General and Rapid Pyrimidine Condensation by Addressing the Rate Limiting Aromatization
…, S Sanyal, KR Fandrick, S Ma, N Grinberg, H Lee…
Index: Fandrick, Daniel R.; Reinhardt, Delia; Desrosiers, Jean-Nicolas; Sanyal, Sanjit; Fandrick, Keith R.; Ma, Shengli; Grinberg, Nelu; Lee, Heewon; Song, Jinhua J.; Senanayake, Chris H. Organic Letters, 2014 , vol. 16, # 11 p. 2834 - 2837
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Citation Number: 8
Abstract
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 ...
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