of alkyl groups in reagents with heteroatom functionality.在具有杂原子官能团的试剂中,烷基甲基C-H键的区域特异性官能化。
J Am Chem Soc. 2004 Dec 1;126(47):15334-5. doi: 10.1021/ja044933x.
9
Palladium-catalyzed cross-coupling of stereospecific potassium cyclopropyl trifluoroborates with aryl bromides.钯催化立体特异性环丙基三氟硼酸钾与芳基溴的交叉偶联反应。
Org Lett. 2004 Feb 5;6(3):357-60. doi: 10.1021/ol036184e.
10
Modern synthetic methods for copper-mediated C(aryl)[bond]O, C(aryl)[bond]N, and C(aryl)[bond]S bond formation.用于铜介导的C(芳基)-O键、C(芳基)-N键和C(芳基)-S键形成的现代合成方法。
Angew Chem Int Ed Engl. 2003 Nov 17;42(44):5400-49. doi: 10.1002/anie.200300594.