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Synlett

Volumn , Issue 3, 2007, Pages 427-430

Palladium-catalyzed allylation of 2-hydroxy-1,4-naphthoquinone: Application to the preparation of lapachol

(3) Kazantzi, Georgia a Malamidou Xenikaki, Elizabeth a Spyroudis, Spyros a

a ARISTOTLE UNIVERSITY OF THESSALONIKI (Greece)

Author keywords

Allylation; Lapachol; Lawsone; Palladium catalyzed

Indexed keywords

1,4 NAPHTHOQUINONE DERIVATIVE; 2 (1,1 DIMETHYL 2 PROPENYL) 3 HYDROXY 1,4 NAPHTHOQUINONE; ALCOHOL DERIVATIVE; ESTER DERIVATIVE; LAPACHOL; LAWSONE; PALLADIUM; UNCLASSIFIED DRUG;

ALLYLATION; ARTICLE; BIOLOGICAL ACTIVITY; CATALYSIS; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS;

EID: 33847400102 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2007-967947 Document Type: Article

Times cited : (15)

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- General Procedure for the Allylation Reaction of Lawsone under Neat Conditions. A mixture of lawsone (157 mg, 0.9 mmol, Pd(Ph 3P)4 (50 mg, 0.045 mmol, AcOH (6 mg, 0.09 mmol, ca. 2 drops) and the proper allylating agent (alcohol or ester, 1.5 mmol) was thoroughly mixed and was put in an oven preheated at 100°C. After 35 min the gummy material was subjected to column chromatography (silica gel, hexane-EtOAc, 5:1) to afford the allyl derivatives 8a-e. Representative Data for Allylation Products. 2-Hydroxy-3-(3-phenylallyl)-1,4-naphthoquinone (8b, mp 168-170°C (lit.18 170°C, IR (KBr, v, 3289, 1671, 1641 cm-1. 1H NMR (300 MHz, CDCl3, δ, 8.14 (1 H, d, J, 7.3 Hz, 8.09 (1 H, d, J, 7.3 Hz, 7.77 (1 H, t, J, 7.3 Hz, 7.69 (1 H, t, J, 7.3 Hz, 7.41 (1 H, s, OH, 7.35-7.17 (5 H, m, 6.57 (1 H, d, J, 15.9 Hz, 6.30 1 H, dt, J1
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