General and Rapid Pyrimidine Condensation by Addressing the Rate Limiting Aromatization
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- 作者：Daniel R. Fandrick ; Delia Reinhardt ; Jean-Nicolas Desrosiers ; Sanjit Sanyal ; Keith R. Fandrick ; Shengli Ma ; Nelu Grinberg ; Heewon Lee ; Jinhua J. Song ; Chris H. Senanayake
- 刊名：Organic Letters
- 出版年：2014
- 出版时间：June 6, 2014
- 年：2014
- 卷：16
- 期：11
- 页码：2834-2837
- 全文大小：349K
- 年卷期：v.16,no.11(June 6, 2014)
- ISSN：1523-7052
文摘
The rate limiting aromatization within the condensation approach toward pyrimidines utilizing amidines and activated olefins was addressed to provide for a general and rapid process. A strong solvent effect was elucidated to affect the rate for the initial alkoxide elimination from the intermediate Michael adduct wherein polar aprotic solvents demonstrate an addition controlled aromatization. Spectroscopic studies support a solvent dependent equilibrium between the amidine and alkoxide base wherein the rate for aromatization is optimal when the equilibrium toward the amidine anion was strongly favored.