An expedient and divergent tandem one-pot synthesis of pyrimidin-2,4-diones using the blaise reaction intermediate

Yu Sung Chun; Zi Xuan; Ju Hyun Kim; Sang Gi Lee

doi:10.1021/ol401389j

An expedient and divergent tandem one-pot synthesis of pyrimidin-2,4-diones using the blaise reaction intermediate

Yu Sung Chun, Zi Xuan, Ju Hyun Kim, Sang Gi Lee

Department of Chemistry & Nanoscience

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

31 Scopus citations

Abstract

A novel divergent tandem one-pot method for the synthesis of 3,5,6-trisubstituted 1H-pyrimidin-2,4-dione derivatives is developed. In the presence of 10 mol % of Cu(OAc)₂, the α-substituted Blaise reaction intermediates (R² ≠ H) reacted with isocyanates chemoselectively to afford pyrimidin-2,4-diones, whereas the α-unsubstituted Blaise reaction intermediate (R² = H) showed a propensity to be a C-nucleophile toward electrophiles, permitting the installation of different functionalities at the 5-position through sequential tandem reactions.

Original language	English
Pages (from-to)	3162-3165
Number of pages	4
Journal	Organic Letters
Volume	15
Issue number	12
DOIs	https://doi.org/10.1021/ol401389j
State	Published - 21 Jun 2013

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title = "An expedient and divergent tandem one-pot synthesis of pyrimidin-2,4-diones using the blaise reaction intermediate",

abstract = "A novel divergent tandem one-pot method for the synthesis of 3,5,6-trisubstituted 1H-pyrimidin-2,4-dione derivatives is developed. In the presence of 10 mol % of Cu(OAc)2, the α-substituted Blaise reaction intermediates (R2 ≠ H) reacted with isocyanates chemoselectively to afford pyrimidin-2,4-diones, whereas the α-unsubstituted Blaise reaction intermediate (R2 = H) showed a propensity to be a C-nucleophile toward electrophiles, permitting the installation of different functionalities at the 5-position through sequential tandem reactions.",

author = "Chun, {Yu Sung} and Zi Xuan and Kim, {Ju Hyun} and Lee, {Sang Gi}",

year = "2013",

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doi = "10.1021/ol401389j",

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journal = "Organic Letters",

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T1 - An expedient and divergent tandem one-pot synthesis of pyrimidin-2,4-diones using the blaise reaction intermediate

AU - Chun, Yu Sung

AU - Xuan, Zi

AU - Kim, Ju Hyun

AU - Lee, Sang Gi

PY - 2013/6/21

Y1 - 2013/6/21

N2 - A novel divergent tandem one-pot method for the synthesis of 3,5,6-trisubstituted 1H-pyrimidin-2,4-dione derivatives is developed. In the presence of 10 mol % of Cu(OAc)2, the α-substituted Blaise reaction intermediates (R2 ≠ H) reacted with isocyanates chemoselectively to afford pyrimidin-2,4-diones, whereas the α-unsubstituted Blaise reaction intermediate (R2 = H) showed a propensity to be a C-nucleophile toward electrophiles, permitting the installation of different functionalities at the 5-position through sequential tandem reactions.

AB - A novel divergent tandem one-pot method for the synthesis of 3,5,6-trisubstituted 1H-pyrimidin-2,4-dione derivatives is developed. In the presence of 10 mol % of Cu(OAc)2, the α-substituted Blaise reaction intermediates (R2 ≠ H) reacted with isocyanates chemoselectively to afford pyrimidin-2,4-diones, whereas the α-unsubstituted Blaise reaction intermediate (R2 = H) showed a propensity to be a C-nucleophile toward electrophiles, permitting the installation of different functionalities at the 5-position through sequential tandem reactions.

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EP - 3165

JO - Organic Letters

JF - Organic Letters

IS - 12

ER -

An expedient and divergent tandem one-pot synthesis of pyrimidin-2,4-diones using the blaise reaction intermediate

Abstract

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