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A regioselective approach to 5-substituted-3-amino-1,2,4-triazines
John Limanto1, Richard A Desmond, Donald R Gauthier
1Department of Process Research, Merck Research Laboratories, Merck & Co., Inc., P.O. Box 2000, Rahway, NJ 07065, USA. john_limanto@merck.com
Organic Letters
|June 21, 2003
Abstract:
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]