Bioorganic & Medicinal Chemistry Letters 2005-02-01

A convenient one-pot synthesis of asymmetric 1,3,5-triazine-2,4,6-triones and its application towards a novel class of gonadotropin-releasing hormone receptor antagonists.

Zhiqiang Guo, Dongpei Wu, Yun-Fei Zhu, Fabio C Tucci, Joseph Pontillo, John Saunders, Qiu Xie, R Scott Struthers, Chen Chen

Index: Bioorg. Med. Chem. Lett. 15(3) , 693-8, (2005)

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Abstract

A convenient one-pot synthetic route was developed for the preparation of asymmetric 1,3-dialkyl-1,3,5-triazine-2,4,6-triones from readily available alkyl- or aryl-isocyanates, primary amines and N-chlorocarbonyl isocyanate in excellent yields. Subsequent alkylation with N-protected amino alcohols afforded the desired 1,3,5-triazine-2,4,6-triones in good yields. This methodology was applied to the synthesis of a chemical library acting as antagonists of the hGnRH receptor.