The first example of the 1-chalcogene-substituted formylolefination of the ketones and aldehydes using 1-lithio-2-ethoxyvinyl chalcogenides

被引：20

作者：

Yoshimatsu, M ^{[1
]}

Oguri, K ^{[1
]}

Ikeda, K ^{[1
]}

Gotoh, S ^{[1
]}

机构：

[1] Gifu Univ, Fac Engn, Dept Chem, Gifu 50111, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1998年 / 63卷 / 13期

关键词：

D O I：

10.1021/jo980487i

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The alpha-chalcogene-substituted formylolefinations of ketones and aldehydes proceeded using 1-lithio-2-ethoxyvinyl chalcogenides/PPSE or TMSOTf produce the alpha-chalcogenoformylolefinated products 4a-1 in high yields. Tandem-formylolefination provided the (2Z,4Z)-2,4-bis(chalcogeno)pent-2,4-dienals 5d,h,i and (2Z,4Z,6Z)-2,4,6-tris(phenylthio)hept-2, derivatives 7d and 8d, respectively.

引用

页码：4475 / 4480

页数：6

共 34 条

[21] Naphthyridines. Part 3: First example of the polyfunctionally substituted 1,2,4-triazolo[1,5-g][1,6]naphthyridines ring system
Mekheimer, Ramadan Ahmed
Ibrahim, Yusria Rizk
Ahmed, Eltaib Ali
Frey, Wolfgang
TETRAHEDRON, 2009, 65 (47) : 9843 - 9849
[22] An Efficient Oxidative Conversion of Aldehydes into 2-Substituted 2-Oxazolines Using 1,3-Diiodo-5,5-dimethylhydantoin
Takahashi, Shogo
Togo, Hideo
SYNTHESIS-STUTTGART, 2009, (14): : 2329 - 2332
[23] DIRECT OXIDATIVE CONVERSION OF ALDEHYDES INTO 2-SUBSTITUTED 1,4,5,6-TETRAHYDROPYRIMIDINES USING MOLECULAR IODINE OR 1,3-DIIODO-5,5-DIMETHYLHYDANTOIN
Takahashi, Shogo
Togo, Hideo
HETEROCYCLES, 2010, 82 (01) : 593 - 601
[24] PALLADIUM-CATALYZED VINYL SUBSTITUTION-REACTIONS .1. NEW SYNTHESIS OF 2-PHENYL AND 3-PHENYL SUBSTITUTED ALLYLIC ALCOHOLS, ALDEHYDES, AND KETONES FROM ALLYLIC ALCOHOLS
CHALK, AJ
MAGENNIS, SA
JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (02): : 273 - 278
[25] Atom transfer radical polymerization of 1,3-butadiene using CuBr/alkyl pyridine-2-carboximidate catalysts: The first example
Heo, SU
Lee, DW
JOURNAL OF INDUSTRIAL AND ENGINEERING CHEMISTRY, 2005, 11 (06) : 911 - 917
[26] Pt- and Au-catalyzed oxidative cyclization of 2-ethenyl-1-(prop-2′-yn-1-′-ol) benzenes to naphthyl aldehydes and ketones:: catalytic oxidation of metal-alkylidene intermediates using H2O and H2O2
Taduri, Bhanu Pratap
Abu Sohel, Shariar Md.
Cheng, Hsin-Mei
Lin, Guan-You
Liu, Rai-Shung
CHEMICAL COMMUNICATIONS, 2007, (24) : 2530 - 2532
[27] CONDENSATION OF THE ETHYL-ESTER OF 4-METHYL-2-OXO-2H-1-BENZOPYRAN-3-CARBOXYLIC ACID WITH ALDEHYDES AND KETONES - SYNTHESIS OF 2-SUBSTITUTED 4,5-DIOXO-1,2-DIHYDRO-4H,5H-PYRANO[3,4-C][1]-BENZOPYRANS
IVANOV, C
ANGHELOVA, Y
SPIROVA, S
SYNTHESIS-STUTTGART, 1979, (09): : 732 - 733
[28] Sodium hydroxide-promoted reaction of 1-substituted 2,3,3-trifluoroprop-1-enyl toluene-p-sulfonates with alcohols. First efficient and convenient access to ct-fluoro- QQ , QQ -dialkoxy ketones
J Chem Soc Perkin Trans 1, 18 (2679):
[29] Mass spectra of new functionally substituted heterocycles:: V.: First example of McLafferty rearrangement in the series of 5-(1-ethoxyethoxy)-2,3-dihydropyridines and 3-(1-ethoxyethoxy)pyridines derived from α-lithiated 1-(1-ethoxyethoxy)-allene and methoxymethyl isothiocyanate
Klyba, LV
Nedolya, NA
Shlyakhtina, NI
Zhanchipova, ER
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 41 (10) : 1544 - 1550
[30] Mass Spectra of New Functionally Substituted Heterocycles: V. First Example of McLafferty Rearrangement in the Series of 5-(1-Ethoxyethoxy)-2,3-dihydropyridines and 3-(1-Ethoxyethoxy)pyridines Derived from α-Lithiated 1-(1-Ethoxyethoxy)allene and Methoxymethyl Isothiocyanate
L. V. Klyba
N. A. Nedolya
N. I. Shlyakhtina
E. R. Zhanchipova
Russian Journal of Organic Chemistry, 2005, 41 : 1544 - 1550

← 1 2 3 4 →