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A regioselective approach to 5-substituted-3-amino-1,2,4-triazines. 2003
John Limanto, and
Richard A Desmond, and
Donald R Gauthier, and
Paul N Devine, and
Robert A Reamer, and
R P Volante
Department of Process Research, Merck Research Laboratories, Merck & Co., Inc., P.O. Box 2000, Rahway, NJ 07065, USA. john_limanto@merck.com
Nucleophilic displacement of readily available alpha,alpha-dibromoketones with excess morpholine gave the corresponding ketoaminals, which upon condensation with aminoguanidine in MeOH in the presence of AcOH afforded 5-substituted-3-amino-1,2,4-triazines in >95% regioselectivity and 45-76% isolated yield. [reaction: see text]
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