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Synlett

Volumn , Issue 15, 2008, Pages 2317-2320

Efficient condensation between glyoxal hydrates and sulfonium salts leading to highly functionalized 1,4-diketones

(2) Shao, Qiyun a Li, Chunbao a

a TIANJIN UNIVERSITY (China)

Author keywords

Alkenes; Catalysis; Condensation; Selenium; Sulfur

Indexed keywords

ALPHA ALKYLTHIO ALPHA,BETA 1,4 DICARBONYL DERIVATIVE; CARBONYL DERIVATIVE; GLYOXAL DERIVATIVE; GLYOXAL HYDRATE DERIVATIVE; SELENATE; SELENIUM DERIVATIVE; SELENIUM OXIDE; SODIUM CARBONATE; SULFONIUM DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL STRUCTURE; DEALKYLATION; ELIMINATION REACTION; POLYMERIZATION; SUBSTITUTION REACTION;

EID: 53149109701 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2008-1078267 Document Type: Article

Times cited : (12)

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- Typical Procedure for Preparing Compound 3 A mixture of 1a (152 mg, 1.0 mmol, 2a (261 mg, 1.0 mmol, SeO2 (4.4 mg, 0.04 mmol, and Na2CO3 (10.6 mg, 0.1 mmol) in MeCN (10 mL) was stirred for 4.5 h at r.t. After complete consumption of starting material (TLC, MeCN was removed in vacuum to give yellow syrup. The residue was extracted with CH2Cl2 (2 x 30 mL, The combined organic layers were washed with brine (10 mL) and dried over anhyd Na2SO4. The extracts were then concentrated under reduced pressure, and the residue was purified by column chromatography (eluent: PE-EtOAc) on SiO2 to give an 81% yield of 3a, Z)-3a, 129 mg; (E)-3a, 100 mg, Compound (Z)-3a: 1H NMR (400 MHz, CDCl 3, δ, 8.08 (d, J, 8.5 Hz, 2 H, 7.95 (d, J, 8.5 Hz, 2 H, 7.69-7.44 (m, 6 H, 7.10 (s, 1 H, 2.17 s, 3 H
- 3

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