Solid phase synthesis of 3-(5-arylpyridin-2-yl)-4-hydroxycoumarins

Yannan Liu; Aaron D. Mills; Mark J. Kurth

doi:10.1016/j.tetlet.2006.01.069

Solid phase synthesis of 3-(5-arylpyridin-2-yl)-4-hydroxycoumarins

Yannan Liu, Aaron D. Mills, Mark J. Kurth

Chemistry

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12 Scopus citations

Abstract

A solid phase strategy has been developed for the synthesis of 3-(5-arylpyridin-2-yl)-4-hydroxycoumarins. The key transformation is an intramolecular ipso substitution reaction which forms the coumarin heterocycle and culminates with cleavage of product from the polymer support. The pyridine moiety at C3 can be further modified with Suzuki coupling. A sample library with two diversity elements has been synthesized to demonstrate this ipso substation-based cyclo-elimination strategy.

Original language	English (US)
Pages (from-to)	1985-1988
Number of pages	4
Journal	Tetrahedron Letters
Volume	47
Issue number	12
DOIs	https://doi.org/10.1016/j.tetlet.2006.01.069
State	Published - Mar 20 2006

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ASJC Scopus subject areas

Biochemistry
Organic Chemistry
Drug Discovery

Cite this

Liu, Y., Mills, A. D., & Kurth, M. J. (2006). Solid phase synthesis of 3-(5-arylpyridin-2-yl)-4-hydroxycoumarins. Tetrahedron Letters, 47(12), 1985-1988. https://doi.org/10.1016/j.tetlet.2006.01.069

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AB - A solid phase strategy has been developed for the synthesis of 3-(5-arylpyridin-2-yl)-4-hydroxycoumarins. The key transformation is an intramolecular ipso substitution reaction which forms the coumarin heterocycle and culminates with cleavage of product from the polymer support. The pyridine moiety at C3 can be further modified with Suzuki coupling. A sample library with two diversity elements has been synthesized to demonstrate this ipso substation-based cyclo-elimination strategy.

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10.1016/j.tetlet.2006.01.069