One-pot synthesis of malononitriles by free radical reactions of ylidenemalononitrile with Et3B and iodoalkane in a water-ether biphase medium

Zhijay Tu; Chunchi Lin; Yaochung Jang; Yeong Jiunn Jang; Shengkai Ko; Hulin Fang; Ju Tsung Liu; Ching Fa Yao

doi:10.1016/j.tetlet.2006.06.061

One-pot synthesis of malononitriles by free radical reactions of ylidenemalononitrile with Et₃B and iodoalkane in a water-ether biphase medium

Zhijay Tu, Chunchi Lin, Yaochung Jang, Yeong Jiunn Jang, Shengkai Ko, Hulin Fang, Ju Tsung Liu, Ching Fa Yao^*

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

11 Citations (Scopus)

Abstract

The one-pot synthesis of malononitrile derivatives 4, 6, and 7 in moderate to high yields by the reaction of ylidenemalononitriles 3, prepared in situ from carbonyl compounds 1 and malononitrile 2 in the presence of ammonium acetate in aqueous solution at 50-60 °C, with Et₃B or RI 5/Et₃B in a water-diethyl ether biphase medium under an atmosphere of room temperature is reported. The reaction of Et₃B with adamantyl iodides 8 and 10 under similar conditions gave 9 and 11 in high yields, respectively. However, low yields of the monoalkylated combined with dialkylated malonates 14 were obtained when benzaldehyde 1a was condensed with dimethylmalonate 12 followed by parallel free radical treatment in benzene solution.

Original language	English
Pages (from-to)	6133-6137
Number of pages	5
Journal	Tetrahedron Letters
Volume	47
Issue number	34
DOIs	https://doi.org/10.1016/j.tetlet.2006.06.061
Publication status	Published - 2006 Aug 21

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2006.06.061

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@article{7d4b53a52fcc41e8b98050524e27b8c9,

title = "One-pot synthesis of malononitriles by free radical reactions of ylidenemalononitrile with Et3B and iodoalkane in a water-ether biphase medium",

abstract = "The one-pot synthesis of malononitrile derivatives 4, 6, and 7 in moderate to high yields by the reaction of ylidenemalononitriles 3, prepared in situ from carbonyl compounds 1 and malononitrile 2 in the presence of ammonium acetate in aqueous solution at 50-60 °C, with Et3B or RI 5/Et3B in a water-diethyl ether biphase medium under an atmosphere of room temperature is reported. The reaction of Et3B with adamantyl iodides 8 and 10 under similar conditions gave 9 and 11 in high yields, respectively. However, low yields of the monoalkylated combined with dialkylated malonates 14 were obtained when benzaldehyde 1a was condensed with dimethylmalonate 12 followed by parallel free radical treatment in benzene solution.",

author = "Zhijay Tu and Chunchi Lin and Yaochung Jang and Jang, {Yeong Jiunn} and Shengkai Ko and Hulin Fang and Liu, {Ju Tsung} and Yao, {Ching Fa}",

note = "Funding Information: Financial support of this work by the National Science Council of the Republic of China is gratefully acknowledged. ",

year = "2006",

month = aug,

day = "21",

doi = "10.1016/j.tetlet.2006.06.061",

language = "English",

volume = "47",

pages = "6133--6137",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "34",

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TY - JOUR

T1 - One-pot synthesis of malononitriles by free radical reactions of ylidenemalononitrile with Et3B and iodoalkane in a water-ether biphase medium

AU - Tu, Zhijay

AU - Lin, Chunchi

AU - Jang, Yaochung

AU - Jang, Yeong Jiunn

AU - Ko, Shengkai

AU - Fang, Hulin

AU - Liu, Ju Tsung

AU - Yao, Ching Fa

N1 - Funding Information: Financial support of this work by the National Science Council of the Republic of China is gratefully acknowledged.

PY - 2006/8/21

Y1 - 2006/8/21

N2 - The one-pot synthesis of malononitrile derivatives 4, 6, and 7 in moderate to high yields by the reaction of ylidenemalononitriles 3, prepared in situ from carbonyl compounds 1 and malononitrile 2 in the presence of ammonium acetate in aqueous solution at 50-60 °C, with Et3B or RI 5/Et3B in a water-diethyl ether biphase medium under an atmosphere of room temperature is reported. The reaction of Et3B with adamantyl iodides 8 and 10 under similar conditions gave 9 and 11 in high yields, respectively. However, low yields of the monoalkylated combined with dialkylated malonates 14 were obtained when benzaldehyde 1a was condensed with dimethylmalonate 12 followed by parallel free radical treatment in benzene solution.

AB - The one-pot synthesis of malononitrile derivatives 4, 6, and 7 in moderate to high yields by the reaction of ylidenemalononitriles 3, prepared in situ from carbonyl compounds 1 and malononitrile 2 in the presence of ammonium acetate in aqueous solution at 50-60 °C, with Et3B or RI 5/Et3B in a water-diethyl ether biphase medium under an atmosphere of room temperature is reported. The reaction of Et3B with adamantyl iodides 8 and 10 under similar conditions gave 9 and 11 in high yields, respectively. However, low yields of the monoalkylated combined with dialkylated malonates 14 were obtained when benzaldehyde 1a was condensed with dimethylmalonate 12 followed by parallel free radical treatment in benzene solution.

UR - http://www.scopus.com/inward/record.url?scp=33745997331&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=33745997331&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2006.06.061

DO - 10.1016/j.tetlet.2006.06.061

M3 - Article

AN - SCOPUS:33745997331

SN - 0040-4039

VL - 47

SP - 6133

EP - 6137

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 34

ER -

One-pot synthesis of malononitriles by free radical reactions of ylidenemalononitrile with Et₃B and iodoalkane in a water-ether biphase medium

Abstract

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